• When was the last time you met with your manager? With your direct reports?

• Do you know what or where they want to be in a few years?

• Do they know what’s holding them back from hitting the next level?

• Do you have a light plan for supporting them to get to that next level?

• Do you have a reliable place for them to raise concerns privately?

• Do they know what good performance looks like?

• Would they be surprised by your current assessment of their performance?

• Do you know what is making their job harder?

• Do you follow through on the commitments you make to them?

• When was the last time you canceled and failed to reschedule?

There’s no judgement. Just give yourself an honest yes/no.

Why Care About This?

A 1:1 is a recurring private conversation between a manager and an employee about how work is going, what support they need, how they are performing, what is getting in their way, and where they want to grow.

It is not a status meeting, a manager monologue, a performance review, or a social visit.

High-quality 1:1s are an evidence-backed, highly relational management practice. When they are done reasonably well, employees are more likely to speak up, seek and learn from feedback, feel supported, remain engaged, and perform better. [1, 2, 4, 5, 6, 8]

Not a 1:1 person?

Maybe you walk around and talk to people informally and think that is good enough.

Walking around is useful. Hallway conversations matter.

They are not the same thing as protected time.

Informal access tends to favor whoever is loudest, closest, most comfortable interrupting you, or best connected to the office grapevine. A recurring private conversation gives everyone access, including the quiet expert, the new employee, the remote worker, and the person who does not feel comfortable announcing a problem in front of six other people.

Research on employee silence tells us people weigh the interpersonal cost of speaking before offering bad news, disagreement, or criticism. Psychological safety and the quality of the manager–employee relationship determines whether they speak up. [4, 5, 7, 9]

When employees lack reliable access to individualized conversations with their manager, organizations risk weaker psychological safety, more withheld bad news, poorer feedback, missed development, and weaker manager–employee relationships. [4, 5, 6, 7, 8]

Look, the direct research on 1:1s is still in progress. There are not dozens of experiments across different work domains randomly assigning people to weekly, monthly, or nonexistent meetings. What is published includes an unusually large randomized intervention, a two-wave employee study, and emerging cross-sectional evidence. [1, 2, 3]

The rest of the argument comes from several mature bodies of research that agrees: psychological safety, employee voice, feedback, supervisor support, coaching, listening, and relationship quality.

I don’t have perfect proof of a universal 1:1 formula.

I do have enough evidence to help us take the practice seriously.

The First One

When you first join a team, do a round of 1:1s with everyone.

20-60 minutes per person. One goal: get to know them. No hidden agenda. No surprise performance conversations.

There are location dependent power dynamics, so, let them choose. Where possible provide options for a private, neutral, accessible location.

Let the employee choose between an office, conference room, virtual call, or walk outside. Do not assume walking is comfortable, accessible, private, or culturally preferable.

Make sure you show up!

Then, just talk and listen.

Get curious.

If you need some help here are some starter questions.

1. How long have you worked here?

2. What aspects of your job do you like and dislike?

3. What do you enjoy outside of work?

4. What do you do for fun?

5. How’s work going?

6. What kind of music do you like?

7. Read any good books lately?

8. Watched anything good recently?

9. Favorite flavor of ice cream?

10. What’s your relationship with your mother like and how does that show up in your trauma patterns and shame responses?

Keep is casual.

Don’t take notes on your first 1:1. But do write down some observations afterwards. Things like:

• Favorite snack.

• Whether they seem energized or not. (Not to diagnose, but to understand if you just took the helm of an entire team of burnt out zombies who need help asap.)

• If you share something in common.

• Maybe something you can ask about in the hallway!

  • e.g. “Hey Chad, how was the fishing trip with the family last weekend?”

The tiny follow ups signal:

I remember what you told me.

Sometimes people are skittish to volunteer information. If you see this being the case, model opening up about your own life and volunteer some information before asking them to do the same.

Vulnerability doesn’t require a dramatic confession. Just some openness and common ground.

The Habit

Frequency

The literature says

• 1:1s need regularity to maintain continuity.

• Quality matters more than frequency.

• Focusing on employee needs improves psychological safety.

• Exact prescriptions for cadence and duration are unproven!

Twice a year isn’t enough. Once a quarter is pushing it. Depending on the team, once every two months or monthly may be good. Kim Scott recommends weekly in Radical Candor.

In my experience, it depends on the team, the task, and what they need.

It’s about them. Not you.

And there is no one prescription that works.

So, be a scientist and experiment!

Try weekly for a month. Try monthly for a quarter.

Ask your team which they like better.

Wash, rinse, repeat.

Agenda

There are a couple schools of thought here.

Some say you should always present an agenda to reduce employee anxiety (I’ll have a sample below).

Others say the 1:1 is for the employee so they need to bring the agenda.

Science says you want a mix. Employee should own the first 2/3, you own 2/9, and the last 1/9 is closing and commitments.

Employee Topics

This is up to them! Just listen. If you need to warm it up here are some questions that dig into how things are going.

Your goal isn’t to ask all of these… it’s to figure out how you can support them.

• What is going well?

• What’s dragging lately?

• Are you stuck anywhere and can I help you get unstuck?

• Are there any decisions you need from me to keep your work going?

• Do you feel you have clear priorities on what’s important?

• Is there anything you have been hesitant to raise that you want to bring up?

• What do you think am I not seeing as much lately?

Manager Topics

Your portion could include:

• Recognition for specific work or behavior.

• Clarification of priorities or expectations, as needed.

• Specific, behavior-based feedback, as needed.

• Concerns that should be addressed before they become formal problems.

• What can I do to support you better?

• Is there anything I can do to improve as your manager?

Give kudos liberally, but mean them.

Understand that feedback is not automatically helpful.

The largest known feedback meta-analysis ever showed that more than one third of feedback interventions harmed performance. Feedback is dangerous when it redirects attention away from the task and towards identity defense. [15]

Stay grounded in emphasizing the desired future action. [16]

The credibility, supportiveness, and usefulness of your feedback influences whether it lands for the receiver. [17]

People are more likely to seek feedback if the relationship feels supportive. [18]

If you don’t have their priorities, performance standards, and behavior expectations written down you can’t just give feedback willy-nilly based on your own judgment. You need to have a contract somewhere before you can hold people to it.

Build the system, make the bar known, then coach people to get there.

Water your plants

Here’s a few more and I’d sprinkle these in throughout the year to ensure you’re helping them develop professionally. These are in context of the “What’s your professional goal right now?” north star. If you don’t have that defined, get there first, then ask these.

• Is there any work would you like more exposure to?

• Where would you want more independence?

• Is there an assignment, introduction, or practice opportunity I can provide?

• What is your professional goal right now?

• What progress do you want to see this year?

You do not need to ask these questions every week.

You do need to ask them often enough that employee development does not appear only during annual reviews, promotion disputes, and resignation conversations.

Coaching research generally finds positive effects, particularly on behavior, but it also finds that simply accumulating more sessions does not guarantee better outcomes. [19, 20]

Quality attention matters more than big calendar blocks.

Closing

End by creating continuity! Write your notes down into a shared document or a response to an ongoing email chain.

WRITE. IT. DOWN.

Make sure they have it.

• What did we decide?

• Who owns each next step?

• What do I owe you?

• What do you owe me?

• Is there any feedback you’re going to work on between now and next meeting?

• Is there any feedback you gave me I’m going to work on?

• Do we need to meet again soon to discuss anything important?

Listening matters. Employees who believe their supervisors genuinely listen report less emotional exhaustion, lower intentions to leave, and more voluntary helpful behavior at work. [21]

But employees do not experience listening as a collection of theatrical techniques.

They experience it as a larger package that includes attention, trust, humility, respect, credibility, and follow-through. [22]

All listening without follow through is what rocks do. Literally a boulder. Piece of granite. That’s you dude. You’re a rock.

What a 1:1 is NOT

A 1:1 is not:

• A task-list recital.

• A substitute for timely feedback.

• A disciplinary ambush.

• A therapy session.

• A place to collect gossip.

• A manager monologue.

• A weekly demand that the employee prove productivity.

• A conversation where every concern immediately becomes an investigation.

• A promise that everything said will remain confidential regardless of content.

When things get rough

If you create a space where people feel safe telling the truth, eventually someone will tell you a truth that is heavy.

What do you do when someone is having a crisis in your office?

I don’t have all the answers, but I know this:

You’re not responsible for a diagnosis, therapy, or determining their ‘stability.’

Your job is to show up human:

1. Listen. Hard. Attentively. Present. Body facing them. PC screen off.

2. I try and take a step back and evaluate, are they at risk of harming themselves or others?

3. I gently ask some questions to figure out if the person has a support network.

Sometimes they just need someone to listen.

Sometimes it is clearly bigger than a bad day. That is when I privately offer whatever resources I know are available.

Remember, you’re a coach.

Your players are with you for years. If they have something going on now the best thing you can do is invest in their recovery so they are good to go a year from now, two years from now, etc.

Now, if there’s a safety risk, you have to go all in. Get someone qualified involved.

What I do

I have a couch in my office.

I offer snacks/tea when people come to visit. I keep some ice cream bars in my mini-freezer for when someone gets a well-earned win.

I want people to know they can come in and sit down for a few minutes. That they are welcome.

That they belong.

I have a shared 1:1 meeting minutes and performance document for every employee and I pull that up and add notes whenever we meet.

I have a team of 20+ and aim for monthly 1:1s with most of them. A few experienced employees prefer something closer to quarterly and already have easy access to me between meetings.

It’s never one-size fits all.

My door stays open and I close it for a few hours every day for deep work.

Availability matters to me. Manufacturing demands accessibility.

Boundaries also matter.

It’s a balance.

The same thing, again and again

I’ve been part-of and led leadership teams where we did extensive employee feedback canvassing. Then we sit down for days at a time to figure out how to solve the issues employees raised.

Action plans. RACI matrices. Sticky notes. Categories. Owners. Follow up meetings.

I always wonder when we go down that road:

Every time, bringing the organization a structured expectation for managers to do regular 1:1s with their teams improved the intangible gravity metrics of the org. Trust, psychological safety, openness and transparency. Feelings of being listened to and belonging. Engagement.

Supervisor support shapes whether employees feel valued by the organization. [4, 5, 6, 7, 8]

These things are difficult to place neatly on a dashboard.

They determine whether people tell you the truth.

Whether they ask for help.

Whether they admit mistakes.

Whether they know what you expect.

Whether they stay long enough to become excellent.

You don’t need a perfect template.

Create space and show up.

The Updraft is my archives for management tools, tips, and interviews with other leaders. Always free. Always for the people who are ready to grow.

Stick around. There’s more to come.

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References

[1] Castro, Silvia, Florian Englmaier, and Maria Guadalupe. Fostering Psychological Safety in Teams: Evidence from an RCT. CEPR Discussion Paper 20218. Paris and London: CEPR Press, 2025.

• Studied more than 500 teams and 4,300 employees observationally and randomized more than 1,000 teams and 7,000 employees, finding that employee-needs-focused manager conversations improved psychological safety, perceived leadership quality, and innovativeness.

[2] Flinchum, Jonathan R. A New Approach to Promote Employee Engagement: One-on-One Meetings Between Managers and Direct Reports. PhD diss., University of North Carolina at Charlotte, 2022.

• Surveyed 303 employees twice and found that relations-oriented 1:1 quality predicted engagement more strongly than frequency, although the benefits appeared only when meetings occurred at least approximately monthly.

[3] Taguchi, Yoto, Hiroko Kitamura, Yoshiyuki Shibata, Hisashi Eguchi, and Shoko Kawanami. “P-175 A Cross-Sectional Study of the Effects of Regular One-on-One Meetings Between Supervisors and Subordinates in the Workplace.” Occupational Medicine 74, suppl. 1 (2024), abstract P-175. doi:10.1093/occmed/kqae023.0705.

• Received 677 responses from 2,376 eligible employees and found that five or more 1:1s per year were associated with greater psychological safety but not clearly better mental health.

[4] Frazier, M. Lance, Stav Fainshmidt, Ryan L. Klinger, Amir Pezeshkan, and Veselina Vracheva. “Psychological Safety: A Meta-Analytic Review and Extension.” Personnel Psychology 70, no. 1 (2017): 113–65. doi:10.1111/peps.12183.

• Synthesized 136 samples, more than 22,000 people, and approximately 5,000 groups and found that psychological safety predicted task performance and citizenship behavior beyond engagement and positive leader relationships.

[5] Hao, Leilei, Hui Zhu, Yuqian He, Jinyun Duan, Teng Zhao, and Hui Meng. “When Is Silence Golden? A Meta-Analysis on Antecedents and Outcomes of Employee Silence.” Journal of Business and Psychology 38 (2023): 1025–54. doi:10.1007/s10869-021-09788-7.

• Synthesized 168 samples and 63,134 employees and found that silence was associated with poorer attitudes, task performance, and citizenship behavior, while psychological safety strongly influenced whether employees spoke up.

[6] Martin, Robin, Yves Guillaume, Geoff Thomas, Allan Lee, and Olga Epitropaki. “Leader–Member Exchange and Performance: A Meta-Analytic Review.” Personnel Psychology 69, no. 1 (2016): 67–121. doi:10.1111/peps.12100.

• Synthesized 146 task-performance samples, 97 citizenship samples, and 19 counterproductive-behavior samples and found that stronger manager–employee relationships predicted better performance and behavior, with trust serving as the strongest mediator.

[7] Dulebohn, James H., William H. Bommer, Robert C. Liden, Robyn L. Brouer, and Gerald R. Ferris. “A Meta-Analysis of Antecedents and Consequences of Leader-Member Exchange: Integrating the Past with an Eye toward the Future.” Journal of Management 38, no. 6 (2012): 1715–59. doi:10.1177/0149206311415280.

• Synthesized 247 studies and 290 samples and found that leader behaviors and perceptions explained more variation in manager–employee relationship quality than follower or contextual factors.

[8] Eisenberger, Robert, Florence Stinglhamber, Christian Vandenberghe, Ivan L. Sucharski, and Linda Rhoades. “Perceived Supervisor Support: Contributions to Perceived Organizational Support and Employee Retention.” Journal of Applied Psychology 87, no. 3 (2002): 565–73. doi:10.1037/0021-9010.87.3.565.

• Studied 314, 300, and 493 employees across three field studies and found that supervisor support increased employees’ sense that the organization valued them and was associated with lower turnover.

[9] Liu, Shengmin, and Zhenyu Ling. “How Does Authoritarian Leadership and Abusive Supervision Suppress Employee Voice? A Meta-Analysis Based on Cognitive and Resource Perspectives.” Baltic Journal of Management 20 (2025): 248–65. doi:10.1108/BJM-10-2024-0622.

• Synthesized 354 articles, 427 effects, and 169,127 participants and found that authoritarian and abusive leadership suppressed employee voice partly by damaging psychological safety and manager–employee relationships.

[10] Allen, Joseph A., Nale Lehmann-Willenbrock, and Nicole Landowski. “Linking Pre-Meeting Communication to Meeting Effectiveness.” Journal of Managerial Psychology 29, no. 8 (2014): 1064–81. doi:10.1108/JMP-09-2012-0265.

• Surveyed 252 working adults and found that pre-meeting small talk predicted perceived meeting effectiveness beyond the contribution of effective meeting procedures.

[11] Luong, Alexandra, and Steven G. Rogelberg. “Meetings and More Meetings: The Relationship between Meeting Load and the Daily Well-Being of Employees.” Group Dynamics: Theory, Research, and Practice 9, no. 1 (2005): 58–67. doi:10.1037/1089-2699.9.1.58.

• Tracked employees for five workdays in a daily-diary study and found that attending more meetings predicted greater daily fatigue and subjective workload; the participant total was not reported in the available abstract.

[12] Scott, Kim. Radical Candor: Be a Kick-Ass Boss Without Losing Your Humanity. Fully revised and updated ed. New York: St. Martin’s Press, 2019.

• Practitioner book with no empirical sample that presents the “Care Personally, Challenge Directly” framework and recommends weekly 1:1s as a recurring space for candor, feedback, and relationship maintenance.

[13] Hosseinkashi, Yasaman, Lev Tankelevitch, Jamie Pool, Ross Cutler, and Chinmaya Madan. “Meeting Effectiveness and Inclusiveness: Large-Scale Measurement, Identification of Key Features, and Prediction in Real-World Remote Meetings.” Proceedings of the ACM on Human-Computer Interaction 8, CSCW1 (2024): article 93, 1–39. doi:10.1145/3637370.

• Analyzed 7,417 meeting survey responses across five organizations and found that participation strongly predicted inclusiveness and effectiveness, while calendar and telemetry data could not fully capture participants’ experiences.

[14] Allen, Joseph A., Nale Lehmann-Willenbrock, and Stephanie J. Sands. “Meetings as a Positive Boost? How and When Meeting Satisfaction Impacts Employee Empowerment.” Journal of Business Research 69, no. 10 (2016): 4340–47. doi:10.1016/j.jbusres.2016.04.011.

• Surveyed 248 working adults and retained 148 at follow-up, finding that meeting satisfaction predicted later psychological empowerment partly by improving information availability.

[15] Kluger, Avraham N., and Angelo DeNisi. “The Effects of Feedback Interventions on Performance: A Historical Review, a Meta-Analysis, and a Preliminary Feedback Intervention Theory.” Psychological Bulletin 119, no. 2 (1996): 254–84. doi:10.1037/0033-2909.119.2.254.

• Synthesized 607 effects and 23,663 observations and found that feedback improved performance on average but reduced it in more than one-third of cases, especially when attention shifted from the task toward the recipient’s identity.

[16] Gnepp, Jackie, Joshua Klayman, Ian O. Williamson, and Sema Barlas. “The Future of Feedback: Motivating Performance Improvement through Future-Focused Feedback.” PLOS ONE 15, no. 6 (2020): e0234444. doi:10.1371/journal.pone.0234444.

• Studied 924 managers, executives, and MBA students across three studies and found that future-focused feedback better predicted acceptance and intentions to improve than arguments over past performance.

[17] Zyberaj, Jetmir. “Examining the Relationship between Supervisory Feedback Characteristics and Employee Feedback Processing: A Systematic Review and Meta-Analysis.” Current Psychology (2026). doi:10.1007/s12144-026-09323-y.

• Synthesized 24 studies and 595,950 participants and found that feedback credibility, quality, supportiveness, valence, and source characteristics influenced whether employees perceived, accepted, and used feedback.

[18] Anseel, Frederik, Adam S. Beatty, Winny Shen, Filip Lievens, and Paul R. Sackett. “How Are We Doing after 30 Years? A Meta-Analytic Review of the Antecedents and Outcomes of Feedback-Seeking Behavior.” Journal of Management 41, no. 1 (2015): 318–48. doi:10.1177/0149206313484521.

• Meta-analyzed thirty years of feedback-seeking research and found that transformational leadership and high-quality relationships encouraged feedback seeking, while its average relationship with performance was small.

[19] Nicolau, Andreea, Octav Sorin Candel, Ticu Constantin, and Ad Kleingeld. “The Effects of Executive Coaching on Behaviors, Attitudes, and Personal Characteristics: A Meta-Analysis of Randomized Control Trial Studies.” Frontiers in Psychology 14 (2023): 1089797. doi:10.3389/fpsyg.2023.1089797.

• Synthesized 20 randomized studies and found that executive coaching produced positive effects, particularly on behavior, while the number of sessions did not significantly predict outcomes.

[20] Cannon-Bowers, Janis A., Clint A. Bowers, Catherine E. Carlson, Shannon L. Doherty, Jocelyne Evans, and Julie Hall. “Workplace Coaching: A Meta-Analysis and Recommendations for Advancing the Science of Coaching.” Frontiers in Psychology 14 (2023): 1204166. doi:10.3389/fpsyg.2023.1204166.

• Synthesized 11 workplace-coaching studies and found a moderate positive effect, with no clear advantage for face-to-face delivery or for accumulating more sessions or coaching hours.

[21] Lloyd, Karina J., Diana Boer, Joshua W. Keller, and Sven Voelpel. “Is My Boss Really Listening to Me? The Impact of Perceived Supervisor Listening on Emotional Exhaustion, Turnover Intention, and Organizational Citizenship Behavior.” Journal of Business Ethics 130, no. 3 (2015): 509–24. doi:10.1007/s10551-014-2242-4.

• Studied 43 employees working under 18 managers and a second sample of 328 employees and found that perceived supervisor listening predicted less exhaustion and turnover intention and more voluntary helpful behavior.

[22] Borut, Limor, Avraham N. Kluger, Harry T. Reis, and Debra L. Shapiro. “How, If at All, Do Perceptions of Supervisor’s Listening Differ from General Relationship Quality? Psychometric Analysis.” Journal of Business and Psychology 40 (2025): 285–314. doi:10.1007/s10869-024-09938-7.

• Surveyed 2,038 subordinates and found that perceived supervisor listening overlapped heavily with trust, humility, support, rudeness, and the broader quality of the manager–employee relationship.

Outside the System

I write for individuals who are tired of inherited scripts, who want to build a life they don't need to escape from.

By Annabelle Botea

Annabelle Botea studied political science and law at Sciences Po, advised in the Romanian Parliament, and worked global health policy for an NGO at the UN level. On paper, it looked perfect. Underneath it, she was running on four coffees a day and popping medicine like candy just to keep going. Then burnout forced the stop she couldn’t give herself.

