Want to Be a Better Leader? Start Asking Better Questions
Because Being a Know-It-All Is Overrated
Picture this: You’re in a leadership meeting, and someone drops a problem on the table. Before anyone can blink, three people are racing to offer solutions, two are checking their phones, and one is already scheduling a follow-up meeting. Sound familiar? We’ve all been there—trapped in the leader’s curse of jumping to solutions faster than a caffeinated squirrel.
But here’s the plot twist: the best leaders aren’t the ones with all the answers. They’re the ones who know how to ask the questions that unlock better answers than they could have come up with alone. Think of it like being a detective in your own company’s story—except instead of looking for clues about who stole the office coffee maker, you’re uncovering insights that could transform your team.
The Hidden Power of Questions (And Why We Avoid Them)
Let’s be honest: asking questions can feel vulnerable. When you’re the leader, admitting you don’t know something goes against every instinct we’ve developed since that first time someone looked to us for answers. It’s like being the GPS that admits it needs directions—it feels wrong.
But here’s what actually happens when leaders ask good questions:
They turn monologues into dialogues. Instead of your team nodding along like bobbleheads, they become active participants in solving problems. It’s the difference between watching a movie and being in one.
They expose blind spots before they become crash sites. When you ask “What could go wrong?” or “What are we missing?”, you’re essentially creating an early warning system for your decisions. It’s like having a radar for potential face-plants.
They build trust faster than any team-building exercise involving trust falls (and with fewer insurance liability issues). When you genuinely ask for input, you’re saying, “Your brain is valuable to me.” People tend to appreciate that more than forced office fun.
The Art of Asking Questions That Actually Matter
Not all questions are created equal. Some questions are like cheap furniture—they look good in the showroom but fall apart the moment you try to use them. Here’s how to avoid the crappy furniture questions:
Instead of These Conversation Killers:
“Don’t you think we should...?” (Translation: Here’s what I think we should do, wrapped in a question mark)
“Why isn’t this done yet?” (Guaranteed to trigger fight-or-flight responses)
“Is everything okay?” (Too vague to be useful, too broad to be answered honestly)
Try These Conversation Starters:
“What would make this solution even better?”
“Walk me through what’s blocking progress right now.”
“What specific support do you need to move forward?”
The Question Framework That Changes Everything
Think of great questions like a good coffee brewing method—there’s a process to getting the best results:
Start with Context: “Before we dive in, help me understand what success looks like from your perspective.”
Explore the Landscape: “What opportunities are we not seeing?” “Who else should we be talking to about this?”
Drive to Action: “What’s the first small step we could take to test this?” “How will we know if this is working?”
Creating a Question-Friendly Culture (Without Turning Your Office Into a Philosophy Department)
Want to build a team that asks great questions? Start by modeling the behavior. Here’s how:
Make “I don’t know” Acceptable: When someone asks you something and you’re not sure, say, “That’s a great question—let’s figure it out together.” It’s more powerful than making up an answer or deflecting.
Reward the Asking: When someone asks a particularly insightful question, call it out: “That’s exactly the kind of thinking we need more of.”
Build Question Time Into Your Process: At the start of projects, have a dedicated session just for questions. Call it your “What If?” meeting if you want to get fancy about it.
The Daily Question Practice
Want to level up your question game? Here’s your daily workout plan:
Morning Question: Start team meetings with: “What’s one thing we should be thinking about differently?”
Midday Check: In one-on-ones: “What conversation should we be having that we’re not having?”
End-of-Day Reflection: Ask yourself: “What question should I have asked today but didn’t?”
The Bottom Line
Leadership isn’t about having all the answers—it’s about having the courage to ask the questions that lead to better answers. It’s about creating an environment where curiosity isn’t just welcomed, it’s expected.
So next time you feel that urge to jump in with a solution, pause. Take a breath. And ask yourself, “What question could I ask right now that would make this conversation more valuable?”
Because in the end, the quality of your leadership isn’t measured by the answers you give, but by the questions you ask that inspire others to find better answers than anyone could have found alone.
Remember: If you’re not feeling slightly uncomfortable with the questions you’re asking, you’re probably not asking the ones that matter most. And in leadership, just like in life, the most important discoveries often start with the questions we’re almost afraid to ask.
Want to level up your leadership questioning skills? Start by asking yourself this: “What’s one question I’ve been avoiding asking my team, and what’s really stopping me from asking it?”