In my previous article, we explored how wisdom grows when leaders truly listen. But what does that look like in practice? A proverb reminds us, “A person’s thoughts are like water in a deep well, but someone with insight can draw them out.” The best leaders do this not by talking more but by asking better questions.
One of the clearest signs of a skilled listener is the ability to ask open-ended questions. These questions invite more than a quick “yes” or “no”. Instead of asking, “Did you finish the report?” try, “What progress have you made on the report?” or “What’s helping or slowing progress right now?” That small shift moves the conversation from ticking boxes to understanding context.
Many leaders are taught to ask “powerful questions”. But these can backfire. Ask, “What would success look like?” and you assume success is the goal. Ask, “What did you like best?” and you assume they liked something. People sense these assumptions. And they hold back.
So how can we ask questions that open space rather than close it?
Clean Language can help. Instead of inserting your own words and assumptions, you use theirs. If someone says, “The meeting was frustrating”, you ask, “What kind of frustrating?” or “What happens when it feels frustrating?” It might sound odd at first, but it keeps you from interpreting their experience through your lens.
Listening well isn’t about words alone. Be genuinely curious without pushing your agenda. Be patient. Don’t rush to solutions. Be present without judgment. When leaders do this, people open up. Trust builds and deeper insights follow.
Of course, not every conversation needs a deep dive. Sometimes a simple “Tell me more about that”, “What else comes to mind?” or “How did that affect you?” is enough. The key is being genuine. People can tell when you’re asking from a script versus when you’re fully present.
To strengthen your leadership listening:
- Ask with curiosity: seek to understand before evaluating.
- Stay neutral: avoid leading questions or assumptions.
- Reflect back: use their own words to confirm what you’ve heard.
Great questions aren’t about extracting information. They create safe spaces for people to think, reflect and grow. When you give someone your full attention and listen deeply, you offer something rare. Leaders who do this well don’t just gather facts. They build wisdom, trust, and stronger teams.
p.s. Want to take your listening and leadership skills to the next level? Join a Kingdom Factor Cohort (KFC), a peer advisory group for Christian CEOs, executives and business leaders to practice asking questions, listening deeply, and growing wisdom together. DM me ‘KFC’ if you’d like to learn more.
Inspired by Rick Warren.