Top 20 Great Questions Leaders Ask

Great results begin with great questions. We compiled the top 20 questions to help you seek understanding in leadership.

Experts know the questions to ask to get to the heart of the challenge and opportunity. When my team at Inspiring HR consults with our small business clients, they are trained to identify the root challenges facing our clients’ companies, so we can help them fix those challenges. 

A key tool we use daily with our clients is asking them great questions to help them seek understanding within their leadership. 

In the book, Change Your Questions. Change Your Life, the author writes, “Questions that we ask either expand our mindsets, opening us to exciting new possibilities, or constrict our mindsets, limiting our choices.”

Recently, I brainstormed with several of my team members about the kinds of questions they recommend leaders ask to their team members and of themselves.

I’ve summarized our top 20 questions to help you seek understanding in leadership within your company. Pick a few questions to ask yourself and others in your company. Make it a weekly habit to challenge yourself to ask better questions. As we say at Inspiring HR, “Great Questions Equal Great Results.”

Great Questions Leaders Ask

Questions to Ask Your Team

1. Are we working on the right problems?
2. Which team members are underperforming, and how can we help them do better?
3. What’s a common skill gap we could improve?
4. Which markets, partners, clients, or other opportunities can add significant value to our business?
5. What areas of training or support do we need? 
6. What are your biggest obstacles and barriers to success? What are your plans to deal with them, and what do you need from me?
7. What areas of training or support do we need? 
8. What’s our /your biggest risk, and how do we mitigate it?
9. Is this meeting necessary?
10. What are your biggest obstacles and barriers to success? What are your plans to deal with them, and what do you need from me?
11. How will this decision impact (individual, team, business unit, competitive advantage, brand perception, customer satisfaction, etc.)?
12. What are people thinking but afraid to express?
13. What makes our culture unique, and how do we protect that?
14. What if we did nothing at all, what would happen?
15. What’s your greatest current frustration, and how can I help you with that?

Questions to Ask Yourself

1. What do I love about leading? What do I not love? What do I think I need to lead better?
2. What did I learn this week that I can apply to my work next week?
3. What’s our biggest risk, and how do I mitigate it?
4. What does leadership mean to me? How does it look and feel like?
5. What am I doing daily to build other leaders?

Have a question about your HR plan and strategy? At Inspiring HR, we uncomplicate HR and empower small businesses. Contact us today for a consultation to see how we can help you!