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ATD Blog

The Top 5 Most Powerful Leadership Questions

Monday, February 1, 2021

For years, bestselling books, articles, and development programs have focused on how important it is for leaders to build trust, demonstrate vulnerability, and empower their teams. Leaders are taught to be curious, listen openly, and care for others. Compelling statistics show that leaders who coach and empower unlock potential and get better results.

At the most basic level, coaching is the ability to ask insightful, inquisitive, and perspective-shifting questions. Powerful questions are eye-opening, supportive, and even provocative. There’s no doubt in most leaders’ minds that asking questions and coaching have great value.

But then they get stuck. They find themselves in a challenging meeting or with a team member who is struggling. They falter and consider, “What question should I ask in this moment?”

Let’s look at five practical, workable, and powerful questions that leaders can ask their teams and when to use them. Don’t forget to make them your own.

1. What life experience has most shaped who you are?

This is a powerful way for team members to get to know one another, create connections, and build trust. Sharing personal stories can foster empathy, understanding, and relationships. A new appreciation and understanding of where others are coming from can help virtual teams or those struggling with conflict.

Variation: Who has been the greatest influence in your life? Why?

2. What makes it all worthwhile to you?

As you build your relationship with your employees, it’s important to understand what meaning they derive from their work, what they see as their purpose, and what motivates them. With this shared understanding, it’s easier to inspire, develop, and empower others in a meaningful way.


Variation: Why do you do what you do?

3. Where do you have the most impact?

We each contribute in a unique way to our teams and to our organization. Sometimes we don’t stop to consider where we have the greatest impact and why. Asking this question helps your employees look at where they have impact as well as where they want to have even more of it. This knowledge can help you tap into their natural strengths, aspirations, and potential in a new way.

Variation: What do you want to build or create in your lifetime?

4. What stands between you and where you want to go?

This question is challenging to ask and answer. It’s most powerful when someone is stuck. They may be struggling with an interpersonal issue with a colleague, a project-related challenge, or the direction of their career. Talking through the vision for the future and what might be getting in the way is a great start.


Variation: What are you avoiding doing that you know you should do?

5. How are you? How are you really?

We are asked multiple times a day how we are doing. The default is often “fine.” There is usually more below the surface that we don’t share with others for various reasons. We may be feeling stressed, anxious, overwhelmed, or burned out. We may also be enthusiastic, optimistic, and excited but don’t see an opening to share how we are feeling. Learning what’s really going on helps a leader address issues before they get too far as well as tap into positive energy that could make a big difference to the team and the organization.

Don’t Forget the Obstacles

Even when leaders have a curious mindset, are comfortable being vulnerable, and have a toolbox of great questions, things can get in the way. When we want to look good, be right, or be in control above all else, we don’t let down our guard to be open, vulnerable, or involve others. It’s hard to be curious when the toxic trio has you in its grip.

Our Charge as Leadership Development Professionals

We can help our leaders build the confidence to ask powerful questions, try again if they fail, and use a mindset of curiosity to develop and empower others. Learn more at

About the Author

Katy is a managing partner at Leader Success Inc. and has over 25 years of experience as a leadership development executive. She has worked with leading organizations across industries from start-ups to large, global organizations. Leader Success offers virtual and in person team and leadership programs with a focus on coaching, feedback, communication, strategic thinking, managing inclusively, leading virtual teams, and career development. Leader Success has facilitators, consultants, and coaches across the globe. Katy has a BA in International Relations from Duke University and an MBA from UC Berkeley’s Haas School of Business.

Katy is a Fulbright Scholar. She is a certified Executive Coach through the International Coaches Federation.

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