10 Questions Every Leader Should Ask Themselves

Leadership development isn't just something you do in workshops or coaching sessions. It's a practice. A daily, ongoing examination of how you're showing up, what you're creating for the people around you, and whether you're living the values you say you hold.

These ten questions are the ones I come back to in my own work and invite the leaders I coach to sit with regularly. They're not easy. That's the point.

1. How do people feel after they've been with me?

Not what they think of you. How do they feel. Energized or depleted? Seen or invisible? Safe or guarded? The answer to this question tells you more about your leadership than any 360 feedback ever will.

2. What am I pretending not to know?

Every leader has something they're avoiding. A performance conversation. A strategic problem. A relationship that's eroding. Naming it is the first step to doing something about it.

3. Am I the same person at work and at home?

Not identical — context matters. But are your values, your humor, your humanity present in both places? If you're a completely different person at work, something worth examining is happening.

4. When did I last change my mind because of something someone else said?

If you can't remember, that's data. Leaders who can't be changed by what they hear aren't actually leading — they're just directing. Genuine curiosity and intellectual humility are leadership superpowers.

5. Am I developing the people around me or just using them?

Are the people on your team growing? Are they building skills, taking on new challenges, being stretched in ways that serve their development — not just your deliverables? The best leaders leave people more capable than they found them.

6. What behavior am I tolerating that I shouldn't be?

Tolerating bad behavior — even once — sets a new floor for what's acceptable. What are you allowing that's out of alignment with your values? What conversation have you been putting off?

7. How am I taking care of myself?

Not as a lifestyle question. As a leadership question. You cannot bring clarity, courage, and presence to your team if you're running on empty. Your wellbeing is a leadership responsibility, not a personal indulgence.

8. What story am I telling myself about this situation?

Our brains fill in gaps with stories. Most of the time those stories are not facts — they're interpretations. What assumptions are you carrying about your team, your organization, or yourself that might not be true?

9. Am I leading with fear or with values?

Fear-based leadership is pervasive and often invisible to the leaders practicing it. Are your decisions driven by what you believe is right — or by what you're afraid of? The distinction shapes everything about your culture.

10. What would I do if I weren't afraid?

This is the question that cuts through almost everything. The answer usually points directly at exactly where your leadership needs to grow.

These questions don't have permanent answers. They're meant to be revisited — weekly, monthly, in the hard moments and the quiet ones. If one of them landed particularly hard, that's probably exactly where to start. I'd love to be part of that work.