In this conversation, Dan and Annabelle get into:

• The exact moment burnout stopped being abstract and became physical

• Why she treats intuition and emotional intelligence as a competitive advantage, not a soft skill

• “Brenda”: the name she gave her inner critic, and how she sends her for a walk

• Why she doesn’t allow “party poopers” in her Substack comments, and the boundary behind that rule

• Building Pitaya and rejecting the “10k a month in three months” myth of online business

• What she wants to give future employees that she never had: emotional safety

Annabelle now writes Outside the System on Substack and is building Pitaya, helping first-time founders simplify selling digital products and services online.

If you’ve ever mistaken burnout for a personality trait, this one’s for you.

Like the show? Learn something? Consider subscribing to commit your support.

Subscribe now

Giulia Scalaberni started as a developer, moved into data analysis, then became product manager and team lead on the same platform she used to code. Now she runs a fully remote team of almost twenty people spread across Europe and India, and she’s spent the last several years building out something she calls “humanship” — leadership that treats empathy and high standards as the same skill, not opposing ones.

Some of what we get into:

• Why her team went completely silent for a week after she asked “any questions?” during onboarding, and the low-effort workshop that fixed it (three questions, zero work talk allowed).

• Erin Meyer’s Culture Map, and what it actually means to build trust with people who won’t just tell you something’s unclear.

• “Everything urgent, nothing urgent really” — her rule for slowing down decisions that don’t actually need to move today.

• The meeting where she was the youngest person in the room, asked to speak last, and said out loud that she had nothing left to add. Why she now wants more people on her team to feel safe doing exactly that.

• Ikigai, a bus driver, and why she thinks purpose doesn’t require your job title to sound impressive.

• Her advice for senior leaders comes down to one line: if your dishwasher can’t make it in, your whole restaurant has a bad night. That’s basically the episode title now.

Giulia writes about all of this on her Substack, Humanship. Link’s below, along with her LinkedIn.

https://www.linkedin.com/in/giulia-scalaberni-665175124/

https://substack.com/@giuliascalaberni

Humanship

Your reminder to lead with kindness, true engagement and cross-cultural awareness

By Giulia Scalaberni

Brandi Copeland has spent her career learning that employee experience isn’t the splashy stuff, welcome gifts, offsites, culture decks. It’s the boring, granular work: clear handoffs, the right email at the right moment, a manager who tells you why instead of leaving you guessing.

Brandi calls herself an “accidental HR professional.” She came up through accounting and finance at MetLife and Disney before falling into recruiting, then went on to build Disney’s cast member rotation program and lead talent experience at NBCUniversal. Now she runs The Employee Experience Edit, helping companies fix what’s actually broken instead of throwing perks at the problem.

In this conversation:

• Why “employee experience” has nothing to do with welcome gifts and everything to do with whether someone’s intranet actually answers their question

• The uncomfortable math behind disengagement: direct-report loads are up roughly 50% over the last decade while L&D investment keeps shrinking

• A generational breakdown that reframes Gen Z’s “distrust everything” reputation as the loudest voice for the changes millennials were too gun-shy to ask for

• Brandi’s simple framework for emotionally intelligent feedback, expectation, impact, result, then get curious instead of leading the witness

• Why the fix for most workplace problems is free: “Talking to your people is free.”

Career advice for every level closes it out, from first-day-ever advice, to the messy middle managing up and down, to what CEOs get wrong when they outsource the employee experience entirely.

Brandi also writes a great Substack of her own, link below if you want more of her thinking on this.

Brandi Substack --> https://substack.com/@employeeexperienceedit

Being a workplace chameleon isn’t fake — it’s one of the clearest signs of high emotional intelligence.

HR tech leader Claire joins Dan Korus to unpack what actually separates people with real EQ from everyone else: not “reading the room,” but knowing yourself well enough to change how you show up without losing who you are. Claire’s spent five years across recruiting, employee relations, and onboarding before landing in HR automation — and she brings the rare perspective of someone who’s automated the busywork and still had to sit across the table from burned-out teams.

In this episode:

• Why adapting your communication style for sales vs. engineering isn’t disingenuous — “it’s still you, just a chameleon”

• The real definition of burnout: not caring too much, but losing control over your ability to recover

• Claire’s framework for finding your “So What” — the personal philosophy that turns a job into meaningful work

• Why AI is raising the bar for mediocre output instead of replacing human judgment

• Career advice for first-day hires, messy-middle managers, and CEOs at 10,000 feet: “the folks closest to the issue have the best potential solutions”

If you’ve ever been told you’re “too intense,” or wondered whether adapting to different people makes you a fraud, this one’s for you.

#EmotionalIntelligence #HRTech #Leadership #Burnout #WorkplaceCulture #FutureOfWork #PeopleFirst #CareerAdvice #SelfAwareness #AIatWork #KestrylEdge #HRLeadership #WorkplaceWellbeing

Learn more about Kestryl Edge: kestryledge.com

In researching Jennifer, not far at all.

She’s a systems optimizing leader who designs and forges workplaces that are built for the people.

To her name are several decades of work in HR, leadership, governance, and organizational design.

She’s a leader not for the money, fame, glory, but because she can make a positive difference.

For the love of the game.

For those who sit in their job, defeated, a little frustrated, thinking, “There has to be a better way than this?”

Jennifer Houle can show you that way.

Jennifer knows her shit and puts people first.

Who are you today?

2026 has been one of the most challenging years of my life. Usually when people say that, they're speaking from the other side of the transformation, so they've made sense of it, and they can tell you what’s changed, but I'm still very much in the middle of it. I guess that’s who I am today, someone who’s in the thick of it, but hopeful about what’s on the other side.

Tell us your story of how you got here.

If we’re speaking career-wise, then I got here via three things: luck, hustle, and ADHD.

Luck, because there have been people throughout my life who saw something in me before I saw it in myself. They nudged me toward opportunities I never would have pursued on my own.

Hustle, because once I step through an open door, I work relentlessly to make sure I deserve to be there. If I’m going to do something, I want to become exceptional at it.

I wasn’t diagnosed with ADHD until my forties, but looking back, it explains a lot. The systems I built to compensate became strengths, and my curiosity became an asset. My ability to see patterns and think nonlinearly has become the foundation of my career.

What did you do in order to grow?

I don’t have a post-secondary degree. In fact, I barely graduated high school, and for a long time, I was embarrassed by that. Traditional education, the structure of it all, the curriculum, even the physical space of the institution itself has always felt uncomfortable for me. I now understand that experience through the lens of neurodivergence, but at the time it just felt like I was really stupid. I would see some people I knew breeze through university and think, really? I’m dumber than that guy??

Eventually, I realized that maybe the conventional education system isn’t built for everyone. Once I stopped seeing that as a reflection of my intelligence, I found another way. I challenged the professional designation exam for Human Resources and earned the same designation as people who had taken the traditional route. I just got there on my own terms.

Then, I just never stopped learning. I read constantly. I ask too many questions. I push myself into situations that stretch me.

For years I assumed I must be terrified of public speaking because everyone says they are. Then, one day I decided I wanted to be a speaker, so I pitched to an event called DisruptHR, and was accepted. Then I did it again two years later.

I realized I wasn’t actually afraid to do it; I had just accepted someone else’s narrative as my own. For the last two years, I’ve been a speaker coach for the event.

The same thing happened with writing. I always felt like I wasn’t qualified to write about HR without a degree, even though I’ve been in the field for over 15 years. But writing is my passion, so I went for it. Once I started betting on myself, opportunities began finding me. I’ve been featured and interviewed multiple times as an HR expert in The Globe and Mail, published in HR magazines, and was personally invited by my profession’s regulatory body to deliver a webinar for HR professionals.

If I want to grow, then I must refuse to accept constructed limitations until I’ve tested whether they’re actually true.

How did you learn emotional intelligence?

My understanding of emotional intelligence was shaped by being an observant person. I will always question why people behave the way they do. Especially in my line of work, you will see people at their absolute worst. I mean, people will behave outrageously. But it’s so reductive to say, “Wow, what’s wrong with that person?” Instead, there’s more value in asking something like, “What factors are at play that are making this person behave this way?”

Once you realize that not everyone makes space for those observations, for that grace, you attach a name to it. Maybe it’s emotional intelligence? Whatever it is, I believe it’s a practice…a muscle that needs building and then constantly requires exercise, because without that, it atrophies, and I don’t ever want that to happen to me.

How would you change the workplace if you could change anything?

I‘d stop the powers that be from intervening at the symptom level and start reflecting on the system. By that I mean stop treating every problem as though it’s tied to individuals. Have you ever worked at a company where they’re always getting rid of “problem people”, yet, somehow, the same issues keep popping up even though the players have changed? That’s a systemic issue, not a people one.

That’s the foundation of the work I’m doing through Uncompliant. I want to help people become more intentional about designing the human systems that shape how work is actually experienced. We invest enormous effort into designing products, services, and customer experiences. We need to apply that same level of intention to the experience of work itself.

What is leadership to you?

It's easier for me to explain what leadership isn't because I think that tells you much more about what I believe leadership is. To me, the opposite of leadership is protecting your own comfort, status, or ego at the expense of the people and systems you're responsible for.

When do you feel you became a leader?

I hesitate to call myself a leader because I associate that word with hierarchy, and I’m not into that. But just because you hesitate to define yourself as a leader doesn’t mean other people don’t see you as one.

Once I started putting my ideas into the world through my writing, people...strangers, started reaching out to tell me things like, “You said what I’ve been feeling for years,” or, “You put words to something I couldn’t explain.” I’m not trying to lead anyone or anything, but I’ve come to realize that when you’re willing to say something out loud where others might hesitate, then you give them permission to do the same. Maybe that’s leadership.

Did you change after becoming a leader? If so, how?

I grew a tail…it’s a bit of an issue.

I will always pursue personal growth and transformation, so yes. Leadership is just a byproduct.

What’s a funny, ridiculous, embarrassing, or wild story from your life?

One day, I was out grocery shopping, and every time I went down an aisle, I ran into the same elderly man. Because it kept happening, we eventually started acknowledging each other. First, with a nod and a smile, then with an “Oh, hi again,” and a friendly laugh. It was funny! We had built this little friendship.

After grocery shopping, I had to run to the pharmacy next door. I walked in, and who do I see but my elderly friend, reaching for some items on a shelf. So, since we were now besties, I walked up behind him and whispered, “I’m following you.” But when he slowly turned around to face me, I realized this wasn’t the same man from the grocery store.

I saw the terror spread across this poor man’s face, and instead of apologizing or explaining myself, I panicked and fled the pharmacy.

My friends and family still use this incident to terrorize me, even though it was years ago. They will randomly whisper, “I’m following you,” or ask me if I’ve threatened any seniors lately.

What emotions do you read from people? What do you do about it?

It’s not so much a “read” for me as it is a sensation. I think those who know, know. But for those who don’t, I’ll try to explain it.

If someone is feeling sad, I am sad for them, of course, and if they’re happy, I’m happy for them. But I also feel disrupted, as though my energy has been displaced. Have you ever seen those slowed-down videos of someone sneezing, where you can see how far and wide their sneeze juices spread? That’s what it feels like to be around people who are in a heightened emotional state. They’re getting their emotional sneeze juices on me, and I can see it and feel it, and now it’s on me, and now I’ve breathed it in.

As a result, I have a very short social battery. To cope with that, I need to take frequent breaks in social situations. I’m very selective about how I spend my time and with whom I spend it.

How does power affect you?

It depends. If power is being weaponized, then I find it deeply uncomfortable. If it's being used to challenge ideas, create opportunities, or improve systems, then I’m okay with it. It really comes down to whether power is being used to serve the person holding it or the people impacted by it.

What decision looked reasonable at the time but troubles you now?

Having a kid!

I’m not troubled by how hard or exhausting it is to parent; my dog is more exhausting than my son. But the moment I became a mother, I discovered a depth of vulnerability I didn’t know existed. That’s troubling. The lack of control is troubling.

That said, in every lifetime, I hope to experience the joy of knowing him.

What feedback has followed you through more than one job or chapter of your life? Why has it been difficult to change?

My strongest feedback loop is a behavior I’ve repeatedly observed in myself.

My mom has a very domineering personality, and I learned early on that accommodating her was easier than challenging her. I brought that pattern into adulthood, finding myself gravitating toward friendships and relationships where I was easily dominated.

I’m aware of it; I’ve made a lot of positive changes, but it’s still there, and in vulnerable moments, it comes out. Some of that has shown up in my work, too. There have been times when I have absolutely prioritized harmony over speaking up. I’m getting much better at recognizing those moments, but it’s a practice.

Jennifer is big on polls.

What do you wish you learned earlier?

I wish I’d learned to love and respect myself way sooner in life.

I mean this very practically: You can have the most supportive family, friends, and community, but at the end of the day, you’ve really only got yourself. And if you don’t genuinely love and respect yourself, then you actually have nothing. How bleak does that sound?

A huge part of learning to love yourself is believing you deserve a full life. Why shouldn’t I be the one to write the book, give the keynote, or build something meaningful? For the first time in my life, I’m starting to believe that I can actually do those things, and it’s only because I respect myself enough to try.

What’s an underrated skill to develop as a leader? How would you coach someone to learn it?

I don't think we spend nearly enough time teaching leaders how to slow down. Most leadership development focuses on what to say, how to influence outcomes, how to delegate, but I believe active observation is where strong leadership begins. Before you can solve any problem, you have to see it clearly. I'd coach someone to spend less time trying to move fast and more time becoming curious. Curiosity almost always produces better leadership outcomes than certainty.

What’s a hill you will die on without regrets?

We’ve built a world where work has become the organizing principle of human life.

We measure our worth by our productivity, job titles, and how busy we are. What an absolute tragedy. Don’t get me wrong…purpose and contribution matter. But work should enrich life, not consume it.

My son’s classroom has a wall with pictures of what the kids want to be when they grow up. Another parent was shaking their head at how many kids said “YouTuber,” but I have a different perspective. Without even realizing it, these kids are questioning assumptions my generation just accepted. Can work be creative, flexible, joyful, and integrated into life instead of dominating it? I hope the answer is yes.

Who do you look up to? Why them?

I don’t know that I look up to anyone in particular, but I genuinely and profoundly love women so much. We instinctively understand what we’ve had to overcome just to get where we are; hell, sometimes just to exist. There’s an unspoken kinship that comes from having navigated this world as women, and no one can take that away from us.

My sister, my niece, my friends, women in my community. And on Substack? Just to name a few…Rebecca from the Strategic Linguist. JHong from Natural Intelligence. Kathi from Chief Absurdist Officer. Shannon from The Flow. Brandi from The Corporate Unspiral. Amanda from Saved Not Sent. Rose from She’s Scrappy. Candy from Joint Custody. Megs from Pizza and Other Things. Chiedza from The Investigative Edge. Tricia from The Cunningly Good Marketer. from Workmanshit. Have you seen the work these women are doing? It’s so diverse, so brilliant. I’m in awe.

What advice do you have for someone starting their first day of work?

Pay attention, because every organization has an informal network more powerful than the formal hierarchy. You got the job; you’ve already impressed them. Now you need to understand the system you've just joined. People who understand the system adapt faster, build stronger relationships, and are more effective because they work with the system instead of unknowingly working against it.

What advice do you have for the messy middle? The middle managers, the team leads, the senior contributors?

The system is designed so that middle managers spend the bulk of their time absorbing pressure from above and shielding everyone below. It feels noble, but it’s unsustainable, and it hides problems the organization actually needs to see.

My advice is to become a sense-maker instead. Translate strategy into something people can act on, and translate the lived experience of your team back to leadership in a way that helps them make better decisions. It’s not your job to protect the organization from broken systems, but it is your responsibility to help make them visible.

What advice do you have for senior leaders? The rain makers, the C-Suite, the people at the top?

Get off the damn balcony every once in a while! The more senior you become, the more time you’ll spend there, because that’s the job, and it’s important. But if strategy happens on the balcony, the consequences of your decisions are experienced on the dance floor.

You want to be strategic? Remember that your title changes your vantage point, but it doesn’t change reality. Make a habit of returning to the places where your work is felt. See how your decisions show up in meetings, processes, customer interactions, and the everyday experience of work. Listen with curiosity, not defensiveness.

From others, we learn. Deeper roots, flying higher.

If you’re not already subscribed, consider doing so, or following, in order to stay involved in The Updraft.

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More from Jennifer

Uncompliant

A publication about modern work that examines inherited systems, questions what we've normalized, and explores what healthier, more effective organizations could become.

By Jennifer Houle

Roast the Post Podcast

Roast the Post helps job seekers dodge bad roles and helps employers stop publishing them, one brutally honest episode at a time.

By Paul Austin-Menear

Uncompliant

Your Next Hire Should Make You Uncomfortable

A few weeks ago, I wrote about the outdated origins of the interview process. You know, the frameworks designed in the early 1900s by a handful of men with narrow, exclusionary views of what made someone a “good worker…

Read more

a year ago · 26 likes · 23 comments · Jennifer Houle

The Updraft is a publication for writing on leadership and emotional intelligence.

I’m Dan Korus. Writer, runner, lover of milk duds, fully caught up on One Piece, dog walker, and founder of Kestryl Edge: a company dedicated to bringing emotional intelligence skills to leaders in the workplace.

Weekly essays, podcasts, lives, and interviews all on striving towards being a better leader.

Tomorrow morning, Crosswinds episode one will be published. This is a written interview of a leader who has graciously accepted the invitation.

Anemomorphogenesis

Trees grown in tunnels, biospheres, and indoors grow differently than those grown outdoors. They often die.

Stagnent air creates high-moisture environments leading to root rot and fungal decay.

Gases linger and choke the trees from the fresh air required for photosynthesis and respiration.

Chiefly, there’s no wind.

Swaying in the breeze triggers a signal in trees to grow thicker wood and deeper roots.

Without the wind trees grow to collapse under their own weight.

Resistance is vital to building strength.

On buying time

The things money can’t buy funnily enough end up being the most valuable in life. A belly laugh or a hug with a close friend.

Rue the day when we can buy time directly with money.

Though, we can save the time we have left by learning from others.

Touch the stove yourself, or listen to the person who got burnt first.

Others can distill decades of trial, effort, and success into a few short sentences.

Why burn your own hand when you could listen instead?

Why search blindly when you could use a treasure map?

To grow

Crosswinds is meant to fill our cups. I’ve heard many interviews about people’s successes, their triumphs, and their ascensions into corporate glory.

And I learn nothing from those interviews.

Boring! Banal and archatypal of the lies we spin about the self-made CEO. No rough edges.

Crosswinds aims to scavenge, collect, and share leadership knowledge. There’s a focus on emotional intelligence and on the journey.

Through this we can cross examine ourselves.

Our skin harder, roots deeper, flying higher, and time on our side. Even if just a little.

Up first, Jennifer Houle

Jennifer’s interview publishes tomorrow. She writes “for people who believe better workplaces begin with better thinking.”

She believe in scrutinizing structure before pointing a finger at people and that understanding the systems is the first step to improving culture, equity, and the invisible currents of power flowing in the workplace.

She’s spent decades in HR, leadership and the spaces in-between. Currently, Jennifer is rocking it as an HR executive at a North American VC firm.

Jennifer writes Uncompliant and is a contributor in the written HR and executive spaces, she delivers talks and workshops, and she co-hosts Roast the Post. Roast the Post is podcast that reviews current job postings. It’s worth the listen.

She also serves on different boards and various organizations as a leader.

If it’s not obvious already, Jennifer is someone who cares. She pours herself into the communities around her not because she expects anything back, but because she’s good at it and she wants systems to serve people.

Jennifer knows there is a better way. She’s a leader who works hard to bring us that much closer.

Her interview is wonderful. Raw, honest, and very funny. Keep an eye out for it and be ready to sit back with a warm drink, a notebook, and a few minutes to take a breath and learn from Jennifer Houle.

Not subscribed? For shame! How will you stay in the loop on all this free value delivered right to your inbox? Let’s fix this right here right now.

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Here’s a few nuggets I’ve learned from this episode:

1. Jen is incredibly kind and present, intelligent on many fronts - AI, marketing, the evolution and state of business in America, why communities should own the platforms they love - she knows her stuff, and,…, overall is someone who you would be blessed to have in your network.

   If you are a subscriber of The Updraft I HIGHLY recommend checking out .

2. AI changes many things and in some ways changes nothing, it shouldn’t be called AI, and how we engage with AI should be similar to how we vote, chose products, and enter legal agreements… AI is occurring and developing with or without us. Through our involvement, we can help shape its future to be something that serves us.

3. Curation of a personal brand happens in the same way. Our choice becomes how we harness and nurture that brand over time.

If my nugget left you with questions, yep. Me too. Folks like Jen are here to cut through the noise and put to bed harmful folklore and mythos that muddy the current AI landscape.

Natural Intelligence X The Updraft

Curious about how AI changes the concentration of work in our day to day?

About the degrees we were told to get and AI’s impact on the future job economy?

Pondering the BoF x McKinsey State of Fashion 2026 report and what it means for you?

Natural Intelligence

Hidden Figures: The Work That Was Always Load-Bearing

Hi. I’m Dan Korus…

Read more

16 days ago · 37 likes · 38 comments · JHong and Dan Korus

What are my favorite birds?

