Great Leaders Ask Great Questions: 10 Scripts You Can Steal
Yesterday was Monday.
When you walked into work and said hello, how many times did you ask someone, “Did you have a good weekend?”
And what kind of answer did you get? Probably something like, “Yeah, it was good. How about you?”
Pretty surface-level, right? Not much real connection happening there.
The questions we ask matter — way more than we often realize. In fact, asking good questions is one of the most powerful (and most underused) leadership tools.
Recently, a client was getting ready to bring a big topic to her leadership team. As she told me about it, I asked, “How are you planning to facilitate the conversation?”
She paused and said, “Gosh, I don’t know. I hadn’t really thought about it.”
So we spent five quick minutes brainstorming a handful of open-ended questions she could ask to spark real dialogue and draw out her team’s ideas.
And honestly, I’m confident: those five minutes will completely change the quality of the conversation — and the outcome.
The best leaders aren’t the ones with all the answers.
They’re the ones who know how to unlock the brilliance already sitting in the room — just by asking the right questions.
When you ask a thoughtful, open-ended question, you don’t just gather information. You spark dialogue. You invite reflection. You open the door to new ideas and innovation.
Why Open-Ended Questions Matter
They spark critical thinking. Instead of yes/no answers, people reflect more deeply and connect new ideas.
They build trust. Open questions show that you value others' perspectives and experiences.
They encourage ownership. When people create their own solutions, commitment skyrockets.
They uncover hidden issues. Open questions surface concerns, hopes, and motivations you might otherwise miss.
In contrast, closed-ended questions ("Did you finish the report?") tend to limit conversations and encourage compliance over creativity.
But knowing how to ask better questions doesn’t always come naturally.
That’s why I’ve pulled together 10 ready-to-use scripts you can borrow, tweak, and make your own.
10 Leadership Question Scripts You Can Use Right Away
Instead of asking: "Did that meeting go well?"
Try: "What went well in the meeting, and what could have gone better?"
Instead of asking: "Do you need help?"
Try: "Where would support make the biggest difference for you right now?"
Instead of asking: "Is everything okay with the project?"
Try: "What’s feeling most on track, and where might you be hitting bumps?"
Instead of asking: "Do you agree with the decision?"
Try: "What’s your perspective on the decision and its impact?"
Instead of asking: "Will you meet the deadline?"
Try: "What potential obstacles do you foresee, and how can we plan for them?"
Instead of asking: "Are you clear on the goal?"
Try: "How would you describe our goal in your own words?"
Instead of asking: "Did you learn anything from that experience?"
Try: "What was your biggest takeaway from that experience?"
Instead of asking: "Was the client happy?"
Try: "How did the client respond, and what signals did you pick up from them?"
Instead of asking: "Are you feeling overwhelmed?"
Try: "What’s feeling most manageable right now, and what’s feeling heavy?"
Instead of asking: “Do you have any questions?”
Try: “What questions are coming up for you?”
Bonus Tip: Open-Ended Small Talk
This technique isn’t just for formal conversations. Even casual small talk gets better with open-ended questions:
Instead of asking: “Did you have a good weekend?”
Try: “What was one highlight from your weekend?” or “How did you recharge or relax over the weekend?”
4 Quick Tips for Using Open-Ended Questions Well
Start with “what” or “how.” These words naturally open up conversations. Avoid starting with “do,” “is,” or “why” (which can feel closed or make people defensive).
Be genuinely curious. People can sense when you're truly interested versus when you’re just checking a coaching box.
Pause after you ask. Silence isn’t awkward — it’s powerful. Give people space to think.
Follow up thoughtfully. Prompts like, “Tell me more about that,” or “What else?” can deepen the conversation.
Leadership Isn’t About Having the Right Answers
It’s about unlocking the right conversations.
Every question you ask either opens a door — or closes it.
When you choose better questions, you create a culture where people think more deeply, speak more honestly, and act with more ownership.
Better leadership doesn’t start with better answers.
It starts with better questions — and you’re just one conversation away.