As coaches, our business is simple: catalyze results. If our clients aren’t achieving better, bigger, and more profitable outcomes than they would on their own, we’re falling short.
Fortunately, we have an arsenal of tools at our disposal. For example, we can:
- Offer perspective
- Provide context
- Help connect dots
- Articulate their vision
- Lend structure
- Guide them to a process
- Create peer accountability
- Model leadership
- Point out distinctions
- Relate experiences
- Shine a light on mistakes
- Suggest solutions
- Develop strategies
- And so much more.
These tools are invaluable, but there’s one that stands out: asking questions. Why? Because people love their own ideas. Questions engage their minds, trigger answers, and spark the kind of “aha” moments that lead to real action.
Here’s the kicker: the most productive questions are often the “dumb” ones. These are the questions most people are too shy—or too intimidated—to ask, even when things don’t make sense.
Why Dumb Questions Matter
“Dumb” questions challenge assumptions, clarify confusion, and uncover gaps in understanding. They’re especially important in areas where expertise can feel intimidating.
Take accounting and finance, for example. After 20 years as a CPA, banker, and investment banker, I’ve seen how often clients struggle to truly understand their numbers. Sure, most know their top line and bottom line, but concepts like direct costs and overhead? Not so much.
If I point this out too directly, it could backfire. CFOs or COOs might feel criticized, leading to defensiveness or even resentment. That’s why mastering the art of asking dumb questions is so important.
How to Ask Dumb Questions Well
- Gauge Capacity for Change: Not all clients are equally coachable. Some embrace change at scale, while others need a slower, more incremental approach. Great coaches know how to meet clients where they are.
- Balance Push and Patience: Following Gino Wickman’s advice to “go to the danger” is critical—but don’t be reckless. Push enough to create breakthroughs without damaging relationships or morale.
- Use Questions Strategically: Sparingly asking the right “dumb” question can help clients connect dots, articulate their vision, or rethink assumptions without feeling cornered.
- Know When to Let Go: Some clients may resist change entirely. In these cases, transitioning them to another coach might be the best course of action.
Structured conversations are key to making this process effective. The Mentor Meeting Model™ provides a framework for conducting meaningful coaching conversations, ensuring that the right questions—dumb or otherwise—are asked at the right time. By integrating these check-ins consistently, you help clients move beyond surface-level discussions and into deeper, more transformative insights.
Why This Matters
By asking questions—especially the “dumb” ones—you’re not just sharing expertise; you’re helping clients uncover their own insights, develop strategies, and build sustainable success.
So, the next time you hesitate to ask a “dumb” question, remember: it’s not about impressing your clients; it’s about empowering them to grow.
What’s your experience with asking “dumb” questions? Have they ever led to surprising breakthroughs or insights? I’d love to hear your story—drop a reply or share your thoughts in the comments!
P.S. Curious about what it takes to be a Summit OS Guide? Join my upcoming webinar to learn more!