How do I use AI when I own an emotional intelligence company?

Why I take screenshots of AI written notes that use the word ‘Clarity.’

Natural Intelligence

The Natural Intelligence 2.0 - Dan Korus

The most interesting insights about artificial intelligence come from natural intelligence. New questions, new voices. Welcome to NI20 2.0. This week: Dan Korus…

Read more

13 days ago · 29 likes · 17 comments · JHong and Dan Korus

About The Episode

Is AI actually intelligent, or just a very good mirror of us? Jennifer Hong, fractional CMO and writer behind the Substack Natural Intelligence, joins Dan Korus for a conversation that moves fast: why image generators keep failing to render real human faces (she calls it “the centroid problem”), why she switched from OpenAI to Anthropic and compares the two to Tesla and Volvo, and why she picked a public fight with Substack’s leadership over its handling of death threats and deepfakes on the platform.

They also get into:

• Why “AI fluent” describes less than 1% of users, and what that number actually means

• The 95/10 to 15 self-awareness gap and what it means for leaders specifically

• The difference between a jerk and an asshole at work, and why only one is a dealbreaker

• How two life crises rebuilt Jennifer’s relationship with control, trust, and delegation

• Why personal branding is a prenup you’re already signing whether you write it down or not

• The plan to buy back Letterboxd for its community instead of selling to private equity

A conversation about self-awareness, trust, and what’s left for humans once machines get good at mimicking the average.

Timestamps
0:00 Intro
0:38 Does “intelligence is no longer ours alone” still hold a year later
2:53 If not intelligence, what would you call it: the “centroid” problem
9:47 Why she switched from OpenAI to Anthropic: Tesla vs. Volvo
13:57 Growing up in Los Altos, getting kicked out of Berkeley
20:37 The rules she breaks: buying back Letterboxd from private equity
25:12 Substack’s Nazi problem, the open letter, and getting threatened for it
29:38 “Low-key Buddhism” and letting go of control
35:05 Trust and delegation as a leader
36:09 The health crisis that became her line of demarcation
48:31 Personal branding is a prenup you’re already signing
58:12 The 95/10-15 self-awareness gap and EQ diagnostics
1:03:39 Lightning round: good leadership, first-day advice, advice for execs
1:15:09 Where to find Jennifer Hong

Follow Jennifer Hong
Substack (Natural Intelligence): hongjennifer.substack.com

Natural Intelligence

How to human in the age of AI - with curiosity, random musings, critical rigor, and a low-key Buddhist shrug.

By JHong

JHong’s LinkedIn: https://www.linkedin.com/in/jennifer-hong-100/

More from Kestryl Edge
Website: www.kestryledge.com
The Updraft (Substack): dankorus.substack.com

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Hashtags
#EmotionalIntelligence #Leadership #ArtificialIntelligence #SelfAwareness #Substack #PsychologicalSafety #PersonalBranding #AIEthics #Podcast #KestrylEdge

The more power, status, and cultural familiarity you have, the more of your “true self” you can bring to work without paying for it. Everyone else learns to codeswitch, mask, and edit. We change the clothes, conceal the history, and calculate which version of ourselves the boardroom is prepared to accept.

That does not make authenticity useless. It makes it conditional.

My argument is not that leaders should be fake. It is that “be yourself” is an incomplete and sometimes dangerous leadership prescription.

Leaders owe people honesty, consistency, fairness, and accountability.

Leaders do not owe people an unfiltered performance of the self.

The Lore

Authentic Leadership is a relationship-focused approach centered on genuine, ethical behavior, self-awareness, and transparency, rather than just authority or hierarchy.

The dominant model defines authentic leadership through four dimensions: self-awareness, relational transparency, balanced processing of information, and an internalized moral perspective.1

If you’re curious about Authentic Leadership in a broader context, the full history and evolution of leadership theory and how it stitches into the conceptual fabric, see my further reading list below and check out the annotated references section. If you don’t want to miss out again, the button below is for you. <3

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Meta-analytic evidence associates perceived authentic leadership with favorable follower attitudes, leader outcomes, and performance-related outcomes:2

• Authentic leaders make ethical decisions, have high psychological well-being, and show role modeling positive behaviors.

• Followers feel empowered, identify with their leader, and report higher job performance, satisfaction, trust, and engagement.

• Organizations are associated with stronger ethical climates, greater psychological safety, and, in some studies, improved financial performance.

Much of the evidence relies on followers rating both the leader’s authenticity and the quality of their own work experience. That makes it difficult to separate leadership behavior from follower approval, organizational climate, and halo effects. 3

Leadership books and keynote speakers have increasingly encouraged leaders to communicate purpose, values, and personal conviction as a means of inspiring trust and commitment.4

Generally, authenticity is ingrained in what we think of as a proper modern leader.

In Whither Authentic Leadership?, Jon Billsberry examined 45 empirical studies published in 2024 and 2025, finding that the field often continued its established methodological habits despite major critiques. 5

His review crystallized a concern I've been wrestling with.

The “True Self” Privilege

Authentic Leadership encourages leaders to cultivate self-awareness, transparency, and alignment with what it describes as their "true self."6

The framework encourages leaders to identify their values and bring them into their professional relationships.

The language surrounding authentic leadership often carries an implicit moral hierarchy. We begin describing authentic leaders not only as more trustworthy, but as better people. The implication is subtle but powerful: authenticity becomes evidence of moral superiority.

For anyone who isn’t the typical white, cisgender male leader, being “real” can cost you credibility. A study of LGBTQ leaders showed how corporate expectations to be “authentic” was often exhausting, invasive, and coercive.7

Typical leaders are more likely to have their mannerisms read as natural leadership. Atypical leaders are more likely to have the same mannerisms inspected as identity, politics, aggression, weakness, or deviation.

Atypical leaders often end up feeling pressured to wear a costume. 8

Employees sometimes create “facades of conformity,” concealing personal values or identities to appear aligned with the organization. Minority status and nonparticipative work environments can increase that pressure.9

You perform “leader” in a way that reads as acceptable.

You’re allowed to be vulnerable, but only if it doesn’t make you seem weak.

Instead of liberating the self, “authenticity” can become another form of corporate control, binding people even tighter to the emotional labor demands of fitting the mold. 10

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Authenticity as a Label, Not a Trait

One suggestion is to look at authenticity as a follower label put onto the leader, not a style a leader can embody through personal decision. 11

Think about it this way: if someone says, “I’m cool,” that instantly makes them uncool.
Coolness is a trait decided by the onlooker; authenticity is in the eye of the beholder.

When a follower describes a leader as authentic, they are expressing comfort, trust, and alignment. A lack of authenticity is related to feelings of betrayal or unmet expectations. Authentic leadership is therefore not a style per se, but a cultural idiom followers use to judge moral legitimacy.

In this way, the leader’s role becomes surprisingly modest.

You cannot declare yourself authentic any more than you can declare yourself funny, trustworthy, or charismatic. Those are judgments other people make after watching your behavior over time.

Your responsibility is simply to act with consistency, explain your intent, tell the truth about difficult decisions, and align your actions with your stated values. Whether others experience that as authenticity is ultimately their decision.

Supporting atypical leaders, then, becomes less about encouraging everyone to “be themselves” and more about examining the filters through which we evaluate people. We should ask whether we are rewarding integrity or merely rewarding familiarity. Are we calling someone authentic because they are principled, or because they happen to look, sound, and behave like the leaders we have always expected?

“I’m just direct…”

The academic construct is more disciplined than the corporate slogan it produced. In practice, relational transparency, vulnerability, “bringing your whole self,” and unfiltered candor are routinely mashed into one.

So we confuse authenticity with immediacy.

Social context and status change the name we give behavior. 12

• A powerful person is “direct.”

• A junior employee is “difficult.”

• A man is “assertive.”

• A woman is “emotional.”

• A familiar leader is “authentic.”

• An atypical leader is “political.”

Privilege does not merely permit expression. It helps decide how expression will be translated.

Direct language does not excuse rude behavior.

Your first impulse is not automatically your truest self. Authenticity is not unfiltered transparency.

People still experience regulated emotions as authentic.13

Authenticity is not a free pass excusing the human duty of filtering your own poisonous thoughts before sharing them with others.

You do not control every interpretation of your words. You are still responsible for their foreseeable impact.

Subscribe if someone has ever been a bully to you and justified it with “I’m just direct.”

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Steep Luxury Tax

If I came to work and was my “true self” in any of my past roles, I’d likely have been fired from all of them. I have grown into a very… open and questioning person, and I put on a veil of manners, restraint, patience, and the physical uniform of a corporate professional.

My favorite clothes to wear are cotton shirts washed so many times they are soft and have holes in them along with Carhartt pants. Clothes for relaxing, chopping wood, gardening, cooking, living a life with some dirt in it. The best life.

Yet here I am in my business casual monkey suit so my boss knows I care and so people see me as put together.

Professionalism is a construct. Sometimes it's useful. Sometimes it's exclusionary. Often it's both.

It is not always inclusive or innately diverse, and it’s rarely neutral. It is often a performative ritual.

Is a contextual self necessarily a false self?

A filter is not always dishonesty. Sometimes it is discipline. Sometimes it is respect. Sometimes it is survival.14

The problem is not that everyone adapts. The problem is that some people must adapt far more, while others mistake never having to adapt for moral courage.

Leaders don’t earn trust by being themselves and saying everything they think.

They earn it by making sure what they choose to say consistently reflects who they are trying to become.

That is a far higher bar than simply “being yourself.”

It’s also a more equitable one.

It asks every leader to practice integrity instead of rewarding only those who can safely afford authenticity.

~d

Have you always felt like calls for authenticity were veiled attempts at corporate control? You’re in good company. Share this with other birds of a feather.

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The Updraft

The Updraft is a leadership newsletter meant for aspiring leaders, current leaders, and particularly leaders in high consequence environments. It’s where I get my thoughts on paper and practical tools and reflections to the many while building Kestryl Edge, LLC.

Subscribing guarantees you 1-2 leadership essays each week. I ensure these essays are useful, and I often take input from my audience for future topics.

Further Reading

References

• Be more organized.

• Forget less important shit.

• Have more mental bandwidth for strategic thinking.

• Make better decisions and use time more wisely.

This takes anywhere from 20 minutes to 2 days to set up and can be used for years with no maintenance or adjustment.

Origins

My buddies and I have some wicked group chats. One thing they shared with me that ended up changing my life forever was a systems article on the types of thinking:

1. Survival

2. Reactive

3. Adaptive

4. Strategic

And how each mode was only accessible if you had more time to access those states. A person so busy they are in survival mode doesn’t have time for strategy.

There’s a privilege to not being so busy that you have time to think.

Affording yourself that time comes from implementing systems that reduce cognitive load.

The largest opportunity is usually, in my experience, knowledge management and personal admin.

Read the papers in the References section on how reducing cognitive load is the only way toward strategic thinking.

Hence, the second brain.

Share with the group chat if you need gang to get a grip on their cognitive load.

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Bush Firefighter to Strategy Master

People talk about feeling reactive. Like they are always catching up to something.

This is one of the modes of workflow we all experience.

Reactive work, proactive work, strategic work.

You have to find a way to decrease cognitive load in order to think strategically. 1

For many, this is impossible.

Subscribe if you like It’s Always Sunny in Philadelphia.

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With one piece of software you can start right now. With a Claude pro account this is an agent you can set up in less than an hour. If you have a decent computer, you can run it yourself.

Fear not! There are a few ways you can implement this:

• Free

• Claude Cowork

• Full Local-Machine

I Like Notes. A Lot.

I have an obsession with pens, pencils, writing stationery, notebooks, and paper.

On my list of least favorite sensory experiences is the feeling of a writing utensil scraping against a rough and uneven surface separated by thin, shitty paper.

Make me chew aluminum foil with ants crawling on my back before I subject myself willingly to such an undignified and bullshit writing experience.

On my shelves, you’ll find lab notebooks from my days as a chemist. Experiments and molecular diagrams sketched neatly. Physics calculations and nanoparticle recipes in the margins of tables, data, and observations.

Printed excerpts from articles collaged and annotated as references for new experiment ideas.

You’ll find binders of printed articles. Scribbled on and underlined. Chicken scratch in the margins. Reminders and to-dos as I react and consume the articles, linking the ideas to other things.

There are the journals. Small Moleskines and composition notebooks that held to-do list after to-do list. Idea after idea. Diagram upon diagram.

That’s just the shelves, haha.

My obsession with journals follows me digitally. First to Evernote, then OneNote, then I evolved and found Notion. Then again, finding Obsidian.

The emails, the recorded meeting notes, blogs, blog drafts, code blocks, websites, advertisements, transcripts, CRM information, DMs, texts, articles, and phone calls.

My problem was never that I didn’t like taking notes and hoarding information.

It was that nothing ever came of it.

I’d end up with piles of to-dos and notes and papers and get stressed out and paralyzed by all the information I had that was waiting to be digested and synthesized and acted upon. 2

At one point, I had three digital note software programs, two project management apps, and three physical notebooks.

And none of them overlapped or talked to the others!

Fuckin’ chaos.

My solution?

An autonomous second brain that connects all information inputs in my life, catalogs the information into a singular database, and provides weekly and daily reports on what’s going on and what I need to be focusing on next. 3

The Philosophy of Notes

Sometimes I need to shut the fuck up.

And, pro tip, you can’t talk when you’re writing notes about what’s going on and what someone else is saying.

Taking notes improves active listening.4

It works for me, and it can work for you too.

It improves memory retention. Even if you never look at it again.5

It gives me a place to write down the fleeting ideas.6

I am ADHD-AF. I think new ideas and random thoughts all the time, and if I don’t write them down, they are lost forever.

I also hyper-fixate on emotions and problems. Writing them down helps me feel the feelings, go through the emotional tunnel, and process what’s going on.7

In a paper journal, you’re writing chronologically.

In Obsidian, or Notion, or other linking-capable software, you can tie two ideas together to begin forming a web.

The connection of these ideas and experiences, and the capture of unique notes, is called Zettelkasten.8

The benefits are outstanding but can take time, energy, and discipline in the mundane to see results.

I do a lot. I coach CrossFit, train for ultramarathons, have a full-time job managing a manufacturing team, I’m on the board of directors for a rowing alumni group I founded, and I founded and run a company to deliver training workshops, a weekly podcast, and a biweekly blog. I have a wife I love, two dogs that love to walk, and a cat who follows me around like a shadow.

I have a lot of shit to keep track of.

I cannot do all of it every day.

I am constantly juggling.

My philosophy is threefold:

1. Talk less.

2. Store my information for when I have time to be strategic and analyze it. 9

3. Keep getting the most important things done.

How It Works

I built Peregrine through trial and error. I started out as an agent and over time graduated into constantly running software on my computers.

In brief, the inputs feed the Obsidian vault. Then, my agent combs the new data and updates a few key files, creating and appending files for anything new. The output, aside from the linked files, is a daily email to myself at 4:30 a.m. every morning.

For you, the inputs may vary.

For me, they are the following:

Inputs

iMessage

• Texts about business

• Texts with obligations and dates

• Threads I forgot about

Gmail

• Emails in and out

• Meeting transcripts from Google Meet

Calendar

• Meetings, scheduled, happening, or pushed

• Creating time-sensitive tasks

• Events, generally

• Birthdays

Riverside

• Podcast transcripts

Website

• Visitor analytics

• Workshop sign-ups

Substack

• General analytics

AI Chat History

• Claude

• Gemini

• Ollama

Context Files

Company Context

• Details and dreams for Kestryl Edge

Writing Goals Context

• Previously posted essays

• In-progress drafts

• Writing roadmap

Company Planning Context

• Company roadmap

• Marketing plans

Photos of My Physical Notebooks and Physical Articles

• Anything I wrote in a notebook

• Any schematics I scribbled on paper

• Receipt photos

How the Information Gets Sorted

From there, the information gets sorted into folders in my Obsidian.

People

• Who they are

• Why they matter: friend, client, prospect, network, etc.

• Details: birthday, likes/dislikes, allergies, recommendations, context

• Actions and exchanges: Am I waiting on them for anything, or are they waiting on me?

• Projects and assignments: For people on the Kestryl Team, what are they working on?

• History and research: professional history highlights, any information provided for a podcast guest, for example

• Brief timeline of when we met and the points at which we had interactions: meetings, emails, etc.

Companies

• All people linked to companies

• Tasks related to the companies: proposals, workshops, reports, meetings, etc.

• Who the company is: prospect, customer, client, friend, referral

Groups

• Social groups of friends

• Business groups of peers and colleagues

• Book club

• Dinner groups

Writing

• My drafts

• My published essays

Context

• All my context markdown files I use in my AI adventures.

To-Dos

• Every to-do or action or follow-up. Every. Single. One.

• Conversations for prospects that got dropped

• People who are important and need a re-ping

All of these update files get tweaked, interlinked, and updated from every single day of new information from the input sources. ⁷

The Outputs

Lastly, I get a morning email with the following:

• Summary of the week’s work so far in relation to my weekly/monthly/quarterly goals

• The biggest to-dos on my plate for the day

• The projects I need to push that week

• A list of all my actions sorted by importance, with the easy ones labeled EZPZ

This does a few things for me.

I no longer have to rack my brain for the to-dos and actions of days before. They are all right there. 10

I don’t have to remind myself about following up because the follow-ups are remembered for me. ⁴

I get less distracted with side quests because the main storyline quest lines are right there, neat and tidy. ³

I have an updated to-do list. Every day. I don’t need to write a new one. The thinking is done. ⁷

I can follow my creative urges when I don’t have juice for work, and when I am ready to knock something out, I can tackle what’s at the top of my queue.

When I’m zapped and only have energy for the most transactional tasks? The EZPZ items are right there waiting for me.

My Methods

First of all, I don’t start coding or prompting without a requirements trace.

If I don’t know what the product requirements are, then I’m not building. Simple as that. If you don’t know how to do a systems level requirement trace… we can’t hang out anymore. All my homies trace their requirements. Sorry fam.

Subscribe if you trace your requirements.

Subscribe now

User Need

A personal knowledge management system that reduces cognitive load, captures obligations and ideas across my work and life, organizes them into a trusted source of truth, and sends me a daily operating brief so I can focus on the most important work without constantly trying to remember everything.

System Requirements (full trace below)

Acceptance Criteria

The system is successful if:

1. I receive a useful daily brief every morning.

2. The brief reflects real inputs from the previous day.

3. Follow-ups stop getting lost.

4. Important projects remain visible.

5. I spend less time rebuilding my to-do list from memory.

6. I can trace every major output back to an input source.

7. I can tell when the system is healthy, degraded, or broken.

8. The system reduces cognitive load instead of becoming another cursed productivity altar.

I set this program up using Claude Code and Cursor as a custom application running 24/7 on my Windows machine.

The tool itself calls local models in Ollama for small-context processing, and if Ollama fails, then it runs through my Anthropic or GPT API, depending on the task.

The connections are all monitored with an output in the daily email. The system is queued to do an hourly pull and a health check, and if any of the components fail or return abnormal results, I get a notification with error codes and diagnostics that I can push into Cursor/Claude for resolution. 2

OPSEC

Before anyone starts having a cow about SOC 2, yes, this system touches sensitive information.

Emails. Texts. Calendar invites. Client notes. Business plans. Meeting transcripts.

So I do not treat this like a toy.

The goal is not to shovel my entire life into an AI wood chipper and hope wisdom and ✨clarity✨ comes out the other side. The goal is to build a controlled system that helps me remember, prioritize, and act without spraying private information all over the internet like a busted fire hydrant. ²

A few rules matter.

First, not everything needs AI processing. Some information can be stored, indexed, and retrieved without being digested by a model. Just because an LLM can read something does not mean it should. ¹²

Second, local processing comes first when possible. Small-context tasks run locally through Ollama. If the task can be handled on my machine, it stays on my machine.

Third, external APIs are used intentionally. When something needs a stronger model, it can route through Anthropic or GPT depending on the task, but that is not the default for everything. Sensitive context gets treated differently from generic task sorting. ²

Fourth, I do not want the system making decisions for me. It can summarize, surface, sort, and remind. It does not send emails for me. It does not message clients for me. It does not make commitments for me. It does not pretend to be my judgment. It sorts, compiles, and organizes. ¹²

Fifth, this system needs logs, health checks, and failure alerts. If something breaks, I want to know. If an input stops syncing, I want to know. If a component returns something weird, I want diagnostics. Automation without visibility is just chaos wearing a lab coat. ²

And finally, this is not something I would blindly install inside a company without serious thought around permissions, retention, confidential information, client data, model routing, audit logs, and who gets access to what. ²

For my personal operating system, this is powerful.

For a team or company, this needs governance.

How To: The Three Ways to Build This

You do not need to build the full robot cave version on day one.

Please do not read this and immediately try to superglue together Gmail, Obsidian, OCR, local models, APIs, and a 24/7 Windows daemon with $100 in claude API tokens.

Start simple. Try things out. Do a requirements trace. Then build as you learn what helps you and what is, as GPT would call it, ‘a dumpsterfire wearing corduroy and saying m’lady,’ or whatever.

There are three useful versions of this system:

1. The free manual version

2. The Claude Cowork version

3. The full local-machine version

Pick the one that matches your current level of technical tolerance, and, importantly based on what you’re comfortable debugging.

