The question behind the question
What you think you're asking and what your team actually hears aren't always the same thing
“How’s it going?”
Spoken with a warm smile, genuine curiosity, and nowhere else to be, it’s an invitation. The start of a real conversation. Spoken with a shorter tone and a more piercing gaze? Suddenly it’s an audit, dressed up as small talk.
Same words. Completely different intent. And your team knows which one it is before you’ve asked your second question.
This week, we’re looking at one of the most common – and most consequential – micro-interactions in any leader’s day: the question. Specifically, what kind of questions you’re actually asking, and what your team is actually hearing when you ask them. Let’s explore.
It’s not what you’re asking – it’s what you’re really saying
There are two distinctions worth making here.
The first is the difference between questions that open and questions that close. Open questions create space – they invite thinking, signal trust, and leave room for the other person to go somewhere you haven’t anticipated. Closed questions narrow things down: they confirm, deny, or check boxes. Neither type is inherently wrong: sometimes you simply need to know whether something is done. But if the majority of your questions are closing things down rather than opening things up, you’re probably getting less from your conversations than you think.
The second distinction is more subtle, and arguably more important. It’s the gap between a genuine question and one with something else embedded within. An instruction disguised as an enquiry. An opinion dressed up as curiosity. A correction with a question mark tacked on the end to make it sound palatable.
You know the type:
“Have you thought about doing it this way?”
“Why did you approach it like that?”
“Wouldn’t it make more sense to...?”
Technically, yes, those are questions. Structurally, they are not. They’re your opinion – your concern, your preference, your correction – wrapped in a question mark on the theory that it sounds more collaborative.
The problem is it doesn’t work. People see straight through it. What they actually hear is “I don’t think you’ve got this right”, and they start to respond accordingly.
You are never just asking
This is the part that many leaders fail to realise.
When you are the most senior person in a conversation, you are never just asking a question. Even when you genuinely think you are.
I once worked with a CEO who shared that at the end of an all-hands meeting, she asked what she considered an innocent question about a minor operational matter. Something like: “I’m curious whether we’ve ever explored X?” She wasn’t directing anyone, she was genuinely curious. The meeting moved on.
Two weeks later, she discovered that a team had quietly diverted significant time and resource into something close to a full project around that very question. Because several people in the room had drawn a simple conclusion: if the CEO is asking, it must be important.
This is positional power in action. Your questions carry weight that you may not feel, and often cannot see. What reads as passing curiosity to you can land as clear direction to the people sitting across the table. The gap between intention and impact is always present in leadership – and it is amplified enormously by the power dynamic. This doesn’t mean stop asking questions; it means be clear and intentional about the impact of asking them.
You’re always training people how to treat you
I’ve worked with leaders who describe themselves as hands-on, curious, close to the detail. Leaders who were genuinely surprised – sometimes hurt – when their teams described feeling micromanaged or second-guessed.
“But I just ask questions,” they’d say.
They did. That was precisely the problem.
Many of their questions were a correction or a concern in disguise. So the team had learned, quietly and without anyone ever saying so, to hear them as such.
Over time, the impact is felt. People stop deciding independently. They check before they act. They spend energy managing upwards rather than thinking clearly. This isn’t a character flaw in the team – it’s a rational adaptation to an environment where their judgement is consistently, if subtly, questioned.
And here’s the irony. The leader who asks these questions in the name of staying across the detail ends up with less accurate information, not more. Because once people learn what kind of answer you want to hear, that’s what you get. Not the full picture, just the version of it that feels safe.
From interrogation to ignition
Questions used well can ignite thinking.
When a leader asks from genuine curiosity, something shifts. Questions that invite thinking rather than confirm compliance start to build capability, ownership, and the enhanced creativity and ideas that turn a good team into a great one.
People who feel trusted bring more of themselves to their work. And crucially, they develop the judgement to make good decisions without you. For a C-suite leader, that is the real prize. Not a team that executes your instructions well, but a team that can think – and act – for themselves.
For leaders this means leaning towards discussion and coaching before instruction, trust over control, asking and understanding rather than assuming. These are not soft ideals, they are priorities. And the questions you ask every day are one of the clearest signals of where your priorities actually lie.
Asking better questions
Asking better questions is a skill, and a genuinely important one. Like any skill, it takes practice – and the first step is usually noticing what you’re currently doing, which can be uncomfortable.
Here are a few places you might start:
Pause before you ask. What are you actually trying to find out? Is this genuine curiosity, or are you checking up, seeking reassurance, or steering towards an answer you’ve already formed? If it’s the latter, ask yourself whether a question is even the right vehicle, or whether it might be clearer and kinder to just say what you think.
Name your intention. Think transparency over efficiency. One additional sentence can remove a lot of ambiguity: “I’m asking because I’m curious about your thinking, not because I think you’re doing it wrong.” It feels like a small thing, yet it lands as a significant one.
Shift the framing:
“What’s the status?” → “What help do you need?”
“Why did you do it that way?” → “Walk me through your thinking”
“Have you thought about X?” → “What options did you consider?”
“What’s the plan?” → “Where are you feeling confident, and where are you less sure?”
Notice what you do with the answer. If someone responds and your instinct is immediately to redirect, correct, or jump in with a solution – you were probably asking to control, not to coach. Try asking a follow-up question instead of offering a view. See what happens.
Try the one-day audit. For one day, track every question you ask: who you asked, what you asked, and what you did with the answer. Fair warning: it can be a bit of a reckoning. You’ll realise quite how many questions you ask in a single day. Which is also, of course, the point. If you’re asking that many, it really is worth thinking about what they’re doing.
The question behind the question
Your team is already reading your intent. They’re doing it right now, in every conversation, in real time. The question isn’t whether they can tell the difference between curiosity and interrogation.
(Spoiler alert: they can.)
The question is whether you’re willing to look honestly at which one you’re actually delivering.
This week, think of someone on your team who has become a little less forthcoming over time – less likely to offer an opinion, push back, or flag a problem early. Notice what questions you have been asking them. What might they have been hearing?
This isn’t about becoming a soft leader, or relinquishing oversight or accountability. It’s about choosing a more effective route to the outcomes you need – one that builds your team’s capability rather than quietly eroding it.
Hit reply or leave a comment to share one question you’re asking differently this week – and what difference you noticed.
Restack
I enjoy a post with a good analogy… “Never wrestle with a pig. You both get dirty, and the pig likes it.” This is a nice exploration of using questions to build clarity aroun problems'.
Meme of the week
After some sunshine this week (for those not in the UK, this has been a rarity in 2026!) this one made me laugh ☀️
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