The Three Questions Every Manager Should Ask Their Employees

Sara Jeruss
5 min readFeb 18, 2019

Back in 2016 I did Seth Godin’s altMBA, and one pre-reading assignment was The Coaching Habit by Michael Bungay Stanier. It’s a quick read. I was very skeptical at first. It seemed like the latest management gimmick. Use these 7 questions (for this post I’m going to focus on 3), and you’ll be a better manager. For reals? Especially when I read the first question:

“What’s on your Mind?”

I paid money to take a course that taught me to ask, “What’s on your mind?”? How could this possibly work? When I read it the phrase felt awkward and stilted. I don’t usually talk like this, so I thought people would catch on right away. But I decided to be a good sport and try it. On my wife.

We went for a walk and instead of the usual “How’s it going?”, I asked what was on her mind. And the shocking thing was, it worked.

Photo by Jamie Haughton on Unsplash

Just asking in a slightly different way was enough to completely change our conversation. Instead of small talk about the day, we spoke about her hopes and fears for the future. It was the best conversation we’d had in a long time.

So — why did it work? First, it sets the tone for the conversation. It’s just different enough that it’s an invitation for real talk. It sets an expectation that you’ll talk about what the person wants to talk about. Second, it takes you out of your “regular” mindset and signals to the other person that you want to listen.

Of course, you do have to listen for this to work, which brings me to the next question:

“And what else?”

This does three things. First, it shows that you know the person may have more than one idea they are chewing on or more than one issue they wanted to talk about. They don’t have to worry that they only get one chance to discuss something with you. You’re acknowledging that there is probably more than one thing on their mind.

Second,if you’re talking about a problem the person is facing, it let’s you help them brainstorm. If you’re reading this, you’re probably a good manager, and your team is probably smart, so the person has probably thought of more than one possible solution to the problem they are facing. Asking this helps and get past the surface answer — the “safe” answer that they probably think you want to hear because you are their manager.

And third, again, it forces you to listen. To step back instead of blurting out the answer that you probably developed in the 30 seconds it took you to listen to the question. And again, since you’re managing a smart person, they’ve probably spent more than 30 seconds thinking about this, so there’s a good chance one of 3 things will happen: 1) they’ve come up with some other solutions you haven’t considered yet — often these are better than your 30 second answer 2) The person brings up your answer, and some factors you hadn’t thought about yet that show why it’s not the best approach or 3) The person brings up the same approach you’d just thought of. But now it’s the person’s idea and they can be proud of executing on it, instead of just doing what their manager told them to do.

Of course, just asking “what’s on your mind?” and “and what else?” don’t always get to solutions. So the third question is:

“What do you think we should do here?”

I’ve modified this one slightly from the book, which suggests “What’s the real challenge here for you” and “What do you want?” Those are good questions too, and I could (and maybe will) do another post on them. But I like asking it this way because it acknowledges that, since this is a smart person, they may have some ideas about the issue they are facing. It shows that you respect them enough to want to hear their ideas. And it challenges them by setting an expectation that if they are coming to you with a problem, you will ask them how they think they should solve it. This lets the person practice being you — thinking about what they’d do if you weren’t there, gaining confidence that they can solve these problems, while still having you to offer coaching if there’s another approach they haven’t considered. Importantly, you only offer that coaching after you have truly listened to the person.

The Three Questions in Action — As a Managee

One of the best managers I ever had was Scott. Scott didn’t come into our meetings with an agenda. Instead, he created a safe space where I knew we could cut through the bs and talk about whatever issue I was facing that week. He asked some version of “what’s on your mind?” There were usually several things that I was debating bringing up with him, with an internal voice saying something along the lines of: Will I sound like a complainer? Do I need to talk about this small thing with my boss? He probably has much bigger concerns, should I bother him? Will he judge me for bringing this up? But the way he asked signalled it was safe.

And then he listened, and he didn’t jump in right away with an answer. He asked me questions along the lines of “And what else?” and “What do you think we should do here?”. These questions got me past those initial worries because he showed he was clearly interested in what I was saying. And becuse he always asked me what I wanted, I learned to bring him solutions instead of just problems. I didn’t always get what I wanted. But I felt empowered because he listened. He valued my opinion. That was enough to make me remember our talks and write about him now, 5 or 6 years later.

The Three Questions in Action — As a Manager

Since becoming a manager, I’ve tried to do this with my own teams. My reports consistently amaze me with their intelligence and creativity. When I’ve asked “What do you think we should do here?”, I’ve seen people suggest beautiful, efficient solutions. For example, one person had an idea about our lead generation strategy that probably saved hundreds of hours. The CEO loved it. We implemented it. We only took this approach because instead of telling my report to do it my half-baked way, I asked her what she thought we should do. And one comment really stuck with me — when after I said “What do you think we should do?” she said “No one’s ever asked me that before.”

I’m not perfect at this. I can think of many recent 1:1s where I’ve talked way too much. It takes practice and, like any new technique, you’ll make mistakes. But I promise that if you stick with it, if you consistently ask your team “What’s on your mind?”, “And what else?” and “What do you think we should do here?”, you will be a better manager. Your team will perform better. It’s easy. Go get started.

If you end up trying any of these questions, I’d love to hear from you (you can comment or email me at tltcoaches@gmail.com). And if you’re interested in coaching, you can find me at The Leadership Team.

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