Option 1: The Free Manual Version

This is the “I do not want to code anything, I do not want to automate anything, I just want my brain to stop leaking” version.

You can build this with Obsidian (or Notion, I think) and 20 minutes.

Step 1: Download Obsidian

Download Obsidian. (sync is $5/month at time of writing and allows your vault to go across all your devices.)

Create a new vault.

Name it something obvious.

Mine would be something like:

Personal Operating System

Usually I go bird themed though. Mine is called Peregrine.

Step 2: Create Your Main Folders

Create these folders:

1. 00 Inbox

2. 01 Daily Notes

3. 02 People

4. 03 Companies

5. 04 Projects

6. 05 To-Dos

7. 06 Writing

8. 07 Context

9. 08 Archive

Step 3: Create One Daily Note Template

Create a note called:

Daily Note Template

Put this in it:

# Daily Note - YYYY-MM-DD

## What happened today?

- 

## New tasks

- [ ] 

## Follow-ups

- [ ] 

## People I interacted with

- 

## Companies or projects mentioned

- 

## Ideas worth keeping

- 

## Decisions made

- 

## What needs my attention tomorrow?

1. 
2. 
3. 

Every day, copy this template into a new daily note.

Name the note by date:

yyyy-mm-dd (or yyyymmdd if you’re a true G)

Step 4: Create a Master To-Do List

Create a note called:

Master To-Do List

Put every open loop in there. (there are plugins you can add that will scrub your notes and compile the to-do’s into a master list.)

Use this format:

# Master To-Do List

## Today

- [ ] 

## This Week

- [ ] 

## Waiting On Someone Else

- [ ] 

## Follow-Ups

- [ ] 

## Someday / Maybe

- [ ] 

If it is not in the system, it does not exist.

Step 5: Create People Notes

Every important person gets a note.

Use this template:

# Person Name

## Who they are

## Why they matter
Friend, client, prospect, teammate, vendor, referral, etc.

## Important details
- Birthday:
- Likes:
- Dislikes:
- Context:
- Personal notes:

## Open loops
- [ ] 

## History
- 

This is where you put the stuff about people.

• Birthday.

• Names of kids.

• Project details.

• Referral context.

• The allergy they mentioned once.

• The thing they care about.

• Their current house remodel or project.

Step 6: Create Company Notes

Every important company gets a note.

Use this template:

# Company Name

## What they are

Prospect, client, partner, referral source, vendor, etc.

## Key people

- [[Person Name]]

## Current status

## Open loops

- [ ] 

## Opportunities

## History
- 

This is especially useful if you sell, consult, manage clients, or run a business.

Which is to say: this is useful if your professional life contains other humans.

Step 7: Create Project Notes

Every project gets a note.

Use this template:

# Project Name

## Desired outcome

## Current status

## Next actions

- [ ] 

## Blockers

## People involved

- [[Person Name]]

## Related companies

- [[Company Name]]

## Notes
[[Related note 1]]
[[related note 2]]

[[Meeting note 1]]
[[meeting note 2]]

## Decisions made
- 

Step 8: Do a 10-Minute Daily Review

At the end of the day, open your daily note and answer:

1. What happened?

2. What did I commit to?

3. Who do I need to follow up with?

4. What did I learn?

5. What are the three most important things for tomorrow?

Then update:

• Your master to-do list

• Any relevant people notes

• Any relevant company notes

• Any relevant project notes

Step 9: Do a 20-Minute Weekly Review

Once per week, open:

• Daily notes from the past week

• Master to-do list

• Active projects

• People notes

• Company notes

Then ask:

1. What did I keep avoiding?

2. What actually matters next week?

3. Who needs a follow-up?

4. What project is secretly dying in a ditch?

5. What can I delete, delegate, or ignore?

Ta-Da!

Other fun options are to import PDFs, meeting notes, important documents, and go through the community plug in pages to see what may be useful.

Option 2: The Claude Cowork Version

This is the middle path.

No local machine daemon. No code. No custom application.

Just Claude, connected sources, a recurring task, and a clear operating prompt.

This is for people who want the system to help them, but do not want to have to code anything, set up APIs, and you maintain access to a chat interface to edit the workflow at any point.

I’ve used this. It’s easy. It works.

Step 1: Create a Claude Project or Workspace for Your Operating System

Create a dedicated Claude space for this.

Call it something obvious:

Personal Operating System

or

Daily Briefing System

or

Star Falcon (birds are sick)

Do not mix this workspace with random chats about recipes, memes, strategy, and racoon memes.

This works best in its own clean workspace.

Step 2: Add Your Core Context

Add a short context document that explains your life and priorities.

Use this:

# Personal Operating Context

## My main roles
- 
- 
- 

## My active projects
- 
- 
- 

## My current goals

### This week
- 

### This month
- 

### This quarter
- 

## Important people
- 

## Important companies or teams
- 

## What I want help with

I want Claude to help me reduce cognitive load by reviewing my recent information, identifying tasks and follow-ups, organizing priorities, and preparing a daily operating brief.

## What Claude should not do

Claude should not send messages, make commitments, schedule meetings, or take action on my behalf unless I explicitly approve it.

In crystallography you can grow other crystals from a seed crystal. This, is a seed crystal.

You can expand upon this but this bare minimum gets you started.

Step 3: Connect the Inputs You Actually Need

Do not connect everything on day one.

That is how you build a haunted productivity aquarium.

Start with the basics:

1. Gmail

2. Google Calendar

3. Google Drive

If you have meeting transcripts in Drive, put them in a folder called:

Meeting Transcripts

(you can have it just scour gmail for it)

If you have business notes, put them in a folder called:

Business Context

If you have writing drafts, put them in:

Writing Drafts

etc., Claude just needs the streams that matter to you.

Step 4: Create Three Simple Source Documents

In Google Drive, create three documents.

Document 1: Active Projects

# Active Projects

## Project Name

### Desired outcome

### Current status

### Next actions

- [ ] 

### Blockers

### People involved
- 

Document 2: Master Action List

# Master Action List

## Today
- [ ] 

## This Week
- [ ] 

## Waiting On Someone Else
- [ ] 

## Follow-Ups
- [ ] 

## Someday / Maybe
- [ ] 

Document 3: Important People and Companies

# Important People and Companies

## People

### Name
- Who they are:
- Why they matter:
- Open loops:
- Notes:

## Companies

### Company Name
- What they are:
- Key people:
- Current status:
- Open loops:
- Notes:

These are your source-of-truth documents. Claude can help update them.

And you can review them, no code required.

Blessed be the simple folder. <3

Step 5: Create the Daily Cowork Task

Create a recurring Claude Cowork task.

Set it to run every morning.

Use this prompt:

Review my connected Gmail, Google Calendar, and relevant Google Drive documents from the last 24 hours.

Use my Personal Operating Context, Active Projects, Master Action List, and Important People and Companies documents as the source of truth.

Create a daily operating brief with the following sections:

1. Top priorities for today
2. New tasks or obligations found
3. Follow-ups I owe
4. People waiting on me
5. People I am waiting on
6. Meetings or deadlines coming up
7. Active projects that need movement
8. Easy transactional tasks labeled EZPZ
9. Anything that looks dropped, stale, or neglected
10. Suggested updates to the Master Action List

Do not send emails.
Do not schedule meetings.
Do not make commitments.
Do not edit source documents unless I explicitly ask.
Surface recommendations only.
Flag anything sensitive or ambiguous instead of acting on it.

This creates the morning briefing.

Not a full second brain, but a very useful and time-saving daily summation! :)

Step 6: Create the Weekly Review Cowork Task

Create another recurring task.

Set it to run once per week.

Use this prompt:

Review the past 7 days of Gmail, Calendar, and relevant Google Drive documents.

Compare what happened this week against my Active Projects, Master Action List, and Personal Operating Context.

Create a weekly review with the following sections:

1. What moved forward
2. What stalled
3. What I avoided
4. Follow-ups that are aging
5. Projects that need attention
6. People I should re-ping
7. Decisions I made this week
8. New opportunities or risks
9. Suggested priorities for next week
10. Suggested edits to my Active Projects and Master Action List documents

Do not take action for me.
Do not send messages.
Do not schedule anything.
Do not edit source documents unless I approve the changes.

This is the version most people should build first.

Step 7: Add a Manual Confirmation Loop

When Claude gives you the daily brief, reply with:

Accepted:
- 

Completed:
- 

Changed:
- 

Ignore:
- 

Add:
- 

This gives you a clean way to correct the system.

Step 8: Keep It Narrow for Two Weeks

For the first one-two weeks, avoid expanding the system.

Do not add six more sources.

Do not add automations.

Do not make it track your macros, your cat’s emotional state, and the moon phase of your inbox.

Just run:

• Daily brief

• Weekly review

• Master action list

• Active projects

• Important people and companies

If it works, expand.

If it does not work, simplify.

That is engineering and also adulthood, unfortunately. :/

Option 3: The Full Local-Machine Version

This is the version I built.

I have explained my build procedure below. I think you should use this as a guide and do the work of creating what works for you. Building it yourself will teach you how it works and you’ll be able to customize and maintain over time.

This is for people who want the whole thing:

• Local files

• Obsidian vault

• Scheduled pulls

• Logs

• Health checks

• Local models

• External model fallback

• Daily email

• Reply processing

• Diagnostics

• The full little cyber-possum

This is not where I recommend starting.

But if you want the robust version, here is the basic path.

Step 1: Define Your Requirements First

At minimum, define:

1. What inputs the system needs

2. Where the information should live

3. What the system should extract

4. What the system should never do

5. What the daily output should include

6. How often the system should run

7. What should happen when something fails

8. How you will verify it works

If you cannot describe the system, you are not ready to build the system.

Step 2: Create the Obsidian Vault

Use the same vault structure from the manual version:

1. 00 Inbox

2. 01 Daily Notes

3. 02 People

4. 03 Companies

5. 04 Projects

6. 05 To-Dos

7. 06 Writing

8. 07 Context

9. 08 Logs

10. 09 Archive

The difference here is that the system updates the vault for you.

Obsidian is still the source of truth.

Step 3: Create Your Context Files

Inside 07 Context, create the context files you need. Claude stores its own but I have it sync and back up to these context files so that I always have them for use in local LLMs. Mine look like this:

1. Personal Operating Context.md

2. Company Context.md

3. Writing Goals Context.md

4. Current Goals.md

5. System Rules.md

The most important file is System Rules.md.

Use something like this:

# System Rules

## The system may
- Summarize information
- Extract tasks
- Identify follow-ups
- Update Obsidian files
- Prepare daily briefs
- Label easy tasks as EZPZ
- Flag stale projects
- Create draft recommendations

## The system may not
- Send emails without approval
- Send texts without approval
- Schedule meetings without approval
- Delete source information
- Make commitments on my behalf
- Send sensitive information to external models unless explicitly allowed

## Processing preference
1. Use deterministic parsing when possible.
2. Use local model processing when possible.
3. Use external APIs only when needed.
4. Log all model calls.
5. Flag ambiguous information instead of guessing.

Step 4: Build the Input Layer

Start with the least annoying inputs.

Avoid the temptation I aslo fight to start with everything.

Start with:

1. Local text files

2. Meeting transcripts

3. Calendar export

4. Gmail

5. Photos or OCR later

Build one input at a time.

For each input, the system should:

1. Pull new information

2. Save the raw input or a reference to it

3. Extract useful information

4. Update the right Obsidian files

5. Log what happened

If an input cannot be logged, it is not ready… yet.

Step 5: Build the Intake Log

Create a file or database table that records every run.

Each intake event should log:

1. Timestamp

2. Source

3. Files or records checked

4. New items found

5. Items processed

6. Model used

7. Files updated

8. Errors

9. Warnings

Source of truth needs traceability.

Step 6: Build the Processing Layer

The processing layer takes raw information and turns it into structured updates.

It should extract:

1. Tasks

2. Follow-ups

3. Dates

4. Decisions

5. People

6. Companies

7. Projects

8. Risks

9. Opportunities

10. Writing ideas

Each extracted item should include:

1. What it is

2. Where it came from

3. Who is involved

4. Whether action is needed

5. Suggested priority

6. Confidence level

Step 7: Build the Obsidian Update Layer

The system should update files in predictable places.

For example:

• New person found → 02 People

• New company found → 03 Companies

• New project update → 04 Projects

• New action → 05 To-Dos

• New writing idea → 06 Writing

• System event → 08 Logs

Every update should be append-friendly.

Do not let the system casually rewrite your entire knowledge base.

That is how you wake up and discover your notes have magically been organized out of existence, lol.

Append first.

Rewrite only with approval.

Step 8: Build the Daily Brief

The daily brief email is the main interface.

Every morning, the system should produce:

1. Summary of yesterday

2. Top priorities for today

3. Follow-ups I owe

4. People waiting on me

5. People I am waiting on

6. Meetings and deadlines

7. Projects that need motion

8. EZPZ tasks

9. Stale items

10. System health status

The daily brief should be short enough to read before coffee and useful enough to change the day.

Step 9: Build Reply Processing

This is where the system gets spicy.

When I reply to the daily email, the system checks whether I am:

1. Marking actions complete

2. Changing due dates

3. Adding new tasks

4. Rejecting bad suggestions

5. Clarifying ambiguous items

Use a simple reply format:

Completed:
- 

Changed:
- 

Add:
- 

Ignore:
- 

Notes:
- 

The system should parse that reply and update the Obsidian files.

This creates a feedback loop.

Without the feedback loop, the system talks at you.

With the feedback loop, the system starts becoming useful.

Step 10: Add Local Model Processing

Once the basic system works, add local model processing.

Use local models for:

1. Small summaries

2. Low-sensitivity extraction

3. Classification

4. Formatting

5. Duplicate detection

Use external APIs only when:

1. The local model fails

2. The context is too large

3. The reasoning is too complex

4. The output quality matters more than keeping it local

5. No priacy or security inputs are included in.

Step 11: Add Health Checks

The system should check itself.

At minimum, it should verify:

1. Did the hourly pull run?

2. Did each connector work?

3. Did the model calls complete?

4. Did Obsidian files update?

5. Did the daily email send?

6. Were there errors?

7. Were there abnormal outputs?

If something fails, the system should tell you. Immediately.

Step 12: Test With Fake Data First

Before connecting your actual life, test with fake data.

Create some fake data! fake emails, fake meetings, fake people, fake companies.

Make sure the system can correctly identify:

1. A task

2. A follow-up

3. A due date

4. A person

5. A company

6. A project update

7. A completed action

8. A stale item

9. A sensitive item

10. A bad or ambiguous suggestion

Step 13: Turn It On Slowly

Do not connect everything at once.

Week 1:

• Local files

• Manual notes

• Daily email

Week 2:

• Calendar

• Meeting transcripts

Week 3:

• Gmail

Week 4:

• Website, Substack, CRM, photos, and other inputs

Slow roll out ftw.

Step 14: Keep Human Approval at the Edges

The system can:

• Summarize

• Sort

• Suggest

• Draft

• Remind

• Flag

• Update notes

The system should not automatically:

• Email clients

• Text people

• Schedule meetings

• Delete records

• Make promises

• Change strategy

• Decide what matters without review

Step 15: Make the System Earn Complexity

Do not add features because they are cool.

Add features because the system has proven it needs them.

The order should be:

1. Capture

2. Organize

3. Summarize

4. Prioritize

5. Remind

6. Update

7. Automate

8. Optimize

Most people jump straight to optimize.

That is how you end up with a nothing burger.

Full Requirements Trace

REQ-001: Continuous Operation

Requirement: The system shall operate continuously with minimal manual intervention.

Design implementation: Custom application running 24/7 on my Windows machine.

Verification: Confirm the application remains active for 7 consecutive days without manual restart.

REQ-002: Hourly Monitoring

Requirement: The system shall monitor configured input sources at least once per hour.

Design implementation: Scheduled hourly pull from connected services and local files.

Verification: Confirm each configured input source is checked at least 24 times per day.

REQ-003: Input Ingestion

Requirement: The system shall ingest information from required personal and business inputs.

Design implementation: Connectors for Gmail, calendar, meeting transcripts, website data, Substack data, AI chat history, local context files, and notebook/photo inputs.

Verification: Confirm new data from each input source appears in the intake log.

REQ-004: Obsidian as Source of Truth

Requirement: The system shall store processed information in Obsidian as the primary knowledge base.

Design implementation: Obsidian vault used as the structured database for people, companies, projects, writing, context, and to-dos.

Verification: Confirm processed information creates or updates the correct markdown files in the vault.

REQ-005: Action Extraction

Requirement: The system shall identify tasks, obligations, follow-ups, dates, and commitments from incoming information.

Design implementation: LLM-assisted extraction from emails, transcripts, texts, notes, and context files.

Verification: Test against sample inputs and confirm the correct actions, owners, and due dates are extracted.

REQ-006: Duplicate Prevention

Requirement: The system shall update existing records instead of creating unnecessary duplicates.

Design implementation: Entity matching for people, companies, projects, and recurring topics.

Verification: Confirm repeated mentions of the same person, company, or project append to the existing file rather than creating duplicate records.

REQ-007: Unified Action List

Requirement: The system shall maintain a unified action list across all input sources.

Design implementation: Central to-do/action file updated from every intake cycle.

Verification: Confirm actions from email, calendar, notes, and transcripts all appear in one consolidated action list.

REQ-008: Priority Sorting

Requirement: The system shall sort actions by importance, urgency, and ease of completion.

Design implementation: Priority logic that labels high-priority items and marks low-friction tasks as EZPZ.

Verification: Review the daily brief and confirm priorities match actual workload and business goals.

REQ-009: Daily Email Brief

Requirement: The system shall send a daily email brief each morning.

Design implementation: Automated email generated from updated Obsidian files and the current action list.

Verification: Confirm the email sends successfully at the configured time each day.

REQ-010: Required Brief Sections

Requirement: The daily email shall include the most important tasks, active projects, weekly progress, and easy transactional items.

Design implementation: Daily summary template populated from project files, goal files, and the action list.

Verification: Confirm each daily email contains all required sections.

REQ-011: Reply Processing

Requirement: The system shall detect replies to the daily email and update actions accordingly.

Design implementation: Email reply parser reviews responses for completed actions, changed actions, and new actions.

Verification: Reply to the daily email with test updates and confirm the action list changes correctly.

REQ-012: Local-First Processing

Requirement: The system shall use local model processing when possible.

Design implementation: Ollama handles small-context or lower-sensitivity processing tasks.

Verification: Confirm eligible tasks are routed through local models before external APIs are used.

REQ-013: External Model Fallback

Requirement: The system shall route larger or more complex tasks to external LLM APIs only when needed.

Design implementation: Fallback routing to Anthropic or GPT API depending on task type and model requirements.

Verification: Confirm external API calls occur only when local processing fails or the task exceeds local capability.

REQ-014: Audit Trail

Requirement: The system shall produce an audit trail of intake, processing, routing, and output events.

Design implementation: Logs generated for input pulls, model calls, file updates, email sends, and errors.

Verification: Confirm logs exist for each major system action.

REQ-015: Failure Alerts

Requirement: The system shall notify me when a component fails or returns abnormal results.

Design implementation: Health checks and error notifications with diagnostic information.

Verification: Simulate connector failure and confirm the system sends an alert with useful diagnostics.

REQ-016: Human Approval for External Actions

Requirement: The system shall not autonomously send messages, make commitments, or act on my behalf without human approval.

Design implementation: Output limited to summaries, reminders, sorting, and draft-level recommendations.

Verification: Confirm no outbound emails, texts, calendar changes, or client messages are sent without manual approval.

REQ-017: Sensitive Information Handling

Requirement: The system shall treat sensitive information differently from generic task information.

Design implementation: Sensitive inputs routed with stricter processing rules, local-first handling, and limited external exposure.

Verification: Confirm sensitive test inputs are not sent to external APIs unless explicitly allowed.

REQ-018: Maintainability

Requirement: The system shall be maintainable by me without requiring a full engineering team.

Design implementation: Plain-language logs, simple configuration files, Obsidian-readable outputs, and diagnostics that can be pushed back into Cursor or Claude Code.

Verification: Confirm I can identify, troubleshoot, and repair a common failure without rewriting the whole system.

Design Constraints

The system has a few hard constraints:

• Obsidian is the source of truth.

• The system must be useful even if one input source temporarily fails.

• Local processing is preferred when possible.

• External LLM calls are intentional, not automatic for everything.

• The system can summarize, sort, and remind, but it cannot make commitments for me.

• The daily email is the main user interface.

• If the system fails silently, the system has failed.

Closing

Memory improves when we process information more deeply than just storing it.11 I encourage people to build a system that allows you to write by hand while taking advantage of the cognitive load reducing benefits of an automated second brain.

Good luck on your build and drop a comment if you end up using or building a second brain!

~d

The Updraft

Writing on leadership, management, and emotional intelligence. Occasionally, like today, writing on the systems that make good management and leadership possible.

I founded and own Kestryl Edge, LLC a training company dedicated to forging the best leaders possible.

Acknowledgments

Photos generated from ChatGPT using my notes and gpt 5.5.

It’s always sunny meme shamelessly copied from knowyourmeme.

References

Gurus, vibe-coaches, posers,… turn back now.

