The 10 Executive questions that change everything
(If you dare to answer them honestly)
Most executive teams don’t fail because of strategy. They fail because of what they avoid.
- Avoiding difficult conversations.
- Avoiding uncomfortable truths.
- Avoiding the decisions that actually matter.
After 35+ years of having (executive) leadership roles myself, and having coached managers and executives, as well as their teams, I’ve learned this:
One sharp question at the right moment can shift an entire leadership team.
Here are the 10 questions I use with senior leaders — questions that cut through noise, expose blind spots, and accelerate real transformation.
- These are not “coaching questions.”
- They are leadership questions.
- And they require courage.
10 provoking questions that change executive teams:
1. What are we pretending not to see?
Every organization has an elephant in the room. Naming it is the first act of leadership.
2. If nothing changes, what breaks first?
Pressure reveals where your system is weakest. This question brings the cracks into daylight.
3. What decision are you avoiding — and why?
Executives don’t lack knowledge; they lack movement. The avoidance is the problem.
4. What would your team say you’re not listening to?
Leadership is not what you say, it’s what your team experiences.
5. If your team behaved exactly like you this week, would performance go up or down?
Your behavior is the culture. This one hurts, and that’s why it works.
6. What have you stopped caring about that you should care about?
Fatigue creates blind spots. Re-engage where it matters.
7. What truth is no one in this room willing to say out loud?
Alignment doesn’t come from politeness. It comes from honesty.
8. What would your successor stop doing on day one?
Leaders rarely realize how many legacy habits they protect.
9. What is the real problem — not the one you’re comfortable discussing?
Executives often treat symptoms because symptoms feel safe. Real leadership goes deeper.
10. What must look different 90 days from now — and what must you change to make it happen?
No more hiding behind the team, the system, or the strategy. Accountability starts with you.
Why these questions matter
Because leadership is not about having answers. It’s about creating clarity, inviting truth, and accelerating action.
These 10 questions help executives:
- see reality sooner,
- act with more confidence,
- build trust faster,
- make better decisions, and
- align their teams around what truly matters.
If you want to grow as a leader — start by asking better questions.
And then, answer them honestly.
If you are interested in working together, let me know
