You Can’t Outsource Conviction: Why Serious Buyers Stop Asking for Permission

“Is this a good deal?”

We hear this question constantly—often from buyers who are already under LOI. These are smart, capable people. They’ve built a model. They’ve pressure-tested downside scenarios. They’ve negotiated a seller note. Maybe they’ve even gotten verbal interest from lenders and investors. And yet, they’re still asking for a final verdict—some stamp of approval that makes them feel like it’s safe to say “I’m in.”

We get it. Buying a business is a high-stakes decision. You’re committing years of your life and potentially hundreds of thousands of dollars. It’s tempting to look around and ask someone—anyone—“Do you think I’m doing the right thing?”

But here’s the reality: you can’t outsource conviction. At the end of the day, it’s your deal. Your risk. Your reward. Your name on the signature line. No amount of external validation is going to make that decision for you—and if you wait for consensus, you’ll either lose the deal or end up buying something so “safe” that it has no upside left.

The Psychology Behind the Question

When someone asks, “Is this a good deal?” they’re often not looking for analysis. They already have that. What they want is permission—someone to say, “Yes, you’re doing it right.” It’s a normal human response to uncertainty. But it’s also a dangerous one, because it shifts responsibility away from the buyer and toward an advisor, investor, or mentor who doesn’t have full context—and won’t be there on Day 100 when reality hits.

Let’s say the deal underwrites to a 65% return for you and your investors. You believe in the industry. You’ve met the team. You’ve uncovered warts but nothing fatal. Your gut says go. So what happens if someone else says, “Eh, I’ve seen better deals”? Do you walk? Do you renegotiate? Do you second-guess everything you thought you believed?

Conviction doesn’t mean arrogance. It means ownership.

What to Ask Instead

If you want to build conviction, stop asking for permission and start asking better questions:

• “What am I missing?” – Invite people to challenge your assumptions.
• “Where would you poke holes in this deal?” – Get help identifying blind spots.
• “What’s the one thing that would make you walk away?” – Pressure test the risk profile.
• “What would make this deal more resilient?” – Sharpen your execution plan.

Those questions get you feedback, not approval. That’s what you should be after.

Strong Opinions, Loosely Held

Conviction doesn’t mean ignoring advice. It means doing your own thinking. Have strong opinions, loosely held. Be ready to adjust if someone gives you new information. But don’t let someone else’s hesitation become your excuse to freeze. If your gut says go, and your diligence checks out, then own the decision.

Because in the end, no one else is going to run this business but you. You’ll be the one hiring. Selling. Managing cash flow. Building culture. Losing sleep when payroll gets tight or a customer churns.

And when you get the deal right, you’ll be the one who earns the upside. Not the advisor. Not the lender. Not the guy in the Slack group who said he “wasn’t sure.”

The Bottom Line

“Is this a good deal?” is the wrong question.

Ask instead: “Does this deal make sense to me, based on what I know, what I’ve learned, and the risk I’m willing to take?”

If the answer is yes—then stop waiting for someone to say it’s okay. Step up. Sign the LOI. Close the deal.

Own it.