The Coaching Habit

Sriharsha

February 6, 2025

leaders skills, personal development trainings, Leadership coaching

The Coaching Habit: Why Every Transformation Leader Needs to Ask More and Tell Less

I recently reread The Coaching Habit: Say Less, Ask More and Change the Way You Lead Forever
by Michael Bungay Stanier, and it landed differently this time. A few years ago I read it purely as a
coach. This time I read it as someone who spends most of his week helping organizations execute
large scale transformation, and the book felt just as relevant to that work as it does to coaching
itself.
Transformation programs fail less often because of the framework and more often because the
leaders driving them default to telling instead of asking. When a program hits friction, most leaders
reach for direction. Stanier’s argument is that the better instinct, and the harder one to build, is to
ask a good question first.

Why this matters more now than when I first read it

Coaching isn’t just for professional coaches—it’s an essential leadership skill. Whether you’re a manager, director, VP, or executive, you need to develop a coaching mindset to help your team grow. But let’s be honest—most leaders are busy. The idea of adding “coaching” to an already packed schedule can feel overwhelming.

That’s where this book stands out. Michael Bungay Stanier teaches you how to coach in less than 10 minutes, making it a seamless part of your daily conversations.

Coaching Is a Habit, Not a One-Time Event

Every leader I work with today is short on time and long on pressure. Transformation initiatives, AI adoption and constant reorganization have made “I don’t have ten minutes to coach someone” feel like a reasonable excuse. Stanier’s central promise is that you do not need an hour. You need one good question, asked well, in under two minutes. That is a realistic bar for a busy transformation leader, not an aspirational one.

Seven questions worth building into your week

The book’s real value is a short set of questions that force better conversations. A few that I now use constantly in my own coaching and transformation work:

• What’s on your mind. A better opening than “how’s it going,” because it skips the small talk and gets straight to what actually matters to the person in front of you.
• And what else. The first answer someone gives is rarely their only option. This question alone will surface two or three better ideas most of the time.
• What’s the real challenge here for you. The first problem someone raises is rarely the deepest one. This question buys you the extra thirty seconds it takes to get past the symptom and closer to the cause.
• What do you really want. People often ask for what feels achievable rather than what they actually need. This question separates the two.
• How can I help. This one stops you from jumping in to fix things before you have actually been asked to.

Silence and acknowledgment do more work than advice

Two habits from the book stuck with me beyond the seven questions. The first is silence. Give people time to think before you fill the space, even when it feels uncomfortable. The second is acknowledgment. A specific, genuine “that’s a sharp read on the situation” does more for someone’s confidence and ownership than most advice ever will.

Where this fits into transformation leadership

None of this replaces the hard mechanics of running a transformation: the roadmaps, the governance, the metrics. But the leaders who get the people side right are consistently the ones whose transformations outlast their own tenure. Asking better questions is one of the cheapest, fastest ways to get there. Stanier’s book is not a coaching manual you read once and shelve. It is a short, practical habit worth building into how you lead through change, starting this week.