Self-Care as portrayed by pop-culture is horse shit. I will not argue for the bubble-bath industrial complex here. Nor for the cold-one (or six) before the family is acknowledged.

Leadership demands consistency and resilience. Success demands not giving up.

In order to survive the long haul towards betterness, we need to take care of, and love, ourselves.

Here’s the BLUF (Bottom Line, Up Front) for today’s literature review essay:

• Leaders who protect their own resources lead in more health-supportive ways.12

• Resiliency isn’t a trait, it’s a habit of resource management capability. 345 6

• Concrete, observable routines work. Abstract exhortations don’t. 789

• Self-care and self-compassion make leaders more useful, more stable, and more available. The evidence is strong in some places and uneven in others. ⁸ 10

To sleep perchance to dream…

I struggle with impulse control. It’s something I know about myself and not everyone sees. I like to move quick. To solve problems.

Virgil guiding me through my own layers of hell would no doubt show me a layer where I know something is wrong, someone mad at me, a mistake I made is left uncorrected. I have full knowledge of it. And am held in a conscious stasis… stuck and unable to do anything about it.

All leaders and managers have ticks and triggers that spur them into action. Into speaking their mind.

And, as modern media shows us every day, those who speak first, speak loudly, and act out of emotion, lose. End up appearing childish, misinformed, hasty, etc.

When I started the research for this essay, what became clear to me was that the most supported conclusions in self-care as it related to management and leadership are what is observed when self-care is not present.

Not what we garner when it’s there, but the consequences of its absence.

A 2020 JAMA Network Open study, physicians rated their immediate supervisors on general effectiveness characteristics. Those supervisors independently reported their own burnout, fulfillment, self-valuation, and sleep quality.11

Each 1-point increase in self-reported burnout was associated with a 0.19-point decrease in independently rated leadership behavior. Simply put, the more burnt someone self-reported, the shittier their leadership was rated. ¹⁰

We all think we’re above the law when it comes to these sorts of stats. That somehow they only apply to the participants we measured. Not everyone else.

“Well!, I’ve been getting 5 hours of sleep for years. It’s just how much I sleep. I’m different than everyone else.”

Positive thinking is powerful. It is not powerful enough to exempt us from biology.

The sleep literature, one of my favorite literature categories, provides some of the strongest evidence on how leader self-care failures degrade leadership behavior.

A daily experience-sampling study, poor nightly leader sleep quality predicted more daily abusive supervision via ego depletion which in turn reduced subordinate unit work engagement.12

Similarly, a subsequent study found that leader sleep devaluation - leader behaviors signaling that sleep should be sacrificed for work - undermined employee sleep quality and linked to higher subordinate unethical behavior across other work domains.13

If we needed more, a broader decision quality study showed multi-night sleep restriction increased dishonest decision making, and a 2025 review concluded that sleep loss impaired core decision processes such as value sensitivity and increases decision noise.1415

Skip your sleep and your team suffers. They get a grumpier leader, worse norms, and poorer decisions. The damage does not stay politely inside your skull.

I know myself all too well. I am one bad night of sleep away from insufferability. You can’t Red Bull your way out of the resting-Dan-face of a poor night of rest with no patience in the bank. So, I try for 7.5 hrs every night. Or else I join the cohort of impulsive leaders who succumb to their depletion and lash out. Rested, healthy, and late to work is better than assholish, grumpy, and fired.

Brandi Copeland and I discussed employee engagement trends on the Kestryl Edge Podcast recently. Brandi shared how employee disengagement is at an all-time low. Depending on the source, reports say only 23%-31% of employees are engaged at work.1617

The underlying sentiment is something we can all identify with: broadly, across America, people feel detached and are giving less shits.

On the episode in question, Brandi and I chatted about solutions. Mainly dancing with the prescription that engagement comes from listening, understanding, and the precursor habits of building trust.

So here’s another solution, it seems.

Leaders who want engagement,

go the fuck to sleep.

There are two things you can do today that will make you better tomorrow.

1. subscribe.

2. go to bed.

Be the leader future-you will be proud of.

Subscribe now

Thus conscience doth make cowards of us all

There is a canon event in every new manager’s life: the first closed-door conversation where someone hands you their pain and you mistake holding it for helping.

You’re sitting there in your new chair. In a newly decorated office. An employee, new to you, comes in, closes the door, and begins to share problems, grievances, gossip, beef, real issues, bonafide conundrums, real world happenings.

As the newly minted “supporter of people,” you listen. Actively and with care. Investing in the emotions, investigating in the origins, and inventing solutions and plans to stop the bleed of this problem.

You’re the manager after all.

It’s your job to fix this.

Again.

Again.

And again.

Fixing one person’s problem spawns another and there’s a chain reaction of mess. Senior leadership wants to know what’s going on and gives you their ten cents on what you should have done even though you did everything right and they just didn’t listen the first time you told the story.

But, why argue?

And you go home tired. Exhausted. Not wanting to talk to another human because you’re drained. Zapped. Energy: gonzo.

The event is becoming a manager and learning how to set boundaries with your team for what of theirs you take on and what stays theirs.

The event is learning to regulate your empathy.

Empathy has a line.

I won’t pretend I know exactly where that line is. It’s somewhere between giving a singular shit and going home a brain-mush zombie. When we absorb the feelings of others and hyper-fixate on their experience, we degrade ourselves. Feeling too deeply. Lost in the sauce.

The literature gives us a better tool than numbness: self-compassion.

Self-compassion is self-kindness rather than harsh self-judgment, common humanity over isolation, and mindfulness rather than over-identification with painful thoughts and feelings. Unlike self-care, it is solidly defined with borders. The literature knows what it is and has colored the boundaries in with a swath of research and data. As a result, the evidentiary base for self-compassion and its benefits is stronger than for self-care.181920

Broadly, people who practice self-compassion are less threat-reactive around the self. Their self-compassionate responding makes it easier to face negative information without becoming engulfed or defensive.2122

Even brief self-compassion training has been shown to reduce stress responses. Related work found lower stress reactivity among more self-compassionate participants during repeated psychosocial stress.2324

Self-compassion does not simply make you “feel better.” It changes how strongly we are driven into fight, flight, collapse, or defensive self-protection under interpersonal pressure. ^{20 21}

The benefits of self-compassion also include improved emotion regulation and psychological flexibility. We are able to give ourselves a less shaming, less avoidant way to process difficult emotions.2526

And the piece of information that makes me rethink my life so far?

Empathy training can increase negative affect and activate neural regions associated with sharing pain. Compassion training produces a different pattern associated with positive affect and prosocial motivation. Compassion and perspective-taking are associated with lower burnout and affective symptoms. Self-other emotional fusion is associated with worse outcomes.2728

Empathy, when overdone, makes us feel the negativity of those around us in a way that degrades the self.

Compassion allows us to be there genuinely and perspective-take without succumbing to emotional contagion.

The literature does not support a simple “more empathy is always better” narrative. Several studies suggest unregulated empathy can be harmful. A safer conclusion is that the healthiest form of caring requires compassion, perspective-taking, and self-regulation. Not just emotional resonance. 2930 ²⁵

This is where the research gets annoying.

These words we find in the literature can mean so many things. One of the things any deep-diver discovers when spelunking around the leadership literature is that… it’s not great. Words are defined willy-nilly. Measurement standards are unique to each paper. Connection of evidence to cause across time is difficult.31 ⁹

When I used to work in quantum dot nanoparticles for luminescent solar concentrators, windows that generated electricity, the field published a standards paper. A conglomerate paper where authors were invited to set the mathematical standards and definitions the field would use from then on. With performance equations set into stone, the field could advance and compare results across different laboratories more easily.

People are harder to study than quantum dots.

Where the literature interconnects, I have compiled solid conclusions and recommendations for leaders going forward.

Train the thing directly. Self-compassion is teachable. Targeted training can increase not only self-compassion but also mindfulness, compassion for others, and broader well-being. ^{16 22}

Stop confusing empathy with emotional possession. The goal is to remain empathically available over time. Toward this end, the literature points away from indiscriminate affective contagion and toward compassion, perspective-taking, and self-regulation. ^{24 25}

Practice relational skills early, often, and consistently. Mindful communication for physicians and loving-kindness training for doctors both improve relationally relevant outcomes. For leaders, mindful leadership and emotional-skills cultivation improved leadership-related behaviors and reduced some burnout markers. 32333435

Stop framing self-care as private indulgence. The strongest self-care papers do not frame self-care as the singular hot tub dip in Q2. It is defined as a pattern of support, balance, awareness, and sustainable professional functioning. It’s not optional comfort behavior, the pizza and ice cream after a week of no sleep. It’s habitual capacity building and burnout prevention. ²⁹36

And, for the love of all things holy, we need to stop pretending individual habits can outmuscle a toxic system. Individual practices cannot substitute for organizational reform. Primary studies repeatedly identify time pressure, workload, and structural constraints as barriers. We again find that individual actions to wellness can only go so far when you’re in a hellscape work environment that perpetuates unhealthy behaviors and toxic standards. 37 ⁹ 38

So …

I have a theory. I can’t prove it.

We all know leaders who avoid empathy like touching it will melt them. I theorize they did not start their career cold. I think they were once too open.

Too absorbent. Too willing to make every problem their problem.

Then they burned out.

And because no one taught them boundaries, they built walls.

They do not refuse to feel because they are strong.

They refuse to feel because feeling once cost them too much.

They hide from others to avoid confronting their own pain

Toxic outward as a cure for the poison within.

to take arms against a sea of troubles

Something about meditation has always felt so counterproductive to me.

Why sit with your problems when you could be out there trying to kill them?

Remember when I said my hell was knowing I could make a change and being unable to act? Why would I impose this state of suspension upon myself.

Trust me. The irony of this post and my self-identified weaknesses is not beyond me.

Yet sitting still is work. Rest is productive. I can feel it after a particularly epic nap. My body comes back more whole. Calm. Blood pressure relaxed. Tension melted into the couch I begrudgingly pull myself out of. Dogs looking up at me, offended, wondering why I would ever get up.

They didn’t ask me to, after all.

CrossFit legend Noah Ohlsen talks about downtime between intense training sessions. Reading. TV. Video games. Doing as little as possible.

The ideal athlete trains hard for several hours a day and spends the rest of the day weighted disproportionately toward nothing.

Resting.

Recovering.

Pro athletes can still feel guilty doing this. Chasing acute performance comes with the feeling that rest is laziness. That if they are not doing more, they are falling behind.

I get it.

Rest without shame is something I struggle with too. I know it would unlock higher performance when I am “on,” instead of leaving me in that sluggish march where I’m not done, not worthy of love yet, but not alive either.

I know it would unlock higher performance when I am “on,” instead of leaving me in that sluggish march where I’m not done, but I’m not alive either. ^{3 4}39

Much like we are not born brave. And to stand up with bravery does not require us to feel what we project.

Habits are our keeper.

Resilience is the sum of the habits that serve us. And therefore building resilience comes after building personal infrastructure to support outcomes that look like resilience. ^{5 3}40

Resilience is built.

With this regard their currents turn awry, and lose the name of action

I do not think self-care is soft.

I think softness develops when leaders confuse exhaustion for virtue. When they call depletion commitment. When recovery is viewed a character flaw.

I know this because I am not above it.

I want to move. Fix. Prove. Earn. Win. Be useful. Be needed. Be undeniable.

And my body keeps interrupting my soliloquy.

Sleep matters. Recovery matters. Boundaries matter. Self-compassion matters. Not because they make me gentler in some decorative, corporate-retreat way. They matter because without them I become less honest, less patient, less generous, less regulated, less able to stay with people when staying with people is the job.

The leader who cannot stop cannot recover.

The leader who cannot recover cannot regulate.

The leader who cannot regulate cannot remain kind and sturdy under pressure.

And the leader who cannot remain kind under pressure becomes the pressure.

Which, I keep coming back to.

Self-care is not escape from the work. It is what keeps me from turning the work into an omni-directional weapon.

It is not the cold-one before the family is acknowledged. It is acknowledging the family.

It is not the bubble bath industrial complex. It is going to bed before my ego starts writing checks my nervous system cannot cash.

It is not disappearing from responsibility. It is becoming someone who can carry responsibility without making everyone else acknowledge me and pay for the weight with imposed shame.

We do not need leaders who worship at the altar of grind until there is nothing left but caffeine, resentment, and our consequences.

We need leaders who can do the boring holy work.

Sleep.

Pause.

Reflect.

Repair.

Ask what belongs to them.

Ask what belongs to the system.

Ask what they are carrying because it is theirs, and what they are carrying because being exhausted makes them feel important.

The brutal little joke of it all.

Sometimes the most disciplined thing I can do is nothing.

Not forever. Not as avoidance. Not as surrender.

But long enough to come back human.

Long enough to not confuse urgency with wisdom.

Long enough to not confuse empathy with absorption.

Long enough to not confuse resilience with refusing to bleed.

Because action without recovery curdles into reaction.

Care without boundaries curdles into resentment.

Leadership without self-compassion curdles into control.

And control, eventually, curdles into cruelty.

So, to self-care or self-cannot!?

That is the question.

And I hate that the answer is sleep, boundaries, compassion, and rest.

But here we are.

~d

below is the holy work for those of us learning to worship at the Church of Nothing.

The Work

1. Protect sleep and recovery as non-negotiable performance conditions. ^{11 12 13}

2. Train leaders in observable support behaviors rather than generic empathy language. ^{6 9}

3. Use mindfulness and self-leadership training as capacity builders for self-regulation and detachment. ^{8 43}

4. Measure and review leader well-being regularly.wind 41

5. Connect leader self-care to work design. ^{37 38}

A concise implementation cadence :

First month

• Baseline leaders and teams on burnout, sleep impariment, and one support-behavior measure. Identify high-strain teams. 42

First Quarter

• Train managers in family-supportive and health-oriented behaviors; introduce delayed-send and boundary norms. ^{7 9}

First Half-Year

• Offer evidence-based mindfulnedd/self-leadership training for managers. 43

Ongoing

• Review manager load, after-hours work, and interruption patterns together with well-being metrics. ^{37 42}

About

I am the founder of Kestryl Edge, LLC. A company that teaches emotional intelligence and leadership to teams who face high consequence environments.

The Updraft is my personal space to write, reflect, learn, and document my personal journey building.

For quarterly company updates, check out Kestryl Edge on Substack.

We have a weekly podcast that’s all about leadership and EQ.

Reach out with questions, and welcome to The Updraft.

Subscribe now

References

Photos generated with Chat-GPT 5.5 with prompts built with notes from my essay.

The standard hierarchy of teams and corporate structures puts leaders in a spot beyond feedback and awareness.

For so long have we treated leaders as individuals beyond critique that we’ve built entire institutions around protecting their decisions, their character, their ego.

You’re not like that.

You are a leader who is open to growth and the uncomfortable truth that maybe you don’t have all the answers. Maybe you’re not perfect.

And in that imperfection we find beauty and invitations to greatness.

Tanu and I met on Substack and have become fast friends bonding over our shared love of leadership.

This is an article about how you can find your blind spots and how you can train to become better.

Tanu - Invisible Lessons

Seven Ways to Catch What You Can’t See

Cover your left eye. Hold a pen at arm’s length, fix your right eye on something across the room, and drift the pen slowly toward your nose. At a certain point the tip disappears, not into a smudge, but into nothing. The wall simply closes over the place where it used to be.

That’s the spot where the optic nerve exits the retina, a patch with no light-sensing cells. By rights you should walk around with a hole in your vision. You don’t, because the brain studies the surrounding texture and paints the gap in to match, the same cream as the wall, the same grain of the floor. The missing information gets replaced with a confident guess so seamless you never notice the seam.

This is the uncomfortable truth about a blind spot, the literal one and the career-ending kind: it has never once felt like ignorance from the inside. It feels like a finished picture. You can’t stare it down, the eye is built to keep it from you. But you can learn the conditions under which yours tends to surface.

Here are the seven ways to identify your own leadership blind spots.

1. Follow the heat. The fastest way to identify is your own defensiveness. Notice the topic where your pulse jumps before the sentence is even finished, the rebuttal or reaction that comes up in your head while the person is still talking. We don’t get defensive about things that are false. We get defensive about things that are true and unwelcome. The flush of irritation is not noise to manage; it’s the signal of something deeper that needs to be surfaced.

2. Triangulate the repetition. One person calling you “intense” is their opinion. The same word surfacing from a peer in 2019, a direct report in 2022, and your spouse last Tuesday is data. Blind spots travel with you across teams and jobs precisely because the common factor is you. Listen for the criticism that keeps finding you in different rooms, in different decades, from people who’ve never met.

3. Audit the silence. What has your team stopped saying? Not what they say but what’s gone quiet. The pushback that used to come and doesn’t, the questions that dried up, the meeting where everyone nods a little too easily. Silence creeps in slowly and it can be hard to notice when you are chasing targets. The response to pressure situations might be well-intended and not malicious. But people learn every time you do things like show impatience, make decisions alone, loop in someone less, all in the interest of time. Pretty soon you’ve got a room that agrees with you, and it feels like alignment when it’s often an echo chamber you built without meaning to. The trouble with an echo chamber is that from the inside, it just sounds like being right.

4. Read your dismissals. Open the mental file where you’ve written someone off with “they just don’t get it.” Check who’s in it? The colleague you don’t trust, the team member whose concerns you’ve decided are really about something else, the peer you’ve quietly labeled as difficult. That file is less a record of people who are wrong and more a record of feedback you’ve found a reason not to hear. Reopen one case. Argue the other side as if you had to win it.

5. Interrogate your strengths, not your weaknesses. A blind spot almost never shows up as a flaw. It disguises itself as the trait you’re proudest of. Decisiveness reads as “doesn’t listen.” High standards that suck the life out of people meant to meet them. Take the quality you’d put at the top of your own strengths list and ask what it costs the people downstream of it. Every overused asset casts a shadow, and the shadow always falls on someone else.

6. Mind the gap between intent and impact. You know what you meant. Your team only ever experiences what you did. Pick one recent moment, maybe a terse reply or a decision made fast, and ask how it likely landed. Hard to strip off the generous intention only you can see but what you intend and how it is perceived is the distance where the blind spot could be festering.

7. Think of your last surprise. When did someone last tell you something about yourself that genuinely surprised you…not flattered you, surprised you? If you have to reach back years, that’s not evidence you’ve run out of blind spots. It’s evidence that you might not be as approachable as you think and people around you have stopped communicating with honesty.

Worth Sitting With

You’ll notice none of these asks you to see the blind spot directly. They ask you to watch for its effects, the heat, the silence, the surprise that never comes. Raising consciousness was never about seeing everything at once. It’s about no longer trusting the parts of the picture that feel a little too smooth.

Dan - The Updraft

A Bias for Action

Early in my career a mentor pushed me to approach problems with a bias for action. The phrase comes from Peters and Waterman’s In Search of Excellence, the first trait they found in companies that executed instead of studying themselves to death. Peters’ own gloss: don’t just stand there, do something.

There’s a line in science, usually credited to the chemist Frank Westheimer: a couple of months in the lab can save you a couple of hours in the library. It’s sarcasm. A dig at people who rush to experiment before they’ve done their reading. My problem was the exact inverse. I’d spend the hours in the library and never get to the lab. I’d perseverate, think and refine and refine, and not trust myself enough to put the idea into an actual experiment. And the reality is that if you never apply what you’re learning, you can burn a week reading when a thirty minute experiment would have told you everything you needed to know.

Your blind spots work the same way. Tanu’s list is your hour in the library. It’s necessary. Write down the feedback and the areas you think you could be better, then go run the experiments.

Here’s one of mine. I get frustrated in ineffective meetings. Every time, lol. My blind spot is that people read it on my face instantly, and the sarcasm is obvious the second I open my mouth. So I ran an experiment. Now I take physical notes on what’s happening and what I’m thinking. I put my brain to work on the arguments, the risks, the decisions, what’s actually at stake for me. It slows me down, drops me into active listening, and makes me think critically about the room and respect the people in it, instead of being an insufferable bitch about it.

That it’s a small experiment matters. Amy Edmondson studied failure for years and concluded that “fail fast, fail often” misses the point. A failure is only worth anything when it’s what she calls an intelligent failure: you’re in new territory, chasing a real goal, testing a genuine hypothesis, and you’ve kept the experiment as small as it can be while still teaching you something. That’s the bar. Not reckless failing. Small, deliberate bets on yourself.

Everyone’s blind spots and everyone’s experiments look different. They share one thing. If you don’t run the experiment, nothing changes. So devise a few ideas and test them. Fail as fast and as small as you can. Through intelligent failure you learn the thing the library was never going to teach you, and you iterate toward better fast.

Swords Have Two Sides

Tanu’s fifth point told you to interrogate your strengths instead of your weaknesses. This is what to do next once you find one.

Your biggest professional strength is usually your biggest weakness too. Robert Kaplan and Robert Kaiser have a name for what happens when you forget that. They call it lopsided leadership, and after running a 360 assessment on thousands of managers they found we reliably overdo the behaviors tied to our strengths and underdo the opposing ones that would balance them. They even named the tension most of us live inside: forceful versus enabling. The more forceful a leader is, the less enabling they tend to be. One side of the sword, sharpened until the other side rusts.

So be careful. If you set out to cover your weakness and push too far, you dull your strength and lose your edge.

