4 Questions Great Leaders Ask Themselves

I’ve been working with leaders and organizations for many years now. I’ve worked with CEOs of large tech companies and small start ups. I’ve also worked with leaders of faith-based organizations and churches. I’ve seen organizations that have grown to adapt to changing environments, and I’ve seen organizations that have stagnated and declined when faced with the same challenges. So what is the difference between a leader who grows through changes and challenges and one who doesn't? The answer - in a word – is curiosity. 

Great leaders ask great questions. They aren’t afraid to become uncomfortable, learn something new, or try something different to grow their organization or personal leadership skills.  

Here are some questions every great leader needs to be asking regularly:

1. What don’t I know?

As a leader climbs up the organizational chart, they tend to become more and more isolated from the rest of the team. They often only have 1-2 direct reports, so all their information is filtered through those people. Great leaders take time to visit one-on-one with team members who are much farther down the org chart. They ask hard questions, and listen carefully for the answers. Some even initiate an anonymous survey that helps team members speak openly about the challenges they are facing or ideas they have make improvements.

Great leaders are always trying to shrink their blind spots and expand their vision.

Ask yourself: What don’t I know about the people I work with? What about the current status of our organization? What do I need to know about the people that our organization serves?

2. Who do I need to listen to?

As a leader, listening to outside voices can sometimes cause organizational drift and confusion among the staff. However, leaders who refuse to listen to anyone other than those they agree with, or only to trusted voices from the past, will find themselves stuck. Of course, for pastors and any Christ-follower, the most important voice is God’s and that voice is heard most clearly in the Bible. But what about voices of those who can help us think differently about how we can innovate in our work?

As leaders age with their organizations, the less willing they to listen to outside voices or consider new ideas. Great leaders are always asking about to whom they should be listening in order to stay sharp.

Ask yourself: Do I need to get out of the office listen to our staff more? Is there a conference I need to attend? A course I need to take? A podcast I need to subscribe to?

3. What do I need to change?

Great leaders understand that change is not optional – neither for their organizations or themselves. They know that in order for their organization to continue to make an impact, its methods and approaches will need to change over time. Perhaps it will be their leadership style, staff structure, ministry approach or style. The world is changing, and great leaders will adapt to the change to be as effective as possible.

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Ask yourself: What do I need to change? What do we need to change? What needs to stay the same?  

4. What am I afraid of?

This question is huge! I’ve met leaders who are willing to listen to new ideas and be challenged in their thinking, but when it comes to tangibly making those changes, they stop short. Why? They are afraid.

Great leaders are incredibly self-aware because they are insatiably curious about themselves. They want to know why they do the things they do and why they don’t take action even when they know they should. Generally this comes down to a root fear that they have often hidden or disguised. Great leaders will name their fears in order to face them and overcome them.

Ask yourself: What am I afraid of? Is it a fear of failure? Of the unknown? Of feeling uncomfortable or incompetent?

Great leaders are insatiably curious. They are curious about themselves, their organization, their constituents, and the world. They ask hard questions and are comfortable being uncomfortable because they know it will stretch them and make them better.

What are some questions that you’ve asked in the past to help you as a leader?