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How to Lead With the Plan: Charles Conn

How to Lead With the Plan: Charles Conn

Update: 2025-12-31
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Here are three provocative questions that arise from this Change Signal conversation with Charles Conn:




  •  What’s the smallest experiment you can start today?




  •  Where can you loosen control without losing direction?




  •  And could your team learn faster if you planned less?




Charles Conn — investor, conservationist, and author of The Imperfect Leader — joins me to talk about how great change leaders stop waiting for perfect clarity and start moving through curiosity. He argues that big “master plans” have had their day. Progress now comes from small, reversible bets, the kind you can learn from quickly and cheaply.


We explore why senior leaders should push more decisions to the edges, how to create trust inside small, cross-functional pods, and why imperfectionism is the essential mindset for real transformation.


If you’re steering large change projects or guiding cultural shifts, this episode is a practical invitation to trade certainty for learning — and to rediscover the messy, energizing craft of strategy that actually works in complex systems.


Change Signal. Cut through the blather, the BS, and the noise to find the good stuff that works in change. If you’re a transformational leader seeking modern change mastery, you’re in exactly the right place.


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How to Lead With the Plan: Charles Conn

How to Lead With the Plan: Charles Conn

Michael Bungay Stanier