The Coaching Habit: Say Less, Ask More, & Change the Way You Lead Forever

Monthly Book Review

A few years ago I attended an event where Michelle Obama was interviewed on the main stage by Ashley Smith, the wife of Qualtrics founder Ryan Smith. It quickly became apparent that Ashley was more interested in focusing on herself than the interview with Michelle Obama, which made watching it extremely uncomfortable for everyone (I kept looking around at the faces of those watching, everyone’s expression mirroring my own 😬).

Fortunately, Michelle Obama handled it very well and kept redirecting the conversation like a skilled interviewer. Which is who should have been on stage.

Part of the problem was that the questions meandered, lacked focus, and kept veering off topic. Sound familiar? Many of us have these problems in our regular meetings as well. Especially in one-on-one meetings with our teams. It’s easy to talk for a while about sports, the weather, life, etc. And while these are good topics and can help bridge gaps and build relationships, if we spend all our time talking about them, we’ll never get to the important parts of meeting with individuals on our teams.

We all need to be able to ask good questions. And that’s why I wanted to read The Coaching Habit by Michael Bungay Stanier.

Overview

This book is a relatively quick read and focuses on building better coaching habits by asking better questions. The core premise is simple: coaching isn’t an occasional, formal event—it’s something done in 5- to 10-minute conversations every day or as we get the opportunity.

The author argues that most of us (especially leaders) fall into the “advice trap,” where we jump in too quickly with solutions and try to fix everything. While jumping in may feel helpful, it creates dependency, burns us out, and stifles growth in the people we lead. The antidote to this is a set of seven simple questions that help us as leaders slow down, stay curious longer, and coach more often.

As a product management leader, one of my primary goals is to constantly ask more (and better) questions. I also want my team to be asking better questions as well. So what are the questions this book suggests and how can we apply it to our work and other areas of our lives?

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Key Takeaways

I won’t get into all seven questions, but let’s review a few of the best.