Find a mentor you trust. Someone who knows you and sees the best in you. Someone who will give you the hard truth and you think “yeah, they’re right,” not “well, fuck you too, Brenda.”

Tasha Eurich studied how people actually become more self-aware and found it almost always runs through one kind of relationship. She calls them loving critics: people who have your interests at heart and are still willing to tell you the truth. That’s who you’re looking for. Not a cheerleader, not a critic. Both at once.

Prioritize a mentor who is great at your weakness and understands your strength. That combination is what lets you sharpen both sides of the sword without grinding one of them down.

Here’s mine. I’m confrontational and direct. It serves me. I resolve problems, I say what I think, I move toward action. It also costs me. I struggle to move fast without making the people around me pay a relational price for my speed. So I look for mentors who can hold relationships together inside chaos and tension. I stay action oriented, I use my directness to get shit done, and I pick up tools for keeping the people around me intact while I do it.

Overcompensate and you dull the strength. You stop getting shit done. Under-compensate and you never cover the liability the strength carries.

The work is the balance, and you can’t see your own balance from the inside. That’s what the mentor is for.

The sword doesn’t get safer when you blunt it.

It just gets useless.

~ d

The Authors

Tanu Tiwari is a leadership strategist, certified coach, and founder of The Conscious Leader Co., with more than 18 years corporate experience across Fortune 500 companies, global organizations, and high-growth startups. Her forthcoming book, Disengaged, makes the case that checked-out teams are an environment problem rather than a people problem, and she writes about the invisible leadership patterns that shape how people show up at work, with Invisible Lessons.

Dan Korus is the founder of Kestryl Edge, a leadership development practice that trains emotional intelligence for operations-heavy teams in high consequence environments. He hosts the Kestryl Edge podcast and writes The Updraft, a newsletter on evidence-grounded leadership without the corporate filler.

Subscribe now

References

• Edmondson, Amy C. Right Kind of Wrong: The Science of Failing Well. New York: Atria Books, 2023. https://www.simonandschuster.com/books/Right-Kind-of-Wrong/Amy-C-Edmondson/9781982195069

• Eurich, Tasha. “What Self-Awareness Really Is (and How to Cultivate It).” Harvard Business Review, January 4, 2018. https://hbr.org/2018/01/what-self-awareness-really-is-and-how-to-cultivate-it

• Kaplan, Robert E., and Robert B. Kaiser. Fear Your Strengths: What You Are Best at Could Be Your Biggest Problem. San Francisco: Berrett-Koehler Publishers, 2013. https://kaiserleadership.com/big-ideas/article/fear-your-strengths

• Kaplan, Robert E., and Robert B. Kaiser. “Stop Overdoing Your Strengths.” Harvard Business Review 87, no. 2 (February 2009): 100–103. https://hbr.org/2009/02/stop-overdoing-your-strengths

• Peters, Thomas J., and Robert H. Waterman Jr. In Search of Excellence: Lessons from America’s Best-Run Companies. New York: Harper & Row, 1982. https://en.wikipedia.org/wiki/In_Search_of_Excellence

• Westheimer, Frank H. “A couple of months in the laboratory can frequently save a couple of hours in the library.” Widely attributed aphorism. “Frank Westheimer,” Wikiquote. https://en.wikiquote.org/wiki/Frank_Westheimer

If you manage a team doing important work, safety-critical work, expensive work, or reputational-risk work, then some meetings are necessary and should be navigated with care.

Meetings are control surfaces.

A good meeting changes the state of reality.

Remember, if nothing changed, you didn’t have a meeting.

So! Here are the tools: specific ways to shape a meeting’s outcome without becoming the person everyone privately refers to as “that guy.”

1. Write the outcome before you invite the humans

Before you schedule anything, write this sentence:

“We are meeting to ______.”

If you cannot finish that sentence cleanly, do not send the invite.

Good answers:

• “We are meeting to decide whether to delay launch.”

• “We are meeting to choose between three staffing plans.”

• “We are meeting to surface the top risks before we commit budget.”

Bad answers:

• “Sync.”

• “Touch base.”

• “Discuss.”

• “Quick huddle.”

A meeting without an outcome is just a calendar-shaped fog machine.

For high-consequence teams, the outcome should be specific enough that someone can tell whether the meeting worked. Not whether people spoke. Not whether the senior person nodded. Whether the work moved.

“Decision needed: Launch date for Project Peregrine.”

Beautiful. Adult. Slightly arousing to people who respect calendars.

2. Send the lore drop

People make better decisions when they are not forced to reconstruct the entire history of the problem live, while Diva Dave shares his screen and says, “Can everyone see this?” for the fourth time.

Send the lore before the meeting.

The lore is not a 900-page archaeological dig. It is the useful backstory:

• Why are we here?

• What changed?

• What decision is needed?

• Who owns the decision?

• What are the real constraints?

• What happens if we do nothing?

This matters especially when the stakes are high. You do not want people learning the context and making the decision in the same breath. This is precisely how groups end up confidently choosing the organizational equivalent of gas station sushi.

Example:

Purpose: Decide whether to proceed with the current launch date.
Lore: The team identified two unresolved testing risks last Thursday. Customer commitments begin next month. Finance needs a final date by Friday.
Decision owner: Zardovan.
Desired output: Launch, delay, or launch with conditions.

Now people arrive with thoughts already thunk.

3. Pre-wire the room

Pre-wiring is what happens before the walls go up.

In meetings, it means talking to key people before the meeting so the actual meeting is not the first time anyone hears the proposal, objection, data, or political landmine.

It sounds shady. It is not shady. It is responsible leadership.

Before a high-stakes decision, talk 1:1 with the people who can block, improve, or detonate the outcome. Ask them what concerns they have. Ask what would make the decision easier. Ask what they need to see.

You are not asking for blind agreement. You are making sure the room does not blow up on you.

Pre-wire those people.

If the first serious objection appears during the meeting, that may be bad luck. If the seventh serious objection appears during the meeting, that signals insufficient preparation on your part.

4. Frame the problem before the room frames it for you (yee-ing the haw before the haw yees you)

Whoever defines the question controls much of the outcome.

“What should we do?” creates chaos.

“Which of these three options best fits our risk tolerance, timeline, and staffing reality?” creates a decision lane.

The first version invites everybody to dump their favorite pet idea onto the floor.

The second version gives the room boundaries.

Done honestly, this is not manipulation. Your job is not to let every conversation spiral beyond productive bounds.

e.g. “Given our staffing, deadline, and customer exposure, I see three viable paths.”

Then list them. Have them written on your slide already.

Make sure the options are real. Do not create one good option and two scarecrows stuffed with budget dust and b.s. gantt charts. People can smell that. Especially the quiet thinkers in the room. They know.

5. Put your preferred option in daylight

If you have a recommendation, say so.

Too many managers pretend to be neutral while quietly praying folks will decide in their favor after presented a reasonable data set.

“I’m open to anything,” they say, while the deck somehow spends 26 slides explaining why Option B is basically a civic duty.

Just say what you think.

“My recommendation is Option B because it reduces launch risk without blowing up the customer timeline. I welcome alternatives and adjustments.”

That is clean. People know where you stand. They also know disagreement is allowed because you invited them to test it.

Guide the room without pretending you floated in as a sweater vest dawned paragon of neutrality.

6. Use time as a pressure dial

Time changes the kind of thinking people do.

A 15-minute meeting forces prioritization.

A 90-minute meeting invites wandering, throat-clearing, legacy grievances, and someone saying, “Just to piggyback…”

For high-consequence work, do not default to short or long. Choose the time based on the type of thinking required.

• Need a decision on a known issue? Short meeting.

• Need to explore messy unknowns? Longer meeting.

• Need to review context? Send a pre-read and spare everyone the live audiobook.

“We have 20 minutes for this decision meeting. Let’s avoid further brainstorming.”

Or:

“We have 75 minutes because the problem is still underdefined and we need room to map it.”

Time is a container and can be used to your advantage.

7. Manufacture shared understanding, not fake consensus

There is a dangerous little spell people cast in meetings:

“It sounds like we’re aligned.”

Sometimes that is true.

Sometimes that means three loud people agree, two people are confused, one person is silently horrified, and the person with the most relevant expertise is waiting for oxygen.

Unless you’re feeling evil, your job is not to pretend the room agrees. Your job is to find out what kind of agreement you actually have.

• “Before we call this aligned, I want a quick round. Support, oppose, or concerns?”

• “Is anyone seeing a risk that would change the decision?”

• “Who has to execute this and thinks we’re missing something?”

This is where mature teams separate themselves.

You do not need everyone ecstatic. You need to know whether the decision is understood, owned, and survivable. You need to know what you don’t know.

8. Pull objections into the light early

Unspoken resistance is expensive.

It does not disappear because you avoided eye contact with it. It goes underground, grows mushrooms, and reappears three weeks later as “concerns from the team.”

Ask for objections directly.

Not performatively. Not “any concerns?” while already closing your laptop.

You have to actually ask.

That last one is a bit spicy. Spicy can be fun. Use responsibly.

Any leader worth their salt knows objections are not disloyalty. Objections are part and parcel with high performance the safety systems that uphold it.

9. Manage the room like it matters

Open discussion is not always noble. Sometimes open discussion is just open mic night for the highest verbal metabolism.

As uncomfortable as it can be asking someone to pipe down or pipe up… you have to manage participation.

Pull in the quiet experts. Contain the dominant voices. Stop drive-by sarcasm. Kill disrespect early.

If someone has not spoken and they own a key part of the work, invite them in.

“Jordan, you’re closest to implementation. What are we missing?”

If someone is taking too much air:

“That’s useful. I want to pause there and hear from people who haven’t weighed in.”

If someone is being rude:

“That doesn’t fit how we’re going to work this conversation. Rethink and rephrase, or we’re moving on.”

• No personal attacks.

• No surprise data grenades.

• No hidden vetoes after the decision.

• No pretending silence means consent.

High-trust rooms do not happen because everyone is nice. They happen because someone protects the room.

10. Write the decision where everyone can see it

There is power in the pen.

If you write the decision live, the room has something to react to, edit, confirm, or challenge.

This reduces the classic meeting disease where everyone leaves with a different movie playing in their head.

Capture:

• Decision made

• Owner

• Due date

• Open risks

• Follow-up actions

• Unresolved questions

• Use plain language. No corporate incense.

Bad note:

“Team aligned on next phase enablement.”

Good note:

“Decision: Delay launch by two weeks to complete testing. Gonzobo owns revised timeline by Thursday. Maldorfus owns customer communication draft by Friday.”

One of those can run a team.

The other belongs in a cursed slide deck.

11. Make the decision rule explicit

A lot of meeting weirdness comes from nobody knowing how the decision is being made.

• Are we voting?

• Advising?

• Seeking consensus?

• Giving input to one decision owner?

• Letting the loudest interrupter slowly absorb the room?

Say the rule out loud.

This prevents quiet power grabs and post-meeting revisionist history.

A decision without a decision rule is usually just vibes.

12. End with the next physical action

Never end a serious meeting with “great discussion.”

That phrase should set off sprinklers.

End with the next physical action. Not a concept. Not a hope. Not “circle back.”

A person doing a thing by a time.

If nobody owns anything, the meeting produced vapor.

If everyone owns something, nobody does.

If Dave owns it, Godspeed, and please put it in writing.

The line between leadership and dark arts

Yes, you can steer meetings.

You can pre-wire stakeholders. You can frame the decision. You can control the option set. You can use time pressure. You can write the conclusion as it forms. You can pull objections into the light at the right moment.

These tools work.

That is exactly why you need to use them with positive intentions.

The goal is not to trick the room into your preferred outcome. The goal is to help the room make the best available decision with the right people, the right context, and the right amount of pressure.

Sometimes that means pushing.

Sometimes that means slowing everything down.

Sometimes that means saying, “We are not ready to decide.”

That sentence can save millions of dollars, months of rework, and several people’s nervous systems.

A strong manager knows meetings are not about appearing in control. They are about creating the conditions where reality can enter the room without getting tackled by ego, politics, confusion, or Gusko from Finance saying “just playing devil’s advocate” for sport.

Meetings are a leadership instrument.

Play them badly and no one will want to listen.

Play them well and the team leaves sharper than they arrived.

No decision, no meeting.

No owner, no outcome.

No agendy, no attendy.

- Dan

Read Other Favorites from The Updraft

References

Rogelberg, Steven G., Desmond J. Leach, Peter B. Warr, and Jennifer L. Burnfield. “‘Not Another Meeting!’ Are Meeting Time Demands Related to Employee Well-Being?” Journal of Applied Psychology 91, no. 1 (2006): 83–96. https://doi.org/10.1037/0021-9010.91.1.83

• Argues that meeting load and meeting quality affect employee well-being, especially when meetings feel like interruptions rather than useful coordination.

Nixon, Carol T., and Glenn E. Littlepage. “Impact of Meeting Procedures on Meeting Effectiveness.” Journal of Business and Psychology 6 (1992): 361–369. https://doi.org/10.1007/BF01126771

• Provides claims about agendas, action planning, task focus, timeliness, open communication, and leader impartiality as drivers of effective meetings.

Leach, Desmond J., Steven G. Rogelberg, Peter B. Warr, and Jennifer L. Burnfield. “Perceived Meeting Effectiveness: The Role of Design Characteristics.” Journal of Business and Psychology 24 (2009): 65–76. https://doi.org/10.1007/s10869-009-9092-6

• Explores how meeting design matters, especially agenda use, attendee involvement, and practical meeting conditions.

Kauffeld, Simone, and Nale Lehmann-Willenbrock. “Meetings Matter: Effects of Team Meeting Communication on Team and Organizational Success.” Small Group Research 43, no. 2 (2012): 130–158. https://doi.org/10.1177/1046496411429599

• Argues that what people actually do in meetings, including problem-solving, action planning, complaining, and criticizing, predicts team and organizational outcomes.

Lehmann-Willenbrock, Nale K., Joseph A. Allen, and Simone Kauffeld. “A Sequential Analysis of Procedural Meeting Communication: How Teams Facilitate Their Meetings.” Journal of Applied Communication Research 41, no. 4 (2013): 365–388. https://doi.org/10.1080/00909882.2013.844847

• Presents the idea that good meetings need visible process control: clarifying who will do what, when, and how the group will stay out of dysfunction-swamp.

The Updraft & Kestryl Edge

The Updraft is where I write my personal thoughts and reflections on leadership as I build the company Kestryl Edge. Kestryl Edge is a leadership training company that specializes in teaching emotional intelligence skills to teams working in high consequence technical environments.

We also have writing on our website! There you can read about Burnout, learn about our workshops, and listen to new episodes of our Podcast.

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Grammatical edit made 20260706 AM.

The terrifying part isn’t hanging one-handed from the first bar, or the moment they secure a hold on the next one.

It’s the suspension in mid-air between the two: what was and what will be.

It takes courage to release your grip on the known, with no guarantee of securing a hold on the other side.

In a meeting between Serena and I, we agreed that when it comes to making changes, most organizations design the next bar and pretend the air doesn’t exist.

So it’s not surprising those experiencing change are so reluctant to let go, for fear of plummeting to the ground.

Serena Spink is a former lawyer, corporate leader, and now digital nomad who left a UK FTSE 100 to help professionals develop the leadership skills that are never taught in the workplace, from wherever in the world has good wifi this month.

I’m Dan, founder of Kestryl Edge, a not-your-typical training company that teaches emotional intelligence and leadership skills. ( I always think of Mean Girls, “I’m not a regular mom, I’m a cool mom.”)

Serena and I met, we traded thoughts on change management, and now you get this.

Here’s the deal. We’re each responding to the same three prompts:

1. A change that made you want to change jobs.

2. An energizing change.

3. What we learned, and what you need to know.

Same questions, two very different careers, zero coordination on the answers. You get to spot the pattern yourself.

Enjoy.

A change that made you want to change jobs. (Dan)

I’ve had buckets of change initiatives that failed. I handed off a piece of paper or an idea and just said GO.

I provided the end state, some background knowledge, maybe a ‘why’ as to what we were up to, and then set people loose into the unknown to chart a course and find the grail I told them exists. I failed when I described and didn’t support. I failed when I didn’t collect input and get buy in. And I failed when I treated changes as some instantaneous thing that happens because I gave a speech about it.

I saw this happen in the startup world. We were all given books on Entrepreneurial Operating System (EOS) and were told that this was the new standard for performance, promotion, and organization within the company. EOS is a great template for systems-light teams needing a baseline to grow from. For us, it was a tool to manage and change the workers, but not a tool reciprocally applied to the management.

They didn’t wonder “Am I the right person in the right seat?” “Am I giving my team what they need to complete their goals?” They picked what they wanted from it, what was convenient for them and afforded control and boundaries, and seemed to scrap the rest about leading with EOS. The tools and some jargon stuck around but the culture remained the same. Status Quo unchallenged.

I’ve also seen people come in and announce sweeping changes to work scheduling. Right out of the gates their system received broad criticism, no support from the floor or the leaders who would have to back the change.

The idea was spot on. But the logistics sucked and needed to change.

It’s automation hinged on one person who had written fragile code and when she burned out and left for greener pastures the system fell apart and they had to run it manually.

When people gave feedback and input they shut them down and dis-invited them from meetings.

And the big boss? He didn’t know what was going on or the implications but had made up his mind this change was needed and made his position clear…

get in line or get going to a new job.

We know what happened next. The change was implemented. Everyone hated it. We hemorrhaged people.

And years later the team that’s left is still trying to undo the damage. The original architects long since moved on and are giving presentations about all the successes they’ve had.

All the good they did. It’s one thing to try a change and fail, start again, that’s human. It’s another to make a change, then leave, letting those behind you pick up the pieces.

• Bridges’ Transition Model argues that while external organizational change happens instantly, the internal psychological transition for employees is a gradual, emotional process.

• It requires leaders to first help people let go of the past, actively guide them through a confusing "neutral zone," and finally support them in embracing the new beginning.

A change that made you want to change jobs. (Serena)

In my last company, the organisation decided to introduce a group-wide “talent review” process.

The intention was good. Managers would finally have a structured way to identify their best people, plan for succession, and have the kinds of development conversations that too often got avoided or handled inconsistently. Team members were regularly asking for more help with career development, so it would address a bottom-up request.

What followed was a lesson in how good intentions and poor implementation are not mutually exclusive.

The tools were designed with the managers in mind: guidance documents, frameworks and automated systems. But the people-centred change journey was not.

With very little runway, managers were handed the tools and expected to use them.

Nobody had been clear enough about what they were actually trying to achieve. Nobody had checked whether managers understood the purpose well enough to explain it confidently to their teams - or whether they even believed in it. And nobody had asked whether the tools created would fit into the managers way of working.

The result was predictable. Some managers ran with it. Some ran in the wrong direction. Some didn’t move at all.

The confusion spread downward through the organisation and what had been designed to help people and their career development started to feel, on the ground, like another tick-box exercise that people ‘just had to get on with’.

Something being done to them rather than for them.

After launch, we had to spend significant time and energy trying to course-correct, addressing concerns, clarifying misconceptions, rebuilding trust, while simultaneously needing people to deliver the reviews.

The change wasn’t wrong. The sequencing was.

By skipping the step of bringing people along before asking them to lead others through something new, we didn’t just slow the change down.

We made it harder and less effective for the very people it was designed to help.

• Lewin’s 3-stage model simplifies organizational change by comparing it to reshaping a block of ice through three phases: Unfreezing, Changing, and Refreezing.

• It requires breaking down the status quo to prepare for new behaviors, implementing the actual transition, and then solidifying those new norms into the company culture to prevent regression.

You know the person in the friend group who has great ideas but the follow-through is a little… well… not there?

Send this article to them. Help their great ideas make it out of the group chat through the power of change management done well.

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An energizing change. (Dan)

The best change management I’ve led has all been slow, steady efforts over time to build high performance teams.

No overnight changes. No big speeches or announcements. The change started as observations that a group of people had potential to do better, to be something better.

Nothing happened quickly it was all slow changes over time. Pruning. Planting. Coaching. Pulling strings. Shifting the schedules, roles, and responsibilities just enough that it stuck but not enough that the ripples harmed anyone or distracted from the goals at hand.

Looking at who had untapped potential and giving them the help they needed to become something better the next day.

It’s exhausting.

The easiest thing to do when you have a team that isn’t performing is to turn a blind eye because changing them is harder than getting someone else, your choice performers, to step in. This cheats people of growth though. And good leaders are gardeners of people. I showed up every day. Consistent with my expectations and generous with my support, patient with my explanations, and looking for the best in people. Looking for the delta between where they are and what they could do closing those gaps with a little push in the right direction.

Both times I ensured my desk was as close to the work being done as possible.

Even it means working on the floor itself.

When you’re building trust and saying your priority is the people. You must mean it. Comfy distant offices and calendars full of meetings are moats of comfort for leaders who don’t want to get messy with the reality of coaching people.

My best changes we’re ones where I was slow and steady on the trapeze and I didn’t fear the flight because I trusted my team to grow and I trusted myself to keep showing up.

• Rather than offering a rigid step-by-step roadmap, the Cynefin Framework helps leaders categorize situations into four domains based on their level of predictability.

• Its core contrarian insight is that human organizations are inherently complex, requiring leaders to abandon top-down planning in favor of small, safe-to-fail experiments to discover what actually works.

