#302: Coaching Session: Overcoming My Delegation Problems with Michael Bungay Stanier

April 21, 2026 · 1 h 7 min

Show notes

This episode is a little different. Michael Bungay Stanier, author of The Coaching Habit, with over a million copies sold, reached out and offered to do something I didn't expect: a live coaching session, recorded, here on the podcast. The topic: my delegation issue. Not the tactics (I know the tactics). Something deeper has its foot on the brake.

What unfolded was one of the most honest, vulnerable conversations I've had on this show. Michael walked me through the Immunity to Change framework, where we uncovered that I'm getting more out of the status quo than I realize. There are commitments I have to the way things are right now that I haven't even named. We named them. And then we ran small experiments to test whether the things I'm most afraid of would actually come true.

Full transcript and show notes

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TIMESTAMPS

(00:00) The inner monologue: lack of courage

(00:22) Introducing Michael Bungay Stanier — and why this episode is different

(01:46) Michael's outreach: 'Your delegation issue is probably hard change, not easy change'

(03:24) The setup: Jay's wife is the only other 'full time employee'

(08:58) Easy change vs. hard change — and why more tactics won't solve hard change

(14:24) Defining the real challenge: more time on the business, not in it

(17:26) The embarrassing list: all the things Jay is doing (and not doing) contrary to his goal

(22:48) Flipping the script: what would you be worried about if you actually delegated?

(26:30) Competing commitments — the foot on the brake even while pumping the accelerator