How to ask great questions

'Stupid' questions

Now, let’s talk about stupid questions. And before you worry—no, I don’t actually mean questions that are dumb. Quite the opposite.

A “stupid” question is often the smartest one in the room. It’s the one that cuts through jargon, gets rid of assumptions, and makes sure everyone understands what’s going on.
Imagine you’re in a meeting, and someone rattles off an acronym or a technical term that flies right over your head. You could sit there and nod along, hoping it makes sense later, or you could say:

"Hang on—what does that actually mean in practice?"

Or:

"Can you break that down for me?"

I did this the other day. I was talking to someone who mentioned ‘DE&IB’. Now, I know DE&I—Diversity, Equity, and Inclusion—but I’d never heard the B on the end before! I almost let it slide, thinking, "I’ll Google that later." But then I thought, no—if I don’t know, others probably don’t either.

So I asked: "What’s the B stand for?" And do you know what? Even the person who said it had to stop and think.
Turns out, it stood for ‘Belonging’, but it wasn’t a widely used term—just something they’d started saying in their organisation.

That’s the power of a so-called stupid question. It stops the room from running on assumptions. And when you’re the one brave enough to ask, everyone else breathes a sigh of relief because they were probably wondering the same thing.

Coaching questions

Finally, we’ve got coaching questions. These are the ones that help people think more deeply, reflect on their own decisions, and take ownership of a problem. Let’s say someone comes to you and says, "What should I do?"
It’s tempting to just give them the answer, isn’t it? But the smarter move is to help people work it out for themselves.
Instead, try flipping it around:

"What do you think you should do?"

Or:

"If you were giving advice to someone else in this situation, what would you say?"

These kinds of questions get people thinking for themselves. They stop waiting for someone else to solve the problem and start working through it on their own. And that’s what builds real confidence and independence in your team.
You can also use coaching questions to encourage reflection. Questions like:

"What would need to happen for this to be a success?"

Or:

"What’s one small change you could make today that would have a big impact?"

These don’t just get people answering in the moment—they get them thinking, which is exactly what you want.

How to ask great questions - The complete list!

Asking thoughtful questions helps you stand out, build confidence, and sharpen communication skills. The right question at the right time can unlock valuable insights, deepen conversations, and position you as an engaged and perceptive communicator. Use this guide to structure impactful discussions in business and leadership settings.

1. Starter/Warm-up questions

(Break the ice, create rapport, and set a positive tone.)

These questions are ideal at the start of a conversation, whether in a networking setting, a business meeting, or an informal catch-up. They help build a connection before diving into more serious topics. A warm-up question signals that you are genuinely interested in the person, not just the transaction. They work well with new contacts, senior leaders, or colleagues you haven’t seen in a while. Keep them light, positive, and tailored to the person’s recent work or achievements.

• “What’s been the highlight of your year so far?”
• “I read about your recent project—what was the most rewarding part of it?”
• “How did you get into this field?”
• “What’s keeping you busy at the moment?”

2. Data point questions

(Gather facts and key details to build a strong understanding.)

These questions help you uncover specific details that can inform decision-making, strategy discussions, or business reports. They are best used in formal meetings, stakeholder interviews, or analytical discussions where factual clarity is required. They work well when engaging with finance teams, project managers, analysts, or subject matter experts. Be direct and precise, and ensure the question is relevant to the conversation.

• “What’s the biggest challenge your team faced last quarter?”
• “How has the new strategy affected your KPIs?”
• “What percentage of your customers have adopted the new system?”
• “Can you share any stats on how this has improved performance?”

3. Opinion-based questions

(Encourage insights and perspective on a situation.)

Use these when you want to understand how someone thinks or feels about a particular issue. These are particularly useful in leadership meetings, panel discussions, and performance reviews. They work well with decision-makers, industry experts, or team members providing feedback. Approach them with curiosity rather than an agenda, allowing the other person to share their honest thoughts.

• “What’s your take on the recent changes in the industry?”
• “How do you think this decision will impact the wider team?”
• “Do you see this as a short-term fix or a long-term solution?”
• “If you could change one thing about how this is being handled, what would it be?”

4. Outlook-based questions

(Gain insights into predictions and future trends.)