An energizing change. (Serena)

When I was running the operations for the legal and compliance function at a big UK energy company, we wanted to improve the quality of work across the 200-person department through better behaviours.

We wanted to see more collaboration. More growth mindset. More willingness to think differently and try things that hadn’t been tried before. To really make the improvements stick, we decided it would affect bonuses.

The usual path would have been to cascade it from the top: six of us on the senior leadership team agree the message, announce it to the department, and expect people to fall in line.

We didn’t do that.

Before we said anything to anyone, we sat in a room together and asked ourselves a different set of questions. Not “what do we want people to do?” but “how are people going to feel when we tell them this?”.

We anticipated the pushback. We stress-tested the rationale. We got ourselves genuinely aligned, not just on the what, but on the why, and on the honest answers to the uncomfortable questions we knew were coming.

Then we took those early ideas to the rest of the department managers before anything was finalised. We asked them what they were worried about. What questions they expected from their teams. What felt unclear or unfair. And then we asked for their help in shaping the message.

That last part mattered most.

When you ask someone to help build the thing rather than just implement it, the conversation changes. They stop being a relay station and start being a co-author. They walk into conversations with their teams not just informed, but genuinely bought in.

The change landed. Not without friction, but with far less than it might have had. The middle layer understood the rationale, felt heard in the process, and were equipped to support their teams through it.

• Kotter’s framework is a sequential, leadership-driven roadmap designed to build and maintain massive momentum.

• It starts by establishing a fierce sense of urgency and finishes by permanently anchoring new behaviors into the corporate culture.

Change doesn’t start from nothing. A catalyst is needed. A spark of inspiration. A good idea sent to someone in your circle. Hmmm. If only there was a button you could press to start a change in someone else’s life…

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What we learned, and what you need to know. (Dan)

Leaders need to understand that change isn’t a tsunami that washes away the bad and cleanses the land leaving a fresh picture underneath while management watches on from high ground.

The wave destroys the houses, the trees, the organizational infrastructure. It’s a river that washes and shapes all stones indiscriminately. It carves out the land slowly enough that plants and trees can still take root and be nourished by the change. Not blown over in aggression.

The best changes aren’t sudden, and they don’t happen “because I said so”.

They are intentional, patient, supportive, and reinforcing of humans choosing something better.

Some changes sometimes need to happen fast? Hell yes.

And we can enact change quickly and still not impart fear or resistance. This is where getting buy-in from your leaders becomes important. Herd animals often have a leader and when that one moves, the rest do too. Border Collies herd by finding that one special animal in the flock. Guiding ‘the special one’ to the goal zone will bring everyone else along with it.

Find your cultural leaders, find the person people look to. When they buy in and show a different way, others will follow.

• The ADKAR model says organizations don't change; people change, one person at a time.

• If an individual isn't moving through the transition, the organizational change will ultimately fail.

What I learned, and what you need to know. (Serena)

In my experience, the variable that separates the changes that stick from the ones that quietly collapse is deceptively simple:

Did the people who needed to carry it feel like they were part of it?

Not consulted. Not informed. Part of it.

That requires the people leading change to really understand the people they are asking to change: what motivates them, what worries them and what will make them feel understood.

It means:

• Anticipating what could go wrong and how people will feel best supported

• Finding your influential people early, the people others look to and will follow, and investing in them before you make anything official

• Leaving time to take on board feedback and adapt in response to it

• Being clear and honest about why change is needed, why now and what the benefit is

• Communicating the same message in more ways, for longer than feels necessary, BEFORE anything takes effect

Change rarely fails because the idea was wrong. It fails because the people who needed to carry it were the last to be consulted.

Change works best when it doesn’t feel like something that’s done to you.

Returning to the trapeze analogy, when done well, it makes you want to release your grip and feel safe and supported in your mid-air transition to something better.

The authors

Serena

Ex-corporate leader + lawyer. I left the corporate world to build a different kind of life. Now I help business owners and professionals become confident people leaders. To read more about everyday modern leadership and what it takes to design a career and life that feel like your own.

Read More From Serena

Dan

Do you want to be a better leader and improve the workplace?

Welcome to The Updraft, the wind in your sails for actionable, research-based, punk rock leadership.

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Every group rated me lower than I rated myself.

On every category.

And after several months and 37 essays I am finally ready to write part 5 in my “What the fuck is leadership?” series. The final part. The parts where I commit to what I think a good leader is.

Act 1 - Past

For years, I judged leaders by what I thought great leadership should look like. Then I became one.

In the beginning, I was measuring their merits against the ruler of my books, my knowledge, and what I perceived to be right. My own sense of corporate justice.

The leaders would say or do something and I’d think to myself,

“Well, that’s not what Brene Brown would do”

“Jocko Willink would think differently here.”

And maybe I was right. But I was certainly an armchair quarterback many days. Other days, boots-on-the-ground guy making guesses and gestures at the people above me.

And now I am a leader. I was a leader before. By example. By proxy. A steady force people could lean on and a bridge between perceived chaos and humble execution. A planner, an organizer, and a mover of resources.

We all meet a day where we begin to hold the full responsibility.

The responsibility of

“Where does this person want to go in life?”

“What about this person’s livelihood?”

And, in the extreme cases

“If this person doesn’t make it home, it is on me.”

I lead teams.

I lead a company.

I’ve never had more fun.

I love coaching. Being there for people. Feeling like someone walked into my office with a problem and walked out with an answer, some support, and the knowledge that they could come back if they need.

I love watching people grow. Starting a little lost, tired, bored, burnt out. Nourishing the growth of the person into a version of themselves unhindered, supplied, supported. Ready to go.

Getting work done and feeling good doing it.

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Act 2 - The Dream

I lead the vision for a dream that I hold so dearly I feel like it might crush against my chest from the grasp of my arms and… at the same time, might float away in the wind if I let go for even just a second.

There is no money pressure. There is no deadline. There is no one saying get this done or, else. When you find something that serves your purpose and ignites the fires inside of you, not moving the needle feels like personal betrayal.

This has been the most stressed and tired I have ever been in my life.

Personally, Professionally, Emotionally. I am going through IT. I am, as the kids say, cooked. Maybe chopped? fuck it. Ohio? I’m something and it’s not ‘aura-farming’ or whatever.

There’s that quote running around in my head:

“Isn’t it beautiful to be tired from something you love?”

To which I think…

“Wouldn’t more milk duds and a nap be nice though?”

This past week we completed our first full day pilot of our Leading with an Edge Workshop with an amazing client. 10/10 experience.

We’ve done lots of coaching and other, smaller pilots before but nothing like this with fully polished everything.

Watching your dream come to life before your eyes is so so so satisfying.

There’s something about pouring everything I have into Kestryl Edge and then getting to see it sculpted from seemingly nothing. Magic!

During the workshop we give a module on values. What they are, how we find them, what it looks like to make decisions based off them, how we lead with our values, etc., etc.

And I shared two stories about myself about discovering my values, Grit and Wisdom.

I teared up and nearly fully broke down in front of the workshop attendees because I was sharing some thoughts from inside myself that were so true and raw. I had written these stories late at night, tired, using half my brain to just get things crossed off. And I guess in that half-state I wasn’t self editing. I wasn’t putting my thoughts through the filter of “what is my audience going to think” or even “hmm.. how do these emotions sound out loud?”

So there I am, in front of the room. With no other script to go off, reading aloud the stories about growing up thinking I was unworthy of love unless I worked hard enough I could earn it.

Stories about going home to drink and eat my feelings for letting people walk all over me.

The feeling of hating myself for not being able to stand up for myself in the ways my soul desperately wanted.

Thank god I had a co-facilitator.

The workshop went well. Very well. They learned from us. They laughed. Enjoyed themselves. I learned from them.

And I came away with a sense of self confidence that I think I made the right choice in a business to start.

That was Monday, June 15th.

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Act 3 - My Answer

Wednesday morning, June 17th, I’m opening up my recent 360 review to go over the 15 domains of EQ skills, my personal ranking, and where ~12 of my peers, seniors, and direct reports grade me.

I get feedback all the time. I eat it up. I am coachable and I pride myself on being able to see wisdom. To prune and grow in directions that serve me.

And so when I received my 360 review feedback this week I knew the feedback wasn’t the only reason why I had converged on an answer to “What the fuck is leadership?”

I have been wondering about this for years. And it is cosmic in a way that this week is the week where I feel confident in an answer.

And I scored myself higher than all other respondents on every single item.

The open question feedback was a mixed bag of some really nice compliments, some good assessments of where I am strong and where I can grow. And one person said:

“Anyone lower than him, he asks their opinion. But only asks to make us feel comfortable and does not listen anyway.”

Performative empathy.

Performative.

I’ve talked for hours in workshops and podcasts about the merits of authentic empathy and I have someone in my charge who perceives me to be performative.

Fuck. Me.

reading that I’ve made someone feel not heard makes me feel small

I sat there and thought for a bit. Quiet. Drinking my coffee and hoping with more alertness, I would read the sentence correctly. Disbelief.

Then defensiveness.

“Well, self-report studies aren’t useful anyways and that’s the problem with 360’s is if someone doesn’t take it seriously they just write whatever they want!”

“Wait, can I figure out who wrote that? Then maybe it will make sense.”

Then I began to feel the acknowledgment set in.

The shell feeling of believing you are one thing and being presented evidence to the contrary.

Do I go crawl into a hole and stay there until I forget?

My internal lie is that I am not worthy. I am not enough.

And in making Kestryl Edge my biggest fear is that I am not enough of a leader to be able to ask others to be better themselves.

And in wondering about the journey of leadership and learning all these skills I think are necessary to leadership I think about the oaths of the Knights Radiant from Stormlight Archives, “Journey before destination.”

All leaders who are working on themselves are on a journey. One with no start line. Certainly no finish. And therefore just position and momentum. Like a particle the leader can only be observed where they are or know firmly where they are headed but not both clearly at the same time. Which is unsettling because you don’t get credit for where you’re going.

So here it is. My answer to what a good leader is.

There are leaders who are followable and there are leaders who are worth looking up to.

Good leadership is punk rock.

And the best leaders work on themselves so they can earn the right to ask others to become better.

Leadership is inviting others to greatness and accepting your own invitation first.

The end.

Lina and I both come from the startup world. We were baptized in the chaos of building and trained in the ancient art of wearing every hat at once.

Together, we wrote this piece on what matters most in the startup journey: the interplay between organizational design, emotional intelligence, and the conditions a company needs to thrive.

Lina gets the floor first.

Organizational Design – Lina

Good, emotionally intelligent bosses are great. Nobody really wants to work for somebody they don’t like. But there is something else that’s just as important: organizational design. You see, the research (and, to be honest, my own experience) has shown that companies that don’t implement sound organizational design struggle to retain talent.

And it does make perfect sense.

Having a “bad” boss is not great, we all know that, but while many people experience it as a nuisance they bond with their colleagues over, it’s usually the culture and system that eventually wear them down.

Employee #3. A Dream Job. But Sadly, Not Forever.

Several years ago, I joined a small company (as an employee #3!) where my job description was more suggestion intentionally crafted role. Believe it or not, I enjoyed it greatly. In fact, I enjoyed it so much that I’d boast to all my friends about how great I had it.

I was growing and learning at a tremendous speed, picking up skills I hadn’t even planned to even learn, figuring things out in real time, and building things from scratch. Badly at first, of course, but it was a school I didn’t know I wanted. I also had the opportunity to be involved in nearly all areas of the business and figure out what I liked and didn’t like in each of them. To sum up, I was getting paid to do work I enjoyed and learn new things along the way. It felt more like a dream than a job.

The company culture itself was questionable, however. And I didn’t necessarily see eye to eye with my boss (and that mattered to me), but I enjoyed the role itself so much that I ignored everything else.

Of course I did. We can’t have it all, after all.

The company eventually grew. More people joined, roles became more specific, and mine narrowed. At first, I felt relieved. I had been overworked, worked overtime regularly, and often couldn’t find time to eat, so having a clearer scope and people taking over parts of my work felt like a gift.

But what happened later was something I couldn’t have expected.

Because I had been there the longest, I became the person responsible for the critical things only I knew how to do. So over time, my role shifted into something where I was doing the most valuable work for the company, and the least interesting work for me.

I was spending most of my time updating spreadsheets, managing logistics, and tracking expenses. And, listen, I’m not a spreadsheet girlie. I started as a creative marketer – I loved nice pictures and engaging words.

We had conversations. We looked for ways to fix it. But I eventually accepted that there was no way forward. I no longer enjoyed my job or found meaning in it, and the culture and systems of the organization itself had become much more prominent in my experience.

So I started to feel stuck. My motivation and engagement hit rock bottom. I tried everything to stay motivated. And every single morning I’d manage it, right up until I walked through the door. Every time.

But the thing is, I had some shares I could’ve exercised if the company exited. The team was working hard toward that.

I wanted them.

But apparently not enough.

After a long time of deliberation, I quit.

And said goodbye to the shares that may or may not have been worth something in the future.

The Part I Only Figured Out After I Left

Here’s the thing I realized afterward, though. It wasn’t my boss that was the main character in this story.

My role was the painkiller. While it was working, I couldn’t feel anything else. But when it stopped fitting me, everything I’d been ignoring suddenly came into focus, the culture, the way decisions got made, what got rewarded, who got developed, how communication happened, what was prioritized. The whole room, basically.

And I realized I didn’t really vibe with any of it.

I’d hear my friends talking about their workplaces and how well their companies took care of them. And I was jealous.

There’s a name for what happened to me. Hackman and Oldham’s Job Characteristics Model says five things make people like their work: doing different kinds of things, seeing how your piece fits the whole, knowing it matters, having some say in how you do it, and knowing how you’re actually doing (Hackman, 1976).

Strip enough of them away and the work stops feeling meaningful, regardless of how much you loved it before.

The startup phase accidentally gave me all of them. The growth phase accidentally took most of them away. And once they were gone, I suddenly started to care about everything else.

Here’s what I now understand about organizations: it’s never just one thing – a role, a boss, a salary, or whatever.

When I look back at that startup, what I actually see is a whole system that nobody designed properly.

Galbraith had a model for this kind of thing - five elements that need to work together, and in my old company, I don’t think most of them did. Strategy that shifted before everyone got clarity on the previous one. A structure where the org chart and the actual power had nothing to do with each other. Decisions that happened to you rather than with you. Rewards that celebrated the wrong things. Growth that meant surviving the next sprint, not becoming better at your job.

All of it together creates the work culture. And once I could see it, I couldn’t un-see it.

That’s just how most startups are built - in a hurry, on instinct, with good intentions and no time to think.

But intentional org design doesn’t require a big company or a fancy consultant - it just requires someone who wants to make things work well together for the people inside it.

The Burning Room

Low emotional intelligence makes people not want to work for you in the first place (and makes sure they tell everyone about it when they leave).

But lousy organizational design does something more damaging: it loses the people who’d otherwise wanted to stay.

Emotionally intelligent leaders are more likely to notice when their design is failing their people and do something about it. They may not be equally important in theory, but without intentional org design, even the warmest, most likeable leader is just holding a good conversation in a burning room that nobody wants to be in.

Emotional intelligence - Dan

Technical intelligence can invent. Unreasonable people can dream. Emotional intelligence gets other people to build, buy, trust, endure, and believe, carrying the dream into reality.

Credentials ain’t it.

Startups fail when we mistake credentials for leadership capacity.

I live in Los Alamos, New Mexico, a town with the highest concentration of PhDs per capita.

When I started coaching CrossFit on the side, I began to learn the community and found out quickly where I was. A deadlift diagram I drew to explain core bracing turned into a heated discussion about moment arms, height disadvantages, and the force required per inch of athlete to lift the same weight.

I shit you not, someone pulled out a graphing calculator during my warm-up brief.

Step aside, gym bros. The engineers are talking, and their force calculations do not care about your partial reps.

Around here, you hear particle physics in the grocery store. You see chemical structure tattoos. NASA mission bumper stickers. The air itself smells like peer review and impact factor.

I share this because I want you to understand the water I swim in. I know what it feels like to be surrounded by people who are much more formally educated than I am.

And after five+ years of coaching, I’ve learned something startup culture still gets wrong: education and character are not the same thing.

The most credentialed people are not always the easiest to teach. They are not always the quickest to listen. They are not always the ones who show up, take feedback, adjust, and do the work.

Sometimes they are.

Often, they are not.

That matters because startup culture worships credentials. Founders often have graduate degrees. C-suites are full of them. And to be clear, a graduate degree is not nothing. It means you survived a difficult intellectual gauntlet. It means you developed advanced skills.

In my case, it means I know a thing or two about nanoparticles and can build one hell of a spreadsheet.

It does not mean I know how to hire, coach, give a performance review, repair trust, sell a vision, or lead people through uncertainty.

Giving a chalk talk is not founder sales.

Writing a research report is not a pilot proposal.

Technical skill overlaps with leadership, but the overlap is small.

Very small.

This is not an argument against education. It is an argument against confusing education with leadership.

You can be smart. Really smart. Fabricate-a-durable-solar-cell-from-trash-in-your-microwave smart.

But if you are a prick, if you cannot read the room, if you cannot bring people with you into the future, no one will follow you for long.

A room full of brilliant people does not automatically become a brilliant team. Woolley and colleagues found that group performance was not simply explained by the summed intelligence of individual members, but was more strongly linked to social sensitivity and inclusive participation in conversation (Woolley et al., 2010).

That is the thing emotional intelligence makes possible: who notices tension, who makes space, who can read what is happening before it becomes a fire.

That invisible field matters. Psychological safety is linked across teams to stronger learning, performance, information sharing, and engagement outcomes (Frazier et al., 2017).

That matters even more in startups, where ideas, hopes, and dreams are the product before the product is the product. Research on new venture teams found that ‘shared leadership’ predicted startup performance, including revenue and employee growth, which means companies scale when leadership moves through the team (Ensley et al., 2006).

Cults.

Startups are cult-like by nature.

Not always in the sinister way. But structurally? Absolutely.

Startups have origin myths. Sacred language. Rituals. Heroes. Enemies. A promised future. A tiny group of believers trying to convince the rest of the world that reality is about to change.

It’s part and parcel of their power to disrupt.

You almost have to build a belief system before you build a company, because in the beginning there is not much else to hold onto. There is no massive customer base. No stable process. No guarantee the thing will work. Often, no thing itself.

There is just a room full of people staring at uncertainty and deciding, together, not to blink.

And belief is dangerous.

The same force that helps a team endure can also be used to excuse harm. The mission becomes a muzzle. Loyalty begets silence. Sacrifice becomes exploitation. The founder’s vision can become a fog machine that hides the fact that people are exhausted, afraid, or being asked to confuse abuse with commitment.

Emotional intelligence is the discipline of noticing what your belief system is doing to the people inside it. It is knowing when conviction has become coercion. When urgency turns into panic.

When standards become humiliation. When loyalty has become fear.

Because a startup needs belief.

Belief without emotional intelligence becomes a cult.

Belief with emotional intelligence becomes culture.

Not a soft skill.

Emotional intelligence creates the psychological safety that lets people tell the truth, challenge

bad assumptions, admit mistakes, and keep moving when the work gets ugly.

It is not the bedrock

or the foundation

or the pillars

or even the allegorical roof.

It is motherfucking gravity.

It is the invisible force that holds people together when life sucks. It is how you know you said the wrong thing. It is how you show up when things are unorganized, uncertain, and you are stressed to your wits’ end.

It is not a soft skill.

It is the hardest skill there is.

And for whatever asinine reason, most colleges do not teach it.

That is why startup culture keeps flattering technical founders into confusing brilliance with leadership. They were trained to think.

Not to lead.

You have to be unreasonable to build something new. A little delusional, too. Different is beautiful. Different is how we see futures other people have not made room for yet. But big dreams do not move by themselves. You cannot manifest them alone. You need allies.

You need people willing to lend their time, talent, reputations, and nervous systems to a future that does not exist yet. That is the founder’s real job.

Converting uncertainty into conviction. Fear into action. Conflict into collaboration. Talent into momentum. A private dream into a shared reality.

And that is why emotional intelligence is gravity.

You do not always see it, but you know when it is gone.

The room starts floating apart. The smartest people stop telling the truth. The quiet people

disappear first. Bad ideas survive because challenging them feels unsafe. The mission gets

louder and the culture gets weaker.

Brilliant ideas die when people stop believing, stop trusting, and stop following.

The best ideas do not carry companies.

People carry companies.

And emotional intelligence is what keeps them from letting go.

Authors

Lina

Lina spent 12 years inside startups and small companies. Now she helps founders fix messy, unclear ways of working by designing human-centred systems where people can do their best work and not lose themselves in the process.

Learn more from Lina

Dan

Dan writes The Updraft, a publication on management science for leaders in high-reliability environments. Chemist. Ultra-marathoner. Founder @ Kestryl Edge, LLC.

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References

Galbraith, Jay R. Designing Organizations: An Executive Briefing on Strategy, Structure, and Process. San Francisco: Jossey-Bass, 1995.

Hackman, J. Richard, and Greg R. Oldham. “Motivation through the Design of Work: Test of a Theory.” Organizational Behavior and Human Performance 16, no. 2 (1976): 250–279. https://doi.org/10.1016/0030-5073(76)90016-7.

