Box of Crayons Blog


Top Questions Every Manager Should Know

One of the questions I hear all the time is, “So what are the best coaching questions for me as a manager and a leader?” Tune into this podcast as I make the case for giving a little less advice and having a little more curiosity. I share:

  • The three different types of questions and when they’re most powerful
  • The importance of tone
  • Why being lazy could be your best move
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Full Transcript

So, look, I get asked all the time, “So what are the best coaching questions for me as a manager and a leader?” And I’ve got some pretty strong opinions on that. But before I go and share with you what I think are some of the key coaching questions, let me pull you back to why you would even care about that. And one of the most influential articles I’ve read is by a guy called Daniel Goleman. You may know him. He’s most famously connected to the whole idea of emotional intelligence. He didn’t come up with that idea but he certainly popularized that idea. And he’s still an influential writer and thinker.

But way back when, in the year 2000, he wrote an article for the Harvard Business Review. It’s called “Leadership That Gets Results.” And this is based on research, and he came to find that there were six different leadership styles that tended to show up in organizations. And what was interesting is that each one of those leadership styles was useful, important and had an impact. The styles were things like visionary or democratic or pace-setting or commanding. And one of them was coaching.

Now, not only did they define the different leadership styles but they looked at the impact these different leadership styles had, and one of the interesting things I found about coaching, because, you know, at Box of Crayons we’re all about the coaching, they found that coaching was the least utilized of all leadership styles, even though it would have the most impact on employee engagement, an impact on culture and actually has a pretty significant impact on the bottom line as well.

Now, that was 15 years ago. Has anything changed? I’m going to say probably not a whole lot. Coaching is still a massively underutilized approach to leadership and management.

Now, part of what Goleman found is that good leadership, great leaders, know how to use all six leadership styles at the appropriate time. More typical leadership, more average leaders, use two, maybe three, different approaches. So here’s my wish for you, because my guess is you’re probably a manager or a leader and if you’re not now, maybe you’ll become that, I would love you to have more of the coaching mix in the way that you work. In other words, and this is kind of the fundamental behaviour shift that we stand for at Box of Crayons, I’d like you to give a little less advice, you know, be a little less the expert, and have a little more curiosity. Ask some more questions.

So that sets up nicely, doesn’t it, for you to ask me, say, “Michael, okay, if that’s the case, what are the questions I should be asking?” Well, there’s actually lots and lots of great questions out there and in fact, one of the things I’m going to direct you to right now is actually a series, a video series, we’ve been doing at Box of Crayons separate to this one called My One Best Question. And rather than me just going, “Oh, what do I think are the best questions?”, I’ve asked thought leaders and executive coaches and managers and leaders, probably just like you, what are their one best question.

So one of the things that you can do is go to the Box of Crayons website,, B-I-Z, or B-I-Z [pronounced like zee], and actually look for the one best question series under the Resources tab. And there’s going to be at least—I’m going to say at least 80 questions there that you can tap into and make the most of. So go there first of all and see which questions other people like so you can pull the ones you like the best.

The second thing I want to do is just talk about three different types of questions, the what, the how and the why, and when they’re most powerful.

Now, you’ve probably heard of the power of why. I mean, Simon Sinek is today the flag waver for the power of why. You know, his books start with “Why.” Huge bestseller. He’s got a fantastic Ted Talk on this, and truthfully, there’s something very powerful about asking why.

Peter Senge championed the why before Simon Sinek came along. He —Senge— made this five-why process popular. That’s when you ask the question why five times to get to a root cause.

But I’m going to say you know what, ignore those two for now for the day-to-day coaching questions because when you ask a why question, there’s a couple of things at risk. The first is you have to get the tone spot on or, if you don’t, the why can sound very judgmental, very critical. Instead of being genuinely curious, going, “Why did you do that?” sounds like, “Well, why did you do THAT?” And actually that doesn’t help the conversation at all.

The other thing that’s less strong about a why question typically is it typically generates a story, sort of history, some sort of justification or background. And why you’re typically trying to find that out is so that you can get more data to provide advice to the person who’s asking—who you’re engaged in conversation with. And I’m going to encourage you to become a lazy coach, a lazy manager, and a why question doesn’t typically help you do less work so that they can figure out the answers themselves. So that’s the why question. So I’m asking you to try and put those aside.

“How” questions can be very useful indeed but notice that as soon as you start asking a how question it’s all about the, “How are you going to make this happen? How are you going to get this done? How are you going to implement this?”

And obviously there’s a place for that but I think in most organizational life the how question shows up way too soon. And what most people are trying to do is they’re trying to create the action plan when they don’t even know what the right problem is, let alone what the best solution to that problem might be. There’s such a rush because action is at a premium in our organizations that they’re immediately into the how before they’ve really figured out the what.

And that’s why I’m such a big champion for questions that start with “what”. This could be the habit you take away from this podcast, is practice starting all of your questions with the word “what” because that’s what actually allows people to think, to reflect, to drill down, get new insights about the situation, insights about themselves, insights as to what the new solution might be to drive forward potentially great work.

So that’s the second point I wanted you to make: Just the difference between the why, the how and the what. The third point, I’m actually going to share with you what I think is the best coaching question in the world, and this is going to be easy for you to remember because the initials are AWE. That stands for awesome, A-W-E. And the question is this: And what else? Look, I know that doesn’t sound like a big question or an important question but here’s why I think it’s such a fundamental question for you.

The first thing somebody says to you when you ask a question is never the only thing and it’s rarely the best thing. So it’s a way of generating new insights and additional insights from the first question that you asked.

The second thing, and this is perhaps more important, is it’s a self-management talk to stop you being triggered by their first answer and leaping in to try and fix things and do things differently. What I want you to do is stay lazy, and one of the most powerful ways of staying lazy as a coach and as a manager is to ask the question, “And what else?” Not because you’re not committed to them. Not because you don’t want to help them, because you do; it’s rather because you’re going to help them do the work which helps them get more buy-in to the solution. It helps increase their own capacity. It helps increase their own wisdom, and in doing so you’re driving increased self-sufficiency which helps them and helps you as well.

So if you’re sitting there, you’re a manager, you’re a leader or you just interact with human beings, those are some of my top tips about asking coaching questions. Tap into the My One Best Question series.

You can see an increasing reservoir of questions there on our website, Secondly, know the difference between the what, the how and the why and choose the appropriate type of question at the appropriate sort of time.

Hint: Ask “what” questions far more than any of the other ones. And finally, if you have one question to take away from this, it’s the question “And what else?”


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