08/23/2026
Early in my career, I spent 22 years in sales — and if there's one thing sales teaches you, it's the power of asking the right questions. Great salespeople don't lead with answers. They lead with curiosity. They ask, they listen, and they let the truth of the conversation do the work.
But here's what I've learned in the years since — first as a leader across corporate, government, and healthcare organizations, and now as an executive coach: asking questions of others is one thing. Asking honest questions of yourself is something else entirely.
It requires a level of brutal honesty that most people quietly resist. Because when you ask yourself the hard questions — really ask, and really listen to the answers — you can't unsee what you find. And that means you have to do something about it.
One of the first things I do with every new coaching client is walk them through exactly that process. Not trick questions. Not interview questions. Just honest, direct questions about where they are, what they want, and how they're leading right now.
You'd be surprised how many accomplished, talented, driven leaders struggle to answer them — not because they don't care, but because the relentless pace of leadership rarely leaves room for the kind of honest reflection these questions require.
In this article, I'm sharing those five questions with you. They're the foundation of the Listen & Learn stage of my LEAP Framework™ — and they're worth sitting with whether you're working with a coach or not. Some of them will feel easy. Others might surface something you've been quietly avoiding.
Either way, what you discover will be worth it.
Part of The Envision Series | The LEAP Framework™ | Bentley Consulting Group If you've been following this series, you know we spent the last three posts going deep on Stage 1 of the LEAP Framework™ — Listen & Learn. Now we move to Stage 2: Envision.
