How to be a great leader: 31 leadership conversation questions

We are all leaders in our own ways.

And if you want to accomplish anything bigger in life, you will end up working with leaders or taking up leadership. 

Now, if you told that to the high school Ian… I’d have run away in horror! 

Being the shy, anxious kid, I almost always preferred doing my own thing, vs. being in teams. 

Over time however, I fell into leadership as I started one ambitious project after another, which meant that I had to learn how to work with others and lead teams. It was pretty much a baptism by fire. Here’s what a former boss said about me:

“Ian is a proven leader and innovative thinker: he has the kind of profile that would rival people 10 years his senior…His efforts have played a large role in our success.”

— Kyle Hill, Teach For Canada cofounder, former Boston Consulting Group project leader

These questions will help you explore how to become a better leader, and also how to work with one. 

If you’re talking to a student 

1. Who’s a leader you admire in school?
2. Which classmate do you consider a leader? 
3. Which teacher do you consider a leader? 
4. Who’s a leader you admire in life?
5. How have you motivated your classmates or schoolmates? 
6.  Tell me about a moment when you motivated your classmates to achieve something. 
7. If you were the school principal/university president, what’s the first thing you would change? (What wouldn’t you change?)

If you’re talking to an employee 

1. Do you consider yourself a leader? Why or why not? 
2. How have you shown leadership on a project/in your role?
3. How can I support you in growing your leadership skills? 
4. What makes someone a great leader?
5. What’s the difference between a bad and a good leader?
6. Who was the best leader you worked with and why? 
7. What leadership style makes you more motivated? What leadership style makes you less motivated? 
8. What feedback do you have for me as a leader? 
9. What’s one thing you appreciate about my leadership?
10. What’s one thing you’d change about my leadership? 

If you’re talking to your manager/boss 

1. How can I grow my leadership skills? 
2. If I were to take up leadership in the business, what advice do you have for me?
3. What has helped you become a better leader? 
4. How would you describe your leadership style?
5. What are your three values as a leader? 
6. What’s the one quality all great leaders have? 
7. What’s the one mistake most leaders make? 
8. Which leader do you consider your role model? How has s/he influenced you? 

If you’re talking to a family member 

1. Which family member do you consider the leader of the family? 
2. What does family leadership mean to you? 
3. How have you supported the family? // How do you want to support the family? 
4. What support do you need from the family to achieve your goals? 
5. What are three values that our family should have?
6. What should our family stand for or not stand for?

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