Ensley, Michael D., Keith M. Hmieleski, and Craig L. Pearce. “The Importance of Vertical and Shared Leadership within New Venture Top Management Teams: Implications for the Performance of Startups.” The Leadership Quarterly 17, no. 3 (2006): 217–231. https://doi.org/10.1016/j.leaqua.2006.02.002.

Frazier, M. Lance, Stav Fainshmidt, Ryan L. Klinger, Amir Pezeshkan, and Veselina Vracheva. “Psychological Safety: A Meta-Analytic Review and Extension.” Personnel Psychology 70, no. 1 (2017): 113–165. https://doi.org/10.1111/peps.12183.

Woolley, Anita Williams, Christopher F. Chabris, Alex Pentland, Nada Hashmi, and Thomas W. Malone. “Evidence for a Collective Intelligence Factor in the Performance of Human Groups.” Science 330, no. 6004 (2010): 686–688. https://doi.org/10.1126/science.1193147.

(small grammar update 6/17/2026)

The Updraft is a leadership page and a profound leadership journey for me has been learning to be an older sibling. I’m not done with this journey. And it’s hard to say if I land closer to beginning or ending. All I know is I’m on the journey.

As the oldest brother you’re the first male trial run. You blaze the trail. Lessons are learned the hard way. And if you do your job right he sees you winning or fucking up and course corrects.

You hope to protect him from things going wrong. I don’t think I always did a good job of this. Being four years apart he lived a distinct life from me in school. We only ever had one year of overlap and that was one of my favorites. He was a freshman in college and I was starting grad school. He’d come over about once a week and I would make dinner while he studied. There’s something about knowing the answer to a chemistry problem and cooking a steak for someone who’s only getting dorm food that made me feel like a super hero.

It’s those moments I felt like a provider.

He is the best at making friends I’ve ever seen. I surprised him in college for his 21 run and I was met with a platoon of over 50 of his friends following him around. A entourage of epic proportions.

At one point I turn around and he’s got $40 in his hand and is wearing a completely different shirt. I didn’t even see it happen. I asked him about it and he said the woman at the bar just bought his shirt from him and gave him hers.

He explained this to me like it was obvious. Like this is a natural consequence of being out on the town. Like someone would explain the weather that day.

Even if you think you know everything, like you’re the veteran guide… he still has a way of educating you how life works. And sometimes the lesson is that the barkeep will buy your shirt off your back.

He still looked great.

As the older one you know a little more slang, you’ve seen a few more movies, and you’re a little bigger. So you’re in prime position to talk smack, rough house, and come out on top. I know I took it too far sometimes. I don’t think I’ll ever forget those moments where your stomach drops because you played too rough, did something stupid, and ended up hurting your little brother.

The sticks thrown in the spokes of your bike. The teasing about your personal life. Getting in arguments about small stupid shit. The setting up an automation so for several years in a row you got a text from me at the same time every day saying “Hey, what’s up?”

And so now that I’m a little older and not throwing sticks or automating maliciously, I strive to be the world’s best hot line.

He calls, I pick up the phone. For the short calls, the medium calls, and the calls where the world is caving in and I pull up a white board to diagram the epic shit we need to strategize our way out of.

I remember you becoming captain of the rowing team and hearing how you were going through hard times as a leader at the top. You were realizing how lonely it is up there. How, as a leader you’re pottery on a pedestal, and it’s easy for people to see the cracks.

The post break up calls. The ‘I just moved somewhere new and need a friend’ calls. And the ‘oh shit I just fucked up what am I going to do’ calls.

I cherish them all.

If you’ve never been an older brother, imagine someone who looks kind of like you, but is better at most everything... and better looking. Then imagine sometimes you get to be there for them and those moments make you feel like the coolest person alive. That’s a start to what it’s like. It’s not all of it though.

My younger brother had a birthday recently. He just passed some final exams and is now officially a dentist. The second Doctor among my siblings. As the middle child I get to travel the non-traditional path. And from this non-traditional path of mine I get the pleasure of writing about how much I love them and look up to them.

He’s not out of school yet, and he already has stories of fighting for the care and well-being of the homeless and unwell. People who need help and don’t have a single person in their corner fighting for their wellness.

He has some amazing stories of fearlessly standing up to administrators, mentors, colleagues, and peers.

Saying “I don’t need you all to agree with me - this person needs help. And I’m going to be the one to help them.” Badass.

He is succeeding in leveraging the system to get help to people who are in need.

I couldn’t be more proud of him.

So he asked for some advice for his birthday and here it is.

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My little brother,

Whatever you do, don’t stop.

You’re on the right path. Your gut is calibrated for kindness and resilience. As long as you don’t stop, the world will be a better place every time you step into motion.
Momentum changes paradigms and keeps us moving along when we need to catch our breath.
As long as you keep going, you can’t lose.
So whatever you do, don’t stop.

Learn how to say no

Once you know what you want, you should say no to everything that’s not exactly what you’re after.
Compromising on your dreams, wants, ambitions, journey,..., it takes something from you.

If you want something don’t let other people get in your way or tell you you can’t do it.

There’s only two things you need to do to get something you’re after

1. work your ass off

2. build habits that allow you to work your ass off better.

Learning to go to bed by 9pm. Learning to be up at 5am, just like during rowing.
The morning isn’t just for intense cardio with the team, it’s for the doers, it’s the best thinking of the day, it’s the audiobook time, the run, the stretch, the balanced breakfast and ironed shirt, the reviewing the meeting brief before you even get to work, for getting ahead before most people open their eyes.

The habit we all need is the habit of saying no. Of staying focused. Of picking a boring day that serves the dream instead of an interesting one that doesn’t move the needle.

You’ve clearly mastered this. Look at your work in dental school. Once you’re out and ready for more. Remember those days and find them again once you’re ready to chase another dream.

Say no to mystery drugs. Powders ain’t what they used to be. If you can’t test them, play it safe.

Start reading books on communication and leadership

Emotional intelligence, negotiation, and leadership are arts. Yes, they have very real and practical tools and skills. But the combination and application of those tools and skills comes down to you as a person and how you paint with words.

You have the biggest heart I know of. Emotional intelligence sharpens this and turns it into super powers. Wisdom and then influence are seeded here.

Find a community and invest in it

Community used to be the neighborhood, the church group, the family living next-door.

We’re spread out now. You and I are states away. Community is important because life won’t always go as planned and your community are the people you can lean on when you need some help. They are the wind in your sails when you try something new. The people who root for you when you’re down and out but working to get up.

You are an incredibly capable person and you have things to offer. Being there for other people is the highest calling. As a dentist you will give, and give, and give. Give more than you get and find some people who you can invest in and who can give back.

w/ love, Dan.

The Pond

The worst I’ve ever been mad at you was two thanksgivings ago. I was stressed. You were too. That was one of the worst weeks for us, probably ever.

A thanksgiving after bringing dad home from the hospital from a near-fatal heart attack is a fucked up week for many.

It was a wake up call to the mortality of our parents. The illusion of immortality broken in less than 24 hours. The realization that they may not always be there.

It was cold. Snowy.

I never sleep well away from Cara or the dogs. I was stressed. You were going through it. And I was pissed beyond belief. The uncertainty and exhaustion had gotten to me. I knew we needed to try and patch things up before parting ways, though.

And the night before I went home I said we needed to go for a walk. The walk ended up lasting hours. Four or more, I think.

We had big puffy jackets, a bottle of white wine, our fear and anger, and the dim street lamps of our familiar home streets.

I spent the first bit venting at you. You listened.
Then, you told me how you felt. And I listened.

There’s a special gut punch when you hear how someone you love feels and all your anger and frustration melts away as you see behind the curtain of your own assumptions to realize all the fucked up shit they’re going through.

So I listened more.

And then we started asking questions. Walking from park bench to park bench as we unpacked the entire week. We unpacked the past few years. We unpacked our relationship and family in ways only possible at 1:12 AM in an abandoned park in winter.

Our last park bench of the night was infront of the duck pond.

I feel like I knew you growing up. That night, in front of the pond, I was getting to know the you - you chose to be, not the you - you were.

When the wine bottle was empty and you said we should jump in I knew I would regret it for the rest of my life it I didn’t.

Duck shit be damned. I wasn’t going to be a coward. Older brothers aren’t cowards.

And so we stripped. Baptized ourselves in the frigid waters of the duck pond.

And scurried home wet and mostly clothed.

Warm showers, warmed-up thanksgiving leftovers, and a good bye before bed and we were whole once again. This time more whole than before.

When pottery is on display it’s easy to see the cracks. Imperfections make us real. And cracks show us what the art has survived. What it’s gone through to show us it’s beauty.

Patrick, I’m proud of you. And I love you.

-Dan

P.S. I remember the man dressed in all black we kept seeing that night. Crossing the path in front of us. Walking into thickets and patches of trees. Out of sight.

As an older brother I have to keep my cool. Be the one to not freak out. And I wonder if that man was real.

(minor grammar edit 6/16/2026)

A helpful manager’s presence is a scarce resource.

If you spend it sitting silently in low-value meetings, you are not “staying aligned.” You are taking your judgment, problem-solving, decision-making, and emotional-regulation meat suit away from the people who are your primary responsibility and who actually need it.

Welcome back folks to Dan’s hot takes. In this essay I will be roasting all managers who go to all the meetings they are invited to.

If that’s you… know that I understand performative meeting culture is not entirely your fault. Most organizations reward calendar gravity and call it leadership. I understand how good it feels to be needed and to go to meetings and feel like you’re having an impact.

This essay is for you. I hope it finds you. It’s also for the managers who go to lots of meetings and don’t know how to feel about it yet.

Before the color coded agenda people start lighting torches: yes, some meetings matter. We’ll get there.

I waste a lot of time in meetings. You waste a lot of time in meetings. We all waste a phenomenal amount of time in meetings.

And most meetings don’t do shit for your team.

Your actual job.

As a manager, you’re a leader who’s responsible for discrete business outcomes. Actual work. Things getting better, safer, faster, easier, more done, less on fire.

You have resources. A team, cash money budget, and time. Your job is to leverage those resources to orchestrate value for the customer and/or the organization.

You also have some innate responsibilities that come with the role of having people in your charge:

1. Keep your people safe physically and psychologically.

2. Solve the problems your team cannot solve yet.

3. Pull resources from the organization to keep your team properly leveraged.

4. Stay emotionally regulated when work starts turning into a fiery raccoon tornado.

Okay so there’s your job description. In a sentence?

Be there for your folks and get work done.

Meetings aren’t in your job description

There is nothing in there about going to meetings.

In fact, going to meetings makes you worse at getting your job done.

• You’re not in your office available for your team.

• You’re not on the floor staying aware of what’s going on.

• Problems have to wait for you to be available.

• People aren’t able to go to you when they need you.

• You’re slow to respond during emergencies.

So why go? Optics? Is your big ol’ boss expecting you there? Do you think that meeting that you didn’t prepare anything for and you’re just going to be a warm body in, where you’re expected not to raise objections, is advancing the institutional goals and objectives?

AAAAaaaaaa. False, my homie.

Your team does not experience your full calendar as leadership. They experience it as latency.

If you were available for them when they needed you and you got their problems solved and their needs met as soon as they had them, you would be their superhero.

This. Is management.

Management isn’t being in meetings.

Management is being a lethal weapon problem solver extraordinaire who gets mega shit done and teaches their team to do the same.

Every meeting attended has an opportunity cost. The cost is not just your time. The cost is your team’s access to you.

Now,

If you share my leadership philosophy, your purpose as a leader is…

to not be needed.

Meetings are side-quest generation machines.

Going to meetings gets you work assignments that don’t benefit your people.

I’m not saying don’t be a team player, but you should have a boundary on what you take on and don’t because your #1 priority is the safety and wellbeing of your squad.

Period.

Side quests are for the backlog, and we hire people to go do those, not our highly trained managers who are supposed to be investing in their squad.

The Leadership Management Paradox

You’re saying I’m needed and I’m not there but my goal is to not be needed…. So… WTF Dan, how are both true?

Well,

It takes time and intentional training of your people to not be needed.

And 97.3% of teams aren’t there yet. And when they are, we promote, disperse our talent, and get new folks. This work is never done when you do it right.

When we put the two together, be there and not be needed, you’re not freeing your calendar because you’re going to solve all your team’s problems for them like a babysitter.

You’re becoming available to support and mentor your team so they can grow as individuals and solve problems for themselves without you.

So if/when you’re not around, they execute at the highest level.

The Challenge

If you’re sitting there thinking, “Well Daniel… I HAVE to go to all these meetings. And you just don’t get it. And my team is great and I didn’t have to train them. They just don’t need me.”

Yeah… sure buddy. Let’s try something together.

For one week, skip, delegate, shorten, or ask for notes from every meeting that does not need you for a decision, blocker, risk, relationship, or representation function.

Then spend the recovered time on the floor, in your team’s work, removing blockers, coaching people, and finding the problems that have been waiting for you to be available.

If your team comes back after that week and says, in writing, “This provided no value and did not help us get closer to our deliverables,” I will personally Venmo you $100 and write an apology blog saying I was wrong and I’m a big dumb idiot.

Go ahead. Try it. Try one full week of fewer meetings and more direct team support.

One other small point real quick:

A helpful manager’s presence is a scarce resource. If you spend it sitting silently in low-value meetings, you are stealing it from your team.

Practical Better Awesomer Options For UnFu*king Your Calendar

The goal is not to never attend meetings. The goal is to stop donating your presence to rooms where you are not meaningfully changing important business outcomes.

Send someone on your team.

This is called delegation. Sound it out with me: Del-E-Gat-Ion.

Why it works: The person closest to the work has better answers than you do. They will learn more from being in the room than you will.

How to do it: teach them how to take notes, make quick decisions inside a defined boundary, and bring back the three things you actually need to know.

Never have two leaders from the same team in the same meeting.

If you’re all in the same place at the same time, you’re wasting your time. If I walk into a meeting and see my boss or my colleague there, I ask them if they’re good, then leave.

Why it Works: Distributing your span of influence allows you to be there for your people AND have leadership presence in the meeting. By taking turns you’re cutting down the bullshit by however many managers are in your leadership rotation.

How to do it: One a month review your calendars and ensure you’re covering your bases. Make rules on who goes to what. Stick to those rules. Then if you walk into a meeting and one of your team is there. Figure out in 20 seconds who needs to be there and then stay/leave.

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No Agendy No Attendy.

I don’t go to meetings that don’t have agendas. They are typically unstructured and inefficient.

Why it works: If I don’t know what it’s for and why I need to be there, I’m just going for the fun of it and that’s a useless waste of time.

How to do it: It is not rude to send a 2-minute email to someone asking, “Hey, I saw this meeting and want to know what it’s about so I can prioritize being there if you need me in particular. I’ll take a rough agenda if you have it.”

You aren’t being a pain in the ass, you’re cross-coaching for organizational results and efficiency.

You’re cross-coaching others to become better leaders.

Block out your deep work and your manager floor time.

Block out a few hours every day for you to get your work done. No scheduling over that time unless it’s an emergency.

Why it works: Guess what!? You’re not the most important person in the office. And when you decline, they will probably have the meeting without you and be just fine. You are not needed there. But your people DO need you.

How to do it:

1. Block out your floor walks. It’s a meeting just for you.

2. Block out your office hours. Interruptible deep work.

3. Decline everything that gets scheduled over those times. And watch the magic happen.

Some meetings are valuable, necessary, and worth your time.

Go when you are needed for a decision, a blocker, a risk, a relationship, or a strong representation function.

Why it works: This will help you keep your job.

How to do it: When do meet, be the best. Agenda - on lock. Key stakeholders - locked in.

The how to is in a separate essay where I provided some absolutely bangin’ tips on how to make your meetings more productive.

Want to control meeting outcomes? Want to be the top G in meetings?

You’re one click away from my advanced bloodline technique meeting jutsu of professional success. Domain expansion: corporate excellence.

If anyone gets upset with you send them this article and tell them Dan wanted to have a word. I will back you up 1000% percent. Just like,… a good manager would. See what I did there?

Have a great week,

-Dan

References

(reach out if you have questions about these)

Barends, Eric, et al. Productive Meetings: An Evidence Review. London: Chartered Institute of Personnel and Development, 2023.

Deci, Edward L., Anja H. Olafsen, and Richard M. Ryan. “Self-Determination Theory in Work Organizations: The State of a Science.” Annual Review of Organizational Psychology and Organizational Behavior 4 (2017): 19-43.

Drucker, Peter F. The Effective Executive. New York: Harper & Row, 1967.

Edmondson, Amy C. “Psychological Safety and Learning Behavior in Work Teams.” Administrative Science Quarterly 44, no. 2 (1999): 350-383.

Hackman, J. Richard. Leading Teams: Setting the Stage for Great Performances. Boston: Harvard Business School Press, 2002.

Lehmann-Willenbrock, Nale, Steven G. Rogelberg, Joseph A. Allen, and John E. Kello. “The Critical Importance of Meetings to Leader and Organizational Success: Evidence-Based Insights and Implications for Key Stakeholders.” Organizational Dynamics 47, no. 1 (2018): 32-36.

Rogelberg, Steven G., Joseph A. Allen, Patrick Shanock, Cliff Scott, and Marissa Shuffler. “Employee Satisfaction with Meetings: A Contemporary Facet of Job Satisfaction.” Human Resource Management 49, no. 2 (2010): 149-172.

🥳 This guy. 🥳

Despite that, today I hit 100 subscribers. Pretty special moment.

A tiny milestone in internet terms. A massive milestone in Dan-terms.

The Story

January of this year, I started a company.

A podcast, a curriculum, a website, a mountain of systems and processes, and six contractors.

And approximately seventeen thousand things neither of us had ever done before.

A few weeks before we start the podcast I confess to my new co founder, my co conspirator, my co maniac, that I was scared to be in front of the camera.

I was scared to share my thoughts.

And believe me, I am still frightened.

I’m scared that one day, the imaginary haters in my mind are going to find my work and expose me for somehow being a fraud, or an ass-hat, or both.

That all the shadows in my closet are going to pop out and yell:

“Gotcha bitch!”

So anyways I have a mini-meltdown like a totally EQ conscious boy boss.

February 18 of this year I posted my very first shitty Substack article.

5 likes. Ta-Da! Not a humble brag. One like was me and the rest were family and friends I bullied into liking it. It’s manufactured vanity metrics.

I haven’t stopped yet. These past few months have been me writing my real-Dan-thoughts as fast as possible before I can think twice about it.

Holding my breath and waiting for the other shoe to drop.

And that shoe is not dropping.

And I have ✨anxiety✨

In Avengers (2012) The Hulk says:

“That’s my secret Cap… I’m always angry”

Well, my secret is:

“My tummy is distressed and I’ve already imagined seven different disasters.”

Anyways.

Thank you. A genuine, real, bona fide, thank you.

We’re all walking around carrying ideas we hope matter.

Know that by reading, sharing, and encouraging me, you’re pouring gas in my dumpster fire of dreams and passion.

Remember: you chose to sign up. I have personally contacted Chris Best, CEO of Substack, and deactivated my unsubscribe button for The Updraft.

To my haters who are in the shadows, plotting revenge against me and my micro brand:

Please get in touch.

I think you’d make a fantastic podcast guest.

w/ love and some pocket Tums

- Dan

The Data for My Nerds Out There

Gather round, fellow graph goblins. 👺

I’m strong in the PNW (minus Idaho but some people don’t count Idaho), the south west, the mid west, and the east coast has not caught on yet!

The places with Dan-representation:

1. The best National parks

2. Places with great coffee

3. Strong overlap with most cryptid and big-foot sighting locations.

I would like one subscriber from every state. That’s my new side quest.

Summary

Danielle sits down with Dan, co founder of Kestryl Edge, for a wide-ranging conversation on emotional intelligence in the workplace. They cover why EQ is not a soft skill, what leaders get wrong about training their teams, how values become a decision-making compass, and what advice they'd give to people at every stage of their career, from first-day employees to C-suite executives. Raw, practical, and zero PowerPoints.

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Quotes from the episode

“We don’t want people’s ideas and dreams failing because they can’t work with people.” — Dan Korus

“Leadership is not a one-and-done training. They remember about 10% of what they learned — and while they’re in that training, they’re worried about the emails piling up.” — Danielle Shroyer

“People tell me you can’t teach emotional intelligence. I fundamentally disagree. It’s just like lifting weights — it’s time and reps. Our job is to show people what the gym looks like.” — Dan Korus

“We call them soft skills. They’re hard skills. They’re very trainable in the same way any hard skill is trained.” — Dan Korus

“Values aren’t always something that we are. They’re also something that we aspire to be. They’re our compass.” — Dan Korus

“When you make decisions that are consistently in line with your values, the trust with the people around you really starts to accelerate.” — Dan Korus

“The leader controls what’s said, whether they mean to or not.” — Danielle Shroyer

“Culture is created by leaders. If you don’t recognize that you have leadership issues — or you recognize it and don’t do anything about it — that’s a problem.” — Danielle Shroyer

“HR carries a lot. Promotions, new babies, cancer diagnoses, bereavement leave. And they can’t talk about any of it.” — Danielle Shroyer

“I rearranged the entire lab on my first day. Total power move. They hated it. My system made sense though — I’ll hold my guns on that.” — Dan Korus

A real pleasure being invited to your live, Danielle.

Cheers,

Dan

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