Questions
Most leaders think their job is to give direction. The best ones know their job is to stay curious long enough to see clearly. Questions are how we fight arrogance and drift. They’re how we stay awake. The right question cracks through the surface of certainty and lets light in. If your leadership is getting stale, you don’t need another framework — you need a better question.
Patterns I See
Premature clarity: Leaders lock onto answers too fast, mistaking decisiveness for wisdom.
Intellectual laziness: The hard questions go unasked because they’d require change.
Question fatigue: Teams stop asking because they know curiosity isn’t rewarded.
What Leaders Miss
The point of a question isn’t to get an answer — it’s to expand awareness.
Good questions act like chisels. They break assumptions apart so we can see what’s really inside.
The best leaders I know are question collectors. They hunt for the ones that cut through noise and open new paths. They understand that “why?” is the doorway to meaning, and “what if?” is the doorway to imagination.
A weak question looks backward. A strong one leans into the unknown.
Working With It
Use questions as mirrors. Ask what they reveal about your blind spots.
Trade speed for substance. A pause before you answer is the birthplace of discernment.
Curate your core questions. Every season of life and work has a handful worth carrying — the ones that keep you honest and humble.
Lead with curiosity in the room. Don’t just challenge others — invite them to challenge you.
Questions Worth Asking
What question am I avoiding because I already know the answer will cost me something?
What if the problem isn’t “out there,” but in how I’ve been framing it?
What question would make this conversation worth having?
What would happen if I stopped pretending to know?
Field Truth
Answers close loops. Questions open doors.
Stay curious long enough, and the right doors appear.
