As leaders, we talk a lot about the importance of listening—but how often do we reflect on how we listen? If you've ever wondered how to take your listening skills to the next level, you're not alone. I’ve spent years studying leadership, and one thing is crystal clear: great listeners ask great questions.

Today, I’m excited to share five listening questions that can transform not just how you communicate but how others perceive your leadership. These questions aren’t just about gathering information; they’re tools for building relationships, understanding others on a deeper level, and inspiring meaningful conversations.

If you’ve ever felt like your conversations are hitting a wall, or you’re struggling to show someone you really care, these questions will help. Let’s dive into how you can use them to become not only a better listener but a better leader too.

Five Great Listening Questions

1. How does that make you feel?

When someone shares something with you, this question helps uncover their emotions and shows that you care about their perspective. Emotions drive many decisions, and understanding how someone feels gives you valuable insights that go beyond surface-level facts.

2. What do you think about that?

While the first question taps into feelings, this one zeroes in on thoughts. It's perfect for logical thinkers or when you’re looking for analytical insights. Both types of questions—feeling-based and thinking-based—serve different purposes, and using them intentionally can dramatically improve your communication.

3. What else?

Sometimes, the best way to encourage someone to share more is to simply ask for it. Whether you say, “What else?” or “Tell me more,” this simple phrase opens the door for deeper insights and helps the other person feel truly heard.

4. What is the most important part of this?

In every conversation, there’s usually a core idea or issue that matters most to the other person. This question helps uncover their priorities and ensures you’re focusing on what they value most.

5. What have I missed?

Asking this shows humility and a genuine desire to fully understand. By inviting the other person to point out gaps in your understanding, you not only learn more but also demonstrate respect for their perspective.

Bonus Questions for Deeper Engagement

Beyond these five, there are a couple of other tools I use to elevate my listening:

  • Paraphrasing: Try summarizing what you’ve heard with, “What I’ve heard you say so far is…” followed by, “Is that correct?” This validates their thoughts and gives them a chance to clarify.
  • How can I support you? A simple yet powerful question that turns listening into action. It’s particularly impactful as a leader or friend and shows you’re ready to help.

Why These Questions Matter

The ability to listen isn’t just about staying quiet while someone else speaks. It’s about asking questions that show you’re engaged, curious, and invested in understanding their perspective. These questions aren’t just techniques; they’re bridges to better relationships and more effective leadership.

So here’s my challenge for you: pick one or two of these questions and start using them this week. Watch how they change your conversations—and your connections with others.

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Kevin Eikenberry is a recognized world expert on leadership development and learning and is the Chief Potential Officer of The Kevin Eikenberry Group. He has spent over 30 years helping organizations across North America, and leaders from around the world, on leadership, learning, teams and teamwork, communication and more.

Twice he has been named by Inc.com as one of the Top 100 Leadership and Management Experts in the World and 100 Great Leadership Speakers for Your Next Conference. The American Management Association named him a “Leaders to Watch” and he has been twice named as one of the World's Top 30 Leadership Professionals by Global Gurus. Top Sales World has named him a Top Sales & Marketing Influencer several times, and his blog has been named on many “best of” lists. LeadersHum has named him one of the 200 Biggest Voices in Leadership in 2023.

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