When you’re buying a business, asking tough questions is part of the job. But that doesn’t mean it’s easy, especially when you’re trying to build rapport with the seller.
Push too hard and you risk souring the relationship. Stay too soft and you risk missing something critical. So how do you strike the right balance?
The truth is, asking difficult questions doesn’t have to feel confrontational. In fact, when done right, it can strengthen trust and move the deal forward. Here’s how to ask the hard stuff without tanking the deal.
Understand the Seller’s Mindset
Before you dive into tough questions, take a moment to step into the seller’s shoes.
For most small business owners, selling their business is deeply personal. It’s not just a financial transaction—it’s their identity, reputation, and legacy on the line. They’re handing over something they’ve built over decades.
That context matters. When a buyer starts firing off sharp questions without establishing trust, sellers can get defensive. And once trust is lost, it’s hard to recover.
So before you press for answers, make sure the relationship can support it.
Set the Tone Early
One of the best ways to avoid awkward conversations later is to set expectations early.
During your early calls or at the LOI stage, say something like:
“As we move forward, I’ll need to ask some pretty direct questions about the business—some of them might be sensitive. My goal isn’t to nitpick, it’s to make sure I fully understand what I’m stepping into. That way, we can get to the right outcome for both of us.”
This kind of framing disarms sellers. It shows you’re not trying to attack them—you’re doing your job.
Focus on Curiosity, Not Criticism
The difference between a good question and a deal-killing one often comes down to tone.
Instead of:
“Why is your employee turnover so high?”
Try:
“Can you walk me through your hiring and retention challenges over the last year?”
Instead of:
“Why are your financials such a mess?”
Try:
“It looks like the books were done in-house. Would you mind explaining the process and how consistent it’s been over time?”
This approach is more than just polite. It keeps the seller engaged and less defensive, which means you’ll get better, more honest answers.
Use Diligence as a Tool, Not a Weapon
It’s tempting to treat diligence as a game of “gotcha.”
But successful buyers use diligence to build clarity, not score points.
If your QofE team uncovers aggressive add-backs or working capital issues, don’t show up to the next call swinging.
Instead, bring data and stay calm:
“The report flagged a few recurring expenses that were added back as one-time costs. Could we walk through those together to better understand the rationale?”
This keeps the conversation grounded in the facts, not emotions.
Use Advisors Strategically
Sometimes, the tough questions carry more weight coming from a third party.
Your diligence provider, accountant, or attorney can raise sensitive points in a way that creates distance between you and the friction.
For example:
“Our CPA had a few questions around tax treatment and potential liabilities—do you mind if we loop them in to walk through the specifics?”
You’re not hiding behind your advisors, but you are using them as a buffer when the stakes are high.
Ask Questions Gradually, Not All at Once
Diligence is a process, not a pop quiz. Dumping 40 tough questions on a seller at once can feel overwhelming or hostile.
Instead, batch questions into smaller groups, prioritize the most important ones, and give the seller time to respond.
For example:
“Here are a few things we’re reviewing this week—can we aim to talk through these by Friday, and then move to the next set next week?”
This keeps momentum going without overwhelming the other side.
Acknowledge the Elephant in the Room
Sometimes the hardest questions are the most obvious ones:
- Why are revenues declining?
- What happens if your top customer leaves?
- Why aren’t you offering seller financing?
When you avoid these questions, it creates mistrust. The seller knows you’re thinking about them. They’re probably thinking about them too.
Instead, say:
“I imagine you’ve had a few conversations about this already, but I’d love to understand your perspective on [topic].”
It shows you’re willing to go there—respectfully.
Use Silence as a Strategy
Not every tough question needs to be a direct one. Sometimes, you can get more insight just by pausing.
If the seller offers a vague answer, don’t rush to fill the space. Let it sit.
Seller: “Yeah, we had some customer turnover last year, but that’s all sorted.”
You: *…
That pause often prompts the seller to elaborate. And those second answers are usually more revealing.
Be Honest About What You Don’t Understand
Trying to sound like an expert when you’re not is a fast way to miss something important.
If the seller throws out jargon or talks in generalities, don’t be afraid to slow things down:
“Sorry, I’m not sure I follow. Can you explain that one more time?”
Clarity beats ego every time.
Frame Questions Around Outcomes, Not Accusations
When you hit a sensitive topic, tie your question back to the goal:
“I want to make sure we’re both protected after closing, and part of that is understanding how these agreements work. Could we take a closer look at the vendor contract?”
This framing signals that you’re trying to solve something, not poke holes for the sake of it.
Know When to Push and When to Pause
Sometimes, a seller will bristle no matter how carefully you phrase the question. That’s okay. Take the cue.
You can always come back to the issue later, especially if you’ve already flagged it for follow-up.
What matters is staying calm, staying respectful, and keeping the long game in mind.
Final Thoughts
Asking tough questions is part of what makes you a serious buyer. But how you ask matters.
When you lead with curiosity, frame conversations with care, and stay focused on outcomes, even the hard conversations can move the deal forward instead of backward.
It’s not about being aggressive. It’s about being thorough, fair, and intentional.
Because in M&A, the buyers who close good deals aren’t the ones who avoid friction—they’re the ones who navigate it well.
Contact us today or book a free consultation and learn how we can be a trusted partner on your next deal!
