Leadership Is the Practice of Curiosity and the Art of Asking Better Questions

It’s well known that listening is the most valuable tool in a leader's toolbox. But over the years I've started to wonder if we've been teaching it the wrong way. We tell leaders to "listen more", but we spend far less time teaching them how to ask the kinds of questions that make people feel heard in the first place. Because good listening doesn't begin with our ears, it begins with our curiosity.

My background is in psychology and counselling, where listening isn't simply a communication skill, it's part of the intervention itself. One story I've always found fascinating is that Sigmund Freud rarely took notes during therapy sessions. His belief was that writing distracted him from being fully present. Whether or not you agree with all of Freud's theories, I think there's something leaders can learn from the idea that presence changes conversations.

What I've learnt after years of leading teams, is that listening isn't enough. If all we do is quietly absorb information, we'll only hear what people are saying. But if we're genuinely curious, we'll discover what they really mean. Good listening enables better questions and curiosity shows up in the questions we ask. Curiosity and better questions tests our assumptions and fills knowledge gaps.

So are you looking for better questions to add to your leadership toolbox? These are the questions I come back to again and again because they invite people to think, to reflect and to tell you what really matters.

1. “Tell me about your role” (I always ask this when meeting someone for the first time. I'm not asking about their job title, I want to understand how they experience their work. This demonstrates genuine interest and creates connection)

2. “Can you tell me more about that?” (It sounds simple, but it's one of the most powerful questions I know. People will often give us the headline first so this question gives them permission to tell the story underneath.)

3. “What do you think the answer/solution is?” (One of the biggest lessons my career has taught me is that the people closest to the problem are usually closest to the solution. Leaders don't need to have all the answers, they need to create the conditions where the best answers can emerge.)

4. “How does that land with you?” OR “What are your thoughts on this?” (This is a curious and collaborative approach to check understanding)

5. “What is the best way to support you right now?” (this is my favourite and creates the opportunity for people to communicate their needs to their leader)

Leadership isn't about having the best answers, it's about creating the conditions for better conversations. And those conversations rarely begin with advice, they begin with curiosity and a question.

If you'd like to build more meaningful one-to-one conversations with your team, I've created a free guide through Gray Matter Training & Consulting. You can download it from this page

1_1 conversation guide.PDF

Download PDF • 117KB

.