The Art of the Better Question
Updated: Jul 2
Most leaders ask a lot of questions. Few have ever been taught how.
Questions are neutral. Except they’re not.
The words we choose, the order we use them in, the way we hold the silence after - all of it lands somewhere in the nervous system of the person being asked. It either opens them up or closes them down. Creates safety or activates threat. Generates thinking or shuts it off.
The gift of my work is that I get to witness this up close.
Recently, a client came into a session frustrated - and has kindly given his permission for me to share this, because he felt it was too useful to keep to ourselves.
His team, he said, never gave him straight answers. Meetings went in circles. He couldn’t get to the bottom of anything. We spent some time looking at the questions he was actually asking.
“Why didn’t this get done?” “Why did that call go the way it did?”
We swapped a few words. Not the intent - just the framing. What instead of why. Open instead of closed.
His next team meeting felt like a different room. Same people. Same stakes. Different questions.
Questions Create
They don’t just collect - they generate
Most leaders use questions as extraction tools. They want data. Confirmation. Evidence that their read on the situation was right.
This shows up differently depending on where you sit. For senior leaders in large organisations, it can look like using questions to confirm a read you’ve already formed. For founders, it often runs deeper - when you’ve built something from nothing, your pattern recognition is finely tuned and fast. Both are using questions as confirmation, not exploration. And both pay a price for it.
The most powerful questions don’t extract anything. They generate something that didn’t exist in the room before.
When we’re asked a genuinely open question - one with no embedded answer - something shifts neurologically. The brain moves from defensive scanning to exploratory mode. We stop justifying and start thinking. Michael Bungay Stanier captures this in The Coaching Habit: staying curious just a little longer, rather than rushing to advice or action, changes the register of a conversation entirely. People arrive somewhere they wouldn’t have reached alone.
That’s not soft. That’s strategy.
The “Why” Problem
One word that quietly activates threat
Here’s what most leadership development doesn’t tell you. The question leaders reach for most instinctively - why? - is frequently the least useful one in the room.
“Why did this happen?” “Why did you go that route?” It sounds like curiosity. It often isn’t.
In David Rock’s SCARF model, questions that imply evaluation - even subtly - activate the brain’s threat detection system. The same neural circuits that fire when we sense social danger fire when someone asks us to justify ourselves. People don’t think more clearly when threatened. They defend. They protect. They go narrow.
Swap “why” for “what” and the same question lands in a completely different part of the nervous system. “What factors led to this outcome?” is not softer. It’s sharper - because you’ll actually get an honest answer.
Tasha Eurich’s research on self-awareness, published in Insight, found that introspective “why” questions often fuel rumination rather than clarity. We spiral rather than examine. “What” questions move us forward. They’re solution-adjacent by design.
“Why isn’t the team performing?” is a question that puts you at the centre - judge, jury, frustrated observer. It works the same way whether you’re running a division or a startup. “What does the team need from me right now to move forward?” is a question that puts you in relationship with the problem. One closes. The other opens.
Back to my client. The shift from “why didn’t this happen” to “what got in the way” didn’t just change the words. Within two sessions, his team stopped being defensive and started being useful.
The information was always there. The question was getting in its way.
Trust Is Built Here
More than you might expect
One of the things I notice most consistently in work with senior leaders and founders is how rarely people feel genuinely heard. Not just listened to - heard. It’s a different experience, and most people can tell the difference immediately, even if they don’t name it.
The more senior you become - and this is especially acute for founders, where the stakes are existential and the pace is relentless - the more your team will manage what they say and how they say it around you. Good questions - genuinely open ones - are one of the few tools that can cut through that. They signal that you actually want to know.
What separates a good question from a great one isn’t complexity. It’s what it communicates underneath. That you’re genuinely curious. That the answer matters. That you haven’t already decided what you think.
Curiosity is one of the most trust-building behaviours available to a leader. Questions are simply how it shows up in practice.
Eurich’s research found that leaders who created the most psychological safety weren’t necessarily the most charismatic or the most experienced. They were the most genuinely interested in other people’s thinking. Real interest, not performed interest, is harder to fake than most leaders assume. People can feel the difference in the room.
Five Shifts Worth Making
Not a script - an orientation
Follow up before moving on. “Can you say more about that?” is one of the most underused questions in senior leadership. It signals that the answer actually landed - and that it was worth staying with. Most people have rarely had that experience in a work conversation.
Open over closed, every time. “How did the project progress?” gives you information. “Did it hit the deadline?” gives you a yes or no and closes the door. One invites a person in. The other puts them through a filter.
Sequence deliberately. The order of questions is as important as the questions themselves. Start wider, build safety, move to specificity. A team that feels evaluated from the first question will answer accordingly. A team that feels explored will tell you what you actually need to know.
Read group dynamics, not just individuals. “How do you think the team will respond to this?” shifts a one-to-one exchange into something collective. It creates permission for the person in front of you to speak on behalf of a wider reality - which often means they’ll say what they wouldn’t say for themselves.
“What” as a default, not a technique. This isn’t about being careful with language. It’s about reorienting your curiosity. What happened? What mattered? What would you do differently? Each of those moves toward understanding. None of them invites a courtroom defence.
Questions to Sit With
Take one into your next meeting
When did you last ask a question in a meeting without already knowing the answer you were hoping for?
What would your team say about whether they feel genuinely heard in conversations with you?
Which question are you not asking - because you’re not sure you want to hear the answer?
If everyone in your organisation improved their questioning by 10%, what would actually change?
A Few Sources That Shaped This Thinking
Michael Bungay Stanier - The Coaching Habit
Tasha Eurich - Insight (2017)
David Rock - SCARF model, NeuroLeadership Institute
Trapnell & Campbell - Rumination and reflection in self-focused attention (1999)
If a question has been sitting with you - about your leadership, your team, or what comes next - I’d welcome a conversation. You can find me at calendly.com/katrin-7/time-to-connect-3.
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