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Questions that actually lead to good answers

Here are seven key questions to help leaders have better conversations with employees and help both parties listen and act with more focus.

6 min read



Leading others, in whatever form it takes, is rarely about anything particularly exciting. It’s often about being clear about the task and expectations, about listening, and about feedback that acknowledges what must improve going forward.

That’s not everything, but that portion of it is not insurmountable for most leaders. Unfortunately, the natural tendency for many of us is to assume everyone has the same mental picture of the work and the goal, to delight in the sound of our own voice, and to be uncomfortable or really bad at giving feedback.

So what’s the good news about this good news/bad news scenario? Well, it’s most of us have good intentions. We want to be good leaders, good coaches, good listeners. But we’re struggling to do so.

Fortunately, there is a book out this year that might be able to help — both those you coach or manage and you. It’s “The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever” (Box of Crayons Press, February 2016) by Michael Bungay Stanier.

The premise is based on something many of us are familiar with: Work is too busy already. How can we get everything done while also maintaining some semblance of sanity? How can we ensure, then, that the work we’re doing has purpose and impact? Stanier starts here as a root reason why better coaching can help.

He tackles those human tendencies I mentioned up top: Assumptions, talking too much and trouble with feedback. Yes, he wants you to listen more. But not just listen. His seven key questions are designed to guide conversations fruitfully and allow for interjecting or clarifying questions when necessary. These questions are designed to bring out better answers.

There’s a lot to take away from the book. In fact, if you manage people, you’ll want to go through the book, take notes, and compare and contrast to your own question-making process. For today, I want to look at how the book addresses what I’d label the fundamental concerns of SmartBrief on Leadership:

  • How do we get better, slowly and deliberately, at being better leaders, communicators, thinkers and people?
  • How do we do this while also staying in business?

We must be deliberate

Change almost always requires new habits. And building a new habit for Stanier requires a concise goal, stating it out loud (“make a vow”), practicing it — a lot —  while knowing what triggers the old habit and how we can get back on track when (inevitably) we slip. Stanier starts his book here, not only to help us be prepared for his seven big questions but also, I think, to remind us that building better habits, being a better leader and manager, is hard work and not always fun.

Ask questions one at a time

This piece of advice works on two levels. First, literally ask one question at a time and wait for an answer. Second, the seven key questions in “The Coaching Habit” are in a deliberate order. You can start with the essential question No. 1, “What’s on your mind?” and get better at moving past small talk and toward the beginnings of a productive meeting. Then, you can master the next question and the next. Habits take time. You know this, but remind yourself once in a while.

Help others, help yourself

This book is not advocating some kind of charity, in which the leader changes his or her questioning style, helps others and gets relatively little in return. Instead, Stanier says, one of the biggest benefits of asking the right questions, listening to the answers, following up and acknowledging what you’ve heard is that you eventually work less. You’re no longer playing the hero, persecutor or victim, as Stanier describes the three dysfunction and co-dependent roles within the Karpman Drama Triangle.

To avoid those traps (well, at least most of the time) Stanier suggests an offensive: Either the question “How can I help?” or “What do you want from me?” Both place the ball in the other person’s hands, prevent you from swooping in with “answers” and still leave you the option of declining an outrageous or impractical request.

“What’s essential to realize is that regardless of the answer you receive, you have a range of responses available to you.” ~ Michael Bungay Stanier

Be strategic in what you (and they) commit to

There’s a wonderfully simple idea on page 165 of “The Coaching Habit” — it’s a single sentence that takes up the whole page.

“A ‘Yes’ is nothing without the ‘No’ that gives it boundaries and form.”

Much like Dan Ward in “The Simplicity Cycle,” Stanier understands the practical concept of limited time and brain capacity while also understanding the aesthetic of how decisions beget others, even the decision to do nothing.

Most advice sticks to one or the other — “say ‘Yes’ more!” or “learn to say ‘no” — and while each is responding to an exaggeration, those responses can neglect to acknowledge the need for balance and situational context. Stanier, anticipating this, presents a chart of good reasons to say “Yes,” along with bad reasons to say “Yes,” with corresponding areas for “No.”

He also realizes that we can’t always say “No” depending on the person making the request or the circumstances. In those cases, other responses may be appropriate, including ways to say “Yes,” but more slowly.

Ideally, this process leads to smarter decision-making, better focus and results delivered on things that matter, not simply whatever is placed in front of us.

Find what works for you

There’s much more than the little I’ve been able to cover here in “The Coaching Habit.” The good thing is that the book can serve as a living document — full of broad yet practical, organized yet not predetermined advice that can be read straight through or consulted as needed for years to come.

You’ll find “The Coaching Habit” a good place to start, especially if you don’t have a system for listening to your team, helping them help themselves (and you!) and focusing on the work that delivers the most impact.


James daSilva is the longtime editor of SmartBrief’s leadership newsletter and original content, as well as newsletters for entrepreneurs, HR executives and various other industries. Find him at @SBLeaders or email him.