Questions You Should Ask Your Boss

Ask Don’t Tell: 3 Questions That Will Make You a Better Leader

You know that asking the right questions will make you a stronger leader. But it’s hard. Not all questions have the same impact. And it’s risky. You never know what the response will be–which means you need to stay fully present to be helpful.

“When you ask a question you’re giving up some of your power. It means you’re willing to sit in that discomfort for the good of another person’s growth.” -Michael Bungay Stanier

In my continued quest to surround myself and learn from others aligned with the Winning Well philosophy, I had an opportunity to interview Michale Bungay Stanier, author of The Coaching Habit: Say Less, Ask More, & Change the Way You Lead Forever.

3 Questions That Will Make You A Better Leader

1. “What’s On Your Mind?”

Have you ever noticed that’s the prompt that Facebook asks as the invitation to post? It’s so simple. Asking “What’s on your mind?” And then staying quiet and really listening to the answer can be a tremendous gift. Michael shares: “Because it’s open, it invites people to get to the heart of the matter and share what’s really important to them. You’re not telling or guiding them. You’re showing them the trust and granting them the autonomy to make the choice for themselves.”

2. AWE – “And What Else?”

Michael shared that in many circumstances the easy-follow-up, “And what else?” can open the door to deeper conversation. “There are three reasons it has the impact it does: more options can lead to better decisions; you rein yourself in; and you buy yourself time. ” It helps you to stay curious and not jump right into offering advice. The deeper understanding you have of the situation, the more you can discuss viable options.

Let’s play this out.

“What’s on your mind?”
“My boss is such a jerk, he keeps freaking out.”
“Oh, that sounds just terrible. That must be really hard.”
“And what else is going on?”
“Well, he’s extra mad this week because I screwed up the spreadsheet.”
“Oh boy, what happened there? (a slightly different version of ‘and what else’).”
“I don’t really know how to do pivot tables.”
“And what else?”
“And I’m not really comfortable with all the formulas.”

And BINGO… you’re down to a solvable problem

3. The Foundation Question– What do you want?

the coaching habitI must say this is my favorite question in his book. Michael shares:

“I sometimes call it the Goldfish Question because it often elicits that response: slightly bugged eyes, and a mouth opening and closing with no sound coming out. Here’s why the question is so difficult to answer. We often don’t know what we actually want. Even if there’s a first fast answer, the question, ‘But what do you really want?’ will often stop people in their tracks.”

Being able to know what we want, articulate it respectfully, and then be willing to accept an answer– know that sometimes it will be “no–is a vital component for having healthy conversation and productive relationships. As a leader, being able to help others identify what they want is a good place to start.

You can learn more about The Coaching Habit and download some additional free tools at

Posted in Communication and tagged , .

Karin Hurt

Karin Hurt helps human-centered leaders resolve workplace ambiguity and chaos, so that they can drive innovation, productivity and revenue without burning out employees. She’s the founder and CEO of Let’s Grow Leaders, an international leadership development and training firm known for practical tools and leadership development programs that stick. She’s the award-winning author of four books including Courageous Cultures: How to Build Teams of Micro-Innovators, Problem Solvers, and Customer Advocates and Winning Well: A Manager's Guide to Getting Results-Without Losing Your Soul and a hosts the popular Asking For a Friend Vlog on LinkedIn. A former Verizon Wireless executive, Karin was named to Inc. Magazine’s list of great leadership speakers. Karin and her husband and business partner, David Dye, are committed to their philanthropic initiative, Winning Wells - building clean water wells for the people of Cambodia.


  1. Active listening is one of several critical leadership success factors. It is about being able to be fully present. It is about removing filters as well as judgements, and to be focused, engaged, and sensitive to the needs and feelings of others.

    As per the Dalai Lama – “When you talk, you are only repeating what you already know; but when you listen, you may learn something new.”

  2. With the second question, I am reminded of the 5 Why’s, a methodology that is used in Lean process development/improvement. When analyzing a process, ask Why, then Why again and again five times until you uncover the root cause. Sometimes you uncover a different motivation than what you originally intended. Or sometimes it leads to a Lean solution. Great tips again, Karin!

    • The Five Why’s are very powerful … and I actually recommend NOT asking “why” in most conversations, mostly because it’s very hard to get the tone *just right* without it sound accusatory.

  3. I agree that “What do you really want?” is a great way to unlock what is going on inside a person! I was in an exercise once where we sat in pairs and asked each other what the other person really wanted. After we had answered, we went to round two: “What do you really want?” etc. It took several rounds to get to the real heart of what we each wanted. A very powerful exercise….

    • LaRae, that sounds so powerful. I think it works in our personal lives as well. I’ve been thinking about that in several contexts… some of the most important conversations we have come with ourselves 😉

    • It’s fascinating to me how quickly we drop down and get closer to what we really want … and how rarely it’s the first thing we say, when asked.

    • I must say, this was one of the most thought provoking parts of your book to me…. it seems so basic… but I do think for some reason many of us do hold back.

  4. Excellent & very right and practical questions, Karin.
    Very powerful questions indeed.
    There are 7 faithful servants (Questions) of modern leaders. There names are:
    What, How, Where, Why, When, Who and “Show me”.
    The last buddy is very effective and energetic.
    Zafarmanzoor. Engr. FFC. Pakistan.

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