How to Ask Your Team The Right Questions
Written by Dave Bailey
At University, I studied Mathematical Sciences. Each week, we were given tough maths problems to solve as quickly and elegantly as possible. When somebody didn’t know the answer, they were told the right answer. That’s just how school worked.
I carried this logic into business. If someone was struggling, I assumed that there was a right answer, and they just needed to be politely told it. I’d chime in with my answers, the intention being to help people solve the problem faster.
My proactive approach worked out at first . . . but when I started leading people, I quickly learned that real life isn’t like maths. In business, there are often many potential answers — and sometimes none of them are objectively ‘right’.
In the beginning, when I jumped in to tell the team what to do, they seemed to appreciate it. But over time, I noticed that volunteering my answers so freely was stopping my team thinking for themselves.
The Power of Asking Questions
Over the years, I began to learn the advantages of asking questions instead of giving answers. Not only do questions help people clarify issues for themselves before deciding how to move forward, they also strengthen their ability to ask themselves the right questions and to become independent of you.
However, not all questions are created equal.
To improve your ability to ask great questions, it helps to understand the different types of questions you can ask. Here are some contrasting categories of questions which are most likely to elicit deep contemplation.
1. Open versus Closed Questions
A closed question is one that you can answer with either ‘yes’ or ‘no’. They often start with the words, ‘Do you . . .’ or, ‘Are you . . .’ As the name suggests, closed questions tend to close down conversations, rather than open them up. In contrast, open questions empower the recipient to answer however they choose. For example:
- Are you okay? (closed)
- How are you feeling? (open)
2. Leading versus Curious Questions
When a prosecutor in a courtroom starts their cross-examination with, ‘Isn’t it true that . . .’, they are asking a leading question. Leading questions push someone towards giving the answer you want or expect. Curious questions, however, are phrased such that they could elicit any possible response, again provoking more thought in the answerer.
- Don’t you think it would be better to [your suggestion]? (Leading)
- What are your options? (Curious)
A leading question isn’t always a bad thing. In fact, the right open leading questions that assume an idea and encourage people to elaborate on its significance can help people refocus their attention, away from unhelpful thought patterns towards more healthy ways of thinking:
- Why is it important to be a good delegator? (Leading)
- What other reasons can also explain this issue? (Leading)
3. Complex versus Simple Questions
Have you ever watched a TV interviewer ask their guest a question that’s so long the interviewee needs to ask, ’Sorry, what was the question again?’ Overly lengthy questions, or strings of questions that run together, are too complicated to make people think carefully. Often, the simplest questions are the most thought-provoking — and the most challenging to answer.
- When you said X, it reminded me of the importance of Y. Given that Z happens, and bearing in mind A, B and C, how do you see this affecting your priorities vis-a-vis today’s changing world? (Complex)
- What’s most important to you right now? (Simple)
4. Informational versus Reflective Questions
A question whose primary purpose is to retrieve information is unlikely to foster deep thought. However, understanding the ins and outs of someone’s situation is not essential for asking a thought-provoking question. While reflective questions might have little informational payoff for the person asking, they can be very powerful for the person receiving.
- How did you do in this situation? (Informational)
- What was your biggest learning from this situation? (Reflective)
5. ‘Why’ versus ‘What’ and ‘How’ Questions
This is the most controversial insight I learned about asking questions. You’d think questions that start with ‘why’ would be the most powerful of all, but it turns out that often, they aren’t.
‘Why’ questions can trigger a defensive response from the recipient, even when they are asked with curious intentions. There’s also a slight nudge towards a single answer — usually starting with the word ‘because’ — rather than identifying many possible reasons.
Behind every ‘why’ question is a more powerful ‘what’ or ‘how’ question. For example:
- Why did you do that? (‘Why’ question)
- What outcomes did you expect when you did that? (‘What’ question)
Effective coaching is about asking the right questions at the right time. In his book, The Coaching Habit, Michael Bungay Stanier introduces seven powerful questions that every leader can use with their team:
- The Kick Start Question: What’s on your mind?
- The A.W.E. Question: And what else?
- The Focus Question: What’s the real challenge here for you?
- The Foundation Question: What do you want?
- The Lazy Question: How can I help? or What do you want from me?
- The Strategic Question: If you say yes to this, what must you say no to?
- The Learning Question: What was most useful or most valuable here for you?
Notice how all the questions combine the concepts outlined above: they are open, curious, simple, reflective, and start with ‘how’ and ‘what’.
One of my favourite questions to ask is:
“What do you mean when you say ‘X’?”
Asking for a definition of a word is so simple that it might be considered naive — which is why I love it so much. How many times have you been in a fierce debate over an issue, and it turns out you were both saying the same thing, but using different words. Meaning is meaningful.
Holding Space for Deep Thought
There is an obvious, but important, point about asking questions: when you ask a powerful question, you need to shut up. There are many factors that make this hard.
In particular, silence can be uncomfortable and there is a tendency to want to fill it. A powerful question often gets you thinking about it too. It’s easy to find yourself not paying attention to the other person, and instead focusing on the thoughts in your head.
To be a great asker of questions, you need to practice self-restraint — no matter how obvious the ‘right’ answer is to you.
Go Forth and Ask
As a leader, it pays to maintain a curious mindset. If you want to get people to think for themselves, you have to ask more powerful questions that help others shine a light into the dark areas of their mind that they have yet to organise.
We all need good questioning from time to time, to draw out insights and come to a conclusion. Who do you rely on to ask you questions? What do you think they might ask you?
Maybe, it’s time to find out.
Originally published Sep 24, 2019, last updated Jun 1, 2021
About Dave Bailey
Hi, I’m Dave Bailey and I coach tech CEOs from Series A to pre-IPO. Join 20,000 entrepreneurs who receive my new essay every week.
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