Twenty-four hours before this recording, I taught a workshop module on performative empathy. I got my 360 review results the next morning. One comment: Dan only listens to me because he thinks it’ll make me trust him. I never see him do anything with what I tell him.
So!… that’s the episode.
I brought that exact moment to Rich Reynolds, a licensed marriage and family therapist who made the jump into leadership coaching, and asked him to coach me through it live. No prep, no script, just the actual discomfort.
What came out of it is a framework I haven’t stopped thinking about since. Rich’s core claim: the reason you struggle in a leadership role is the same reason you’d struggle in a marriage or with an addiction. Same emotional process, different context. Somewhere back in childhood you built a set of strategies to get your needs met when the adults around you couldn’t fully meet them. Those strategies work. They get you promoted, they get you married, they get you through your twenties. And then they hit a ceiling. He calls it stage one and stage two, and most of us are still running stage one code in a stage two job.
We also get into the thing nobody teaches you: how to be angry at work without either torching the relationship or swallowing it and calling it professionalism. Rich walks me through what he calls the middle ground, full eye contact, full presence, zero aggression, and I watch myself get genuinely heated mid-conversation talking about a manager who lied to my face to get at one of my team members. It’s not a polished moment. That’s kind of the point.
If you’ve ever caught yourself performing the empathetic leader instead of being one, or you’ve got a boundary you keep meaning to set and keep not setting, this one’s for you.
Rich writes The Self Reflective Leader here on Substack.
The Updraft is research, field notes, and conversations about the parts of leadership no tool can practice for us. Changing the system from within.
I’m Dan Korus, founder of Kestryl Edge. I spent years learning leadership the hard way: burnout, toxic bosses, and the Peter Principle.
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