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The Right Questions

“The important and difficult job is never to find the right answer; it is to find the right question.” – Peter Drucker

We’ve been sitting on a new series of mini-casts for the Reboot Podcast channel since this summer. My goal was to bottle up some of Jerry’s thoughts about the more practical side of leading and building organizations. Practical Skills is part of our formula, after all (right next to Radical Self-Inquiry).  

In working with my CEO clients and tracking CEOs that have come to our bootcamps over the years, common questions pop up. Among them are what seems like a basic one: What is my job as CEO? Sometimes the question is: What is my job as CEO, now, at this stage of the organization? It’s a role that, when played well, shifts and scales as the company grows and develops. 

One of the consistent requirements of the job, though, is a keen awareness of the nuances of leading people. This requires human relating skills like listening, asking open honest questions, learning the stance of ‘leader as coach’, receiving feedback without knee jerk reactions, knowing how to have hard conversations, being an adult and treating others as such, and understanding the importance of giving feedback clearly and often. The job of leading humans is situationally dependent–each human has facets in the way of needs, drivers, personality, and skills innate and otherwise.

Playbooks tell us only so much on topics like this. Advice gets us only so far. At the end of the day, we come to know for ourselves as leaders what we know about our unique situation and what models and guidelines are useful–and what ones aren’t. This means often that there aren’t any easy right answers. Instead, we can aim for asking the right questions. 


Connect. Think. Lead. Adapted from the forward I wrote to a friend’s new book… Connect. Think. Do. I’d first gotten the call, an inquiry call for coaching, two weeks previous. In a follow-up…
Since Feeling is First My most favorite lines of poetry are from ee cummings: since feeling is first / who pays any attention / to the syntax of things / will never wholly kiss…
Being & Doing “What you are will show, ultimately. Start now, every day, becoming, in your actions, your regular actions, what you would like to become in the bigger scheme of things.” —…



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