Do you actually know how to ask the right question?
A winter footmuff recommendation led me to think about the questions leaders ask, the context they contribute and why feedback is not proof of failure.
Leading People · Coaching · Feedback · Decision-making · AI in Real Work
I was on voice mode with ChatGPT, trying to work out what would keep my daughter warm on winter walks. I was describing a winter footmuff, one of those padded bags that fits into a pushchair, made from something like puffer-jacket material. It was a fairly ordinary conversation about buying something useful. It also became the starting point for this article.
This article is inspired by real workplace and leadership experiences. I do not use real names, company names or identifying details. Roles, teams, organisational structures, projects and business context may be removed, generalised or combined to protect the people and organisations involved while preserving the underlying leadership reflection. Where conversations are referenced, wording may be edited for clarity and anonymity.
ChatGPT recommended an option, and I could have accepted it and moved on. Instead, I wanted to understand why that one, why it cost what it did, and why I should choose it over the alternative. I kept coming back to the context. I wanted something for proper outdoor walks, so the recommendation needed to make sense for that use.
There was no particularly clever technique involved. I was listening to the answer and asking about the parts that needed more explanation before I could make a decision. The questions came from what I was trying to achieve, rather than from a list I had prepared.
As the conversation went on, I started thinking about how we do this at work. Someone brings us a presentation, a proposed process or a recommendation, and we have a choice about how carefully we engage with it. We can accept it, or we can help examine the reasoning and bring something else into view. Even when we choose to ask questions, though, I think there is a difference in what those questions actually contribute.
The question needs some context
A crucial part of leadership, for me, is being able to think critically about what is in front of you. That includes challenging assumptions, noticing gaps and considering how a decision might affect something beyond the immediate discussion. It starts with stopping long enough to listen to what somebody is actually saying.
Questions about whether someone has aligned with another team or considered the risks can be useful. Sometimes those are exactly the gaps in the work. But if I could ask the same questions in almost any meeting, I need to consider whether I am responding to the proposal or simply working through my usual routine.
If someone is presenting a new process, I might know about a strategic discussion that could affect it. I can share what was discussed and then ask, ‘What impact do you think that has on the process you’re proposing?’ Now there is something specific for us to examine together. I have connected what they are presenting with something they may not yet have had the opportunity to consider.
That is the kind of question that makes me trust a leader's involvement. I can see that they have listened, understood enough to make a connection, and offered a perspective that could improve the work. Their contribution becomes visible through the reasoning behind the question.
It also gives the other person something they can challenge. They may understand the process better than I do, or explain why the connection I have made does not change their recommendation. I need to be open to that answer, because asking a thoughtful question does not make my interpretation the correct one.
When the questions never lead anywhere
I once had a leader who followed the questioning approach encouraged by coaching frameworks and leadership guidance. They would ask the questions and leave the team to work towards the answer. I understand the intention behind that, because giving people room to think for themselves matters.
Over time, though, the team became frustrated. They could answer the question, but they were still left wondering what the leader thought, what decision followed, or where the conversation was supposed to take them. The questioning continued without enough connection to the bigger picture. Eventually, that affected the leader's credibility with the team.
My difficulty with the approach was how little seemed to happen beyond the standard questions. The team needed the leader to engage with their answers, contribute relevant context and help move the work forward. Asking another question could not always provide what was missing from the previous exchange.
In a recent training session, we discussed how questions can help people think more broadly. I agree with that. A question can help somebody notice a possibility they had not considered or examine an assumption they were about to build on. The part I want to be careful about is turning that into my default response regardless of what the conversation needs.
Sometimes I need to clarify my understanding before I can contribute anything useful. Sometimes I need to share information, explain a constraint or make a decision. If someone has done the thinking and brought a recommendation, I should be able to engage with it beyond asking them to produce another answer. Otherwise, I may be calling something coaching while leaving them without the direction they came for.
I want my experience to help me recognise connections and offer a wider view. That only becomes useful to someone else when I share enough of the reasoning for them to understand it. Keeping the context in my head while asking them to discover the answer is a strange way of helping them develop.
The conversation with ChatGPT brought that responsibility back to me. A recommendation does not remove the need for me to consider the circumstances, draw on what I know and decide what makes sense. The same applies when the recommendation comes from a person. Whatever support I use to develop the thinking, I remain responsible for how I engage with it and what I decide to do.
Being on the receiving end
There is another side to this that I think matters just as much. One of my managers asked how they could anticipate the questions I would ask, because their work kept coming back with more comments and review notes. I understood why they wanted to know. It is frustrating to put effort into something and still feel there is another round of questions waiting.
My answer was that they could not anticipate everything. They could not know every conversation I had been part of, every experience I might be drawing on, or what new information had changed my perspective that day. Nor could they do that for every other leader who might review the work.
That does not give me permission to change the standard according to my mood. If my question comes from context they could not have known, I need to share it. I cannot treat information they were never given as something they should have anticipated. The question needs to help them understand what has changed and why it matters.
I also do not want that conversation to suggest there is no point preparing. I would still expect someone to examine their own assumptions, consider the questions they can reasonably foresee and understand the reasoning behind their recommendation. That gives us something substantial to work with. It also means they can explain their choices when another perspective enters the discussion.
What I would not want is for their entire preparation to become an attempt to predict me. There will be something I have heard, or something another person notices, that they have not considered. If the goal is to eliminate every possible question, even useful feedback can begin to feel like evidence that they have failed.
A question might reveal a gap that needs more work. It might also reveal that the explanation was unclear, that someone has different information, or that we disagree about a trade-off. Those possibilities deserve different responses. I would rather understand what the question is telling us than treat the existence of a question as a verdict on the person who prepared the work.
I need to apply the same openness to my own contribution. Someone can answer my question and still reasonably stand by their recommendation. They can also ask me to explain why I think a particular issue matters. My seniority should not turn every question into an instruction to change the answer.
There is a point where the discussion needs to lead somewhere. We may need to adjust the proposal, resolve an uncertainty or decide that the work is ready to move forward. Welcoming questions does not mean keeping someone in review indefinitely. I still have a responsibility to help make the next step clear.
What I want to encourage is thoughtful preparation with enough room left for other people to contribute. None of us brings every experience or perspective into the room. That is part of the value of discussing the work together, provided we are willing to listen when the answer changes our own thinking too.
I would rather leave a conversation understanding something I had missed than protect a recommendation from every challenge. For the person asking, that means making the question worth considering. For the person answering, it means allowing another perspective to become part of the work without assuming that its arrival diminishes what they have already done.
Don’t aim for no questions. Make room for different perspectives, and welcome the questions they bring.
