Great entrepreneurship requires building trust. Maybe you’re in a sales meeting, pitching to investors, or trying to win a new client. You want them to see you as the perfect solution — so what do you do? You present yourself as flawless, capable, and ready for anything. Whatever they want, you say: “Yes, I can do that.”
But here’s what I’ve learned: That’s a mistake. The fastest way to build trust is not to convince people you’re perfect. It’s to be honest about where you’re not a fit at all.
I learned this when I began keynote speaking. Potential clients would describe what they wanted — and even when it wasn’t a fit for my expertise (which is helping people thrive in change), I’d try to sell them on me anyway. It never worked. Worse, I rarely heard from those people again.
Then I changed tactics. When it became clear I wasn’t the right speaker for someone’s event, I’d say: “My priority isn’t getting hired; it’s making sure you get exactly what you need. So I need to tell you, I’m not what you’re looking for.”
When I did that, something fascinating happened. Instead of ending the conversation, the honesty often deepened it. Sometimes, clients would appreciate my directness so much that they’d reshape their entire event around what I could offer. Other times, they’d ask me to recommend other speakers, which strengthened my network — and then the client would hire me the next year.
Why? Because by admitting I wasn’t perfect for every situation, I became the person they trusted most.
People don’t hire for perfect fits. They hire for trust. They want partners who will be straight with them, who won’t overpromise, and who won’t hide problems until it’s too late. And those people are hard to find.
I see this pattern everywhere. Have you ever asked a restaurant server for a recommendation? If they say, “everything is amazing,” they become untrustworthy. But if they tell you what’s good and what’s bad, they gain instant credibility. The same applies to leadership. When I interview successful entrepreneurs, the most compelling ones aren’t those who claim to never make mistakes. They’re the ones who can articulate their limitations while demonstrating their strengths. They’ll say things like, “I’m not great at the technical details, but I’m excellent at seeing the big picture.”
When you’re upfront about what you can’t do, you accomplish several things simultaneously. You show that you understand someone’s needs well enough to know when you’re not the right solution. You demonstrate that you care more about their success than your immediate gain. Most importantly, you prove that when you do claim to be a good fit, they can believe you.
Here’s how well this approach works: These days, when a client wants to hire me for a keynote, I still find some way to point out where I’m not a fit. For example, I was recently hired to speak to a credit union association. Then I told the organizers: “I just want to be upfront—I don’t know much about credit unions specifically, so I won’t be the most fluent on industry details.”
Their response: “That’s actually perfect, because we want someone with fresh eyes and an outside perspective.” By acknowledging my limitation, I highlighted why I was valuable to them. More importantly, they now trusted me more — because I’d shown a willingness to be honest, even at my own expense.
Remember, this isn’t about undermining yourself. It’s about building the foundation that all business relationships require. Trust is everything. And it’s earned by serving others before serving yourself.
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Great entrepreneurship requires building trust. Maybe you’re in a sales meeting, pitching to investors, or trying to win a new client. You want them to see you as the perfect solution — so what do you do? You present yourself as flawless, capable, and ready for anything. Whatever they want, you say: “Yes, I can do that.”
But here’s what I’ve learned: That’s a mistake. The fastest way to build trust is not to convince people you’re perfect. It’s to be honest about where you’re not a fit at all.
I learned this when I began keynote speaking. Potential clients would describe what they wanted — and even when it wasn’t a fit for my expertise (which is helping people thrive in change), I’d try to sell them on me anyway. It never worked. Worse, I rarely heard from those people again.
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