Why the Right Questions Matter More Than You Think
When it comes to buying a business, most people are so focused on cash flow, asking price, and due diligence checklists that they forget to ask the deeper, more revealing questions—the ones that can make or break a deal.
As a mentor, I’ve seen buyers do months of work only to be blindsided because they missed something crucial. In this post, I’ll walk you through three killer questions that buyers often forget to ask—but absolutely should. And I’ll show you why each one matters more than you realize.
“What Does a Typical Day Look Like for the Owner?”
At first glance, this question sounds casual. But don’t underestimate it—it’s a diagnostic tool.
The seller’s answer reveals operational complexity, staffing issues, owner dependency, and hidden risks. If the owner is working 80 hours a week wearing 10 hats, that’s a red flag. You don’t want to buy a business and inherit burnout.
Why This Question Is Often Missed
Buyers are usually so focused on the P&L that they forget to ask about lifestyle. But lifestyle is strategy. If the current owner is still in the trenches, it tells you that systems might be weak or the team isn’t empowered.
When you ask about the owner’s day, you’re really asking, “Is this business built to run, or built to drain me?”
“What Would You Do Next If You Were Staying?”
This is one of my personal favorites. It’s disarming and insightful.
Why? Because it opens the door to the seller’s vision. You find out what opportunities they see but haven’t yet capitalized on. Sometimes, it reveals that the business has been coasting. Other times, you’ll uncover growth gems hidden in plain sight.
What the Answer Tells You
You’re listening for one of two things: strategic clarity or hesitation. A seller with clear ideas probably left growth on the table—which is your upside. A seller with no answer? That might mean the business has hit a ceiling.
This question also gauges whether the seller’s exiting on a high or running from a dead-end.
“Why Hasn’t Someone Else Bought This Yet?”
This is the toughest question—but the most important one. It takes guts to ask it, and even more confidence to interpret the answer.
The seller’s reaction is as telling as the words themselves. Do they get defensive? Do they give a clear, honest reason? Are there objections that keep coming up from other buyers?
The Psychology Behind This Question
Sellers often avoid disclosing lingering issues. But when you ask why no one else has pulled the trigger, it forces them to get honest.
Maybe the price is too high. Maybe it’s a great business with poor marketing. Or maybe there’s something serious under the hood. Whatever the reason, you deserve to know.
Bonus Questions to Ask Before You Close
While these three are my top game-changers, here are a few honorable mentions:
- “What skills or licenses do I need to run this business effectively?”
- “What would you do differently if you had to start again?”
- “Who are your top 3 competitors, and why do customers choose you instead?”
These follow-ups round out your perspective and help reveal blind spots before it’s too late.
How These Questions Help You Avoid Regret
Buying a business isn’t just a financial investment—it’s a lifestyle shift. These questions cut through the surface and reveal what you’re really signing up for.
They also give you leverage. When you ask smart, unexpected questions, you gain respect—and often, better deal terms.
Final Thoughts from a Mentor Who’s Seen It All
Look, no question alone guarantees success. But asking the right questions sets you apart from the amateurs. It’s what separates the buyers who thrive from those who just survive.
If you’re preparing for your first acquisition or want a second set of eyes before you commit, I’m here. Let’s build your strategy—and your question list—the smart way.