The power of the question: how to coach in the moment

This week I continue the series on coaching your team when you are a leader or manager.

In previous weeks, we’ve covered why this is important and when you should do it. So, if you haven’t read those posts (welcome new subscribers!) it definitely will be worth your while doing so.

This week we're going to look more closely at how to coach. And it is worth re-emphasising, that what we’re considering in this series doesn't mean that you have to conduct formal coaching sessions with structured models and processes that require weeks of training and practice.

This is about coaching in the moment, when you turn some of the interactions you have with your team members into growth opportunities.

What coaching really means

Coaching is fundamentally about helping someone think differently so they can solve their own problems. When you are coaching, your job isn't to provide answers. It's to help the other person discover answers of their own.

And that requires you to ask questions. Because if you simply tell people what to do, they don’t engage with the issue at a deeper level. They simple execute your solution rather than thinking more deeply about it and thereby developing the capacity to devise solutions for themselves.

The types of questions that don’t work

You might think asking questions is straightforward. After all, we do it every day. But there's a world of difference between a question that sparks genuine reflection and one that leads nowhere, or worse, one that sounds patronising or aggressive.

So, we’ll start by looking at some of the ways in which we can get our questioning wrong.

Closed questions shut conversations down: If the answer can be a simple 'yes' or 'no', you've probably asked the wrong question. Consider the difference:

  • "Did the meeting go well?" This invites a one-word response and signals you're not particularly interested in the detail.

  • "What happened in the meeting?" This opens up the conversation and shows you genuinely want to understand.

Suggestions dressed up as questions: This is perhaps the most common trap. We've all done it. You ask something like "Have you considered speaking to the finance team?" or "Wouldn't it make sense to revise the timeline?" These sound like questions, but they're really instructions with a question mark attached. The person on the receiving end has two choices: agree with you or push back. Neither leads to genuine thinking.

Stacking multiple questions together: Do this and it just creates confusion. If you are just thinking out loud without being clear in your own mind what you want to ask, you can end up with something like this: "So what's the status on that project, and are we still on track for the deadline, and have you looped in the stakeholders?" The other person doesn't know which question to answer first — and often answers none of them properly.

Questions beginning with 'why': These can sound passive-aggressive and tend to put people on the defensive. You will , do doubt, have experienced this yourself. "Why did you do it that way?" can feel like an accusation. ‘Why’ questions are also very often unproductive. They will often lead to over-analysis of the problem, without moving the conversation towards a solution. The worst why questions, in my view, are when someone asks why somebody else did something. How the hell do I know? The best I can do is speculate.

A more productive approach is to say something like "Take me through your thinking on that", "What led you to that conclusion?", or “What got us to this point?”.

Questions that unlock thinking

Questions that are effective open up the other person's mind and take them somewhere new. Here are some ways you can frame your questions to achieve that result.

Keep your questions brief. Aim for somewhere between seven and twelve words. Shorter questions have more impact. They cut through waffle and force clarity. Long, meandering questions are only ever going to produce vague repsonses.

Lead with 'what'. I'd encourage you to make it a habit to begin your coaching questions with the word 'what'. It's remarkably effective:

  • "Have you thought about how to fix this?" — This is a closed question. It can be answered with a simple yes or no, and it subtly implies that you have a solution in mind or that your team member should have thought of it already.

  • "What options are you considering?" — This is open. It invites genuine exploration and keeps the ownership with the other person.

Some of the most effective coaching questions are very simple. "What do you want to happen?" or "What matters most here?" These questions cut straight to what's important.

Use 'how' when it's time to act. Once the person has worked through their thinking and identified a way forward, 'how' questions help them plan. Examples are questions like: "How will you approach that?" , “How will you carve out the time?”, or "How do you think they'll respond?". The last one is a bit speculative, but it is forward-focused and solution oriented as it looks to uncover any blockers that might arise.

Don't be afraid of feelings

One thing that can catch new leader-coaches off guard is emotion. When you ask good questions, you sometimes tap into frustration, disappointment, or even tears. This can feel uncomfortable.

But emotion is central to how we make decisions and process experiences. If someone becomes upset during a coaching conversation, don't rush past it. Don't offer empty reassurances. Sit with it. A question like "How are you feeling about this right now?" or "What support would help?" shows that you're taking the whole person seriously, not just the task at hand.

The message here is simple: ask more, tell less. And when you do ask, make sure your questions serve the other person's thinking — not your own agenda.

That's how growth and development really happen.

Reference

Manager as Coach - the New Way to Get Results, Jenny Rogers (2012), Professional Press.

How I can help you

Coaching - I have a few spots available for 1 to 1 coaching. I can help you with any of the people leadership challenges you might be facing. There are more details here.