These questions help uncover strategic thinking, long-term goals, and industry trends. They are particularly useful in leadership discussions, planning meetings, and industry panels where foresight is required. They work well with executives, policymakers, or anyone responsible for shaping the future of a business. Ask these when looking for direction, risk assessment, or innovation insights.

• “Where do you see this market heading in the next five years?”
• “What’s your biggest hope for the future of this project?”
• “If this trend continues, what will the impact be on your customers?”
• “How are you preparing for the next stage of growth?”

5. Supplementary/Follow-up questions

(Encourage deeper explanations and uncover more detail.)

Follow-ups are critical for getting richer insights and avoiding surface-level responses. They are particularly effective in interviews, negotiations, and any conversation where detail matters. These questions work well with clients, stakeholders, and senior leaders who may initially provide broad answers. Use them to demonstrate active listening and uncover key information that wasn’t shared in the first response.

• “That’s interesting—you mentioned X. How does that compare to last year?”
• “Could you expand on that point a little?”
• “You talked about a challenge earlier. How did you overcome it?”
• “What were the key factors that influenced that decision?”

6. Closed questions (Use sparingly, but follow up!)

(Useful for quick confirmation, but should be followed by an open-ended question.)

Closed questions can clarify key points quickly but should rarely be left hanging. They work well in meetings, sales calls, and operational discussions where a simple yes or no is needed before diving deeper. Be prepared to ask an open-ended follow-up to keep the conversation going.

• “Did that initiative increase engagement as expected?” (Follow-up: What do you think made it successful or not?)
• “Has the new policy made a noticeable difference?” (Follow-up: In what ways?)
• “Do you think this will be a recurring issue?” (Follow-up: What makes you say that?)
• “Was that change driven by internal or external factors?” (Follow-up: What were the key influences?)

7. Open questions

(Encourage conversation and insight-sharing.)

These questions create space for discussion, making them valuable in coaching, performance reviews, and leadership development conversations. They are particularly useful when speaking with employees, peers, or mentees who need encouragement to express their thoughts. Keep them broad enough to allow freedom of expression but focused enough to guide a productive discussion.

• “What surprised you most about the outcome of that decision?”
• “How has this experience shaped your approach to leadership?”
• “What’s been the biggest lesson you’ve learned from this project?”
• “How do you think your team feels about this change?”

8. ‘Stupid’ questions (Actually very useful!)

(Ask for clarification to ensure understanding—great for cutting through jargon.)

These are particularly valuable in technical discussions, financial reviews, and high-stakes meetings where clarity is essential. They work well with subject matter experts, consultants, and executives who may assume knowledge that others do not have. These questions are not actually ‘stupid’—they help remove ambiguity and make sure everyone is on the same page.

• “I hear people use that term a lot—what does it actually mean in practice?”
• “Can you explain that as if I were completely new to the industry?”
• “I’m not quite following—could you break that down for me?”
• “Why is that important? I want to make sure I understand fully.”

9. Get-Out-of-Jail questions

(For when you need to buy time or redirect the conversation.)

These are excellent for panel discussions, live Q&As, or situations where you’re caught off guard. They give you time to think or steer the conversation in a direction where you feel more comfortable. Use them when speaking with journalists, senior leaders, or during high-pressure situations where you need to regain control of the discussion.

• “Can you walk me through your thought process on that?”
• “That’s really interesting—how did you come to that conclusion?”
• “Could you give an example of what that looks like in action?”
• “What’s the ‘so what’ of this situation?” (Encourages people to explain why it matters.)

10. Coaching questions

(Encourage deeper thinking and reflection.)

These are most effective in mentoring sessions, leadership coaching, and team development meetings. They work well when engaging with emerging leaders, employees in transition, or executives reflecting on strategic decisions. Use them to encourage self-awareness, accountability, and a proactive mindset.

• “What would need to happen for this to be a success?”
• “What’s within your control that could improve this situation?”
• “If you were giving advice to someone else in this position, what would you say?”
• “What’s one small change that could have the biggest impact?”

Key takeaways

• Use open questions to spark meaningful conversations.
• Follow up on closed questions to dig deeper.
• Clarifying questions can build understanding and show engagement.
• Opinion and outlook-based questions help shape insightful discussions.
• Coaching questions encourage problem-solving and reflection.

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