Top Leaders Share the Best Question They've Ever Been Asked
The episode is leadership content rather than market or practice commentary, but its focus on self-awareness, challenging assumptions and spotting blind spots is framed around how senior people make decisions. Principals and managers deciding where to spend listening time should know it is a compilation of prior interviews built around a single theme, not a discussion of advisory firms or portfoli
Summary
By the family offices deskEric Becker of Cresset assembles past conversations with executives into an episode about the questions that shape leadership. The through-line is a question Becker says came out of a contest he ran with 80 board members and 20 CEOs — "What am I tolerating that I shouldn't be?" — which he describes as both a personal practice and a lens for decision-making. Chapters feature guests including Mindy Grossman, Chris Cocks, Biltmore leaders, Cheryl McKissack Daniel and Rick Rieder, Kim Seymour and Scott Kirby, and Stanford's Bill Burnett and Dave Evans.
- Becker traces the episode to a contest in which he asked 80 board members and 20 CEOs for the best question they had asked or been asked.
- The winning response — "What am I tolerating that I shouldn't be?" — became a personal practice for Becker.
- The description frames the discussion around self-awareness, uncovering blind spots, purpose-driven leadership and clearer decisions.
- Chapters cover individual guests on walking away from something, getting to the truth, purpose, better decisions and life questions.
Chapters
From the publisher’s description| Time | Chapter | Length |
|---|---|---|
| The Questions Great Leaders Ask Themselves | 2 min | |
| Mindy Grossman: What Would You Walk Away From? | 3 min | |
| Chris Cocks: How Great Leaders Get to the Truth | 2 min | |
| Biltmore Leaders: What’s Your Purpose? | 2 min | |
| Cheryl McKissack Daniel & Rick Rieder: Better Decisions | 2 min | |
| Kim Seymour & Scott Kirby: Questions Great CEOs Ask | 3 min | |
| Stanford’s Bill Burnett & Dave Evans: Better Life Questions | 4 min |
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