Simple but Brilliant: The Question that Won the Deal

I was recently at a buy/sell meeting—one of those rare opportunities where the buyer and seller meet in person to better understand the nuances of a business and get to know each other beyond the numbers.

As we toured the operation, the buyer asked thoughtful, highly specific questions about processes. It immediately demonstrated to the seller that this buyer genuinely wanted to understand how the business worked from the inside out. That may sound obvious, but you’d be surprised how many buyers rush through operations and focus almost exclusively on financials.

This seller was a fourth-generation owner, and sharing his story clearly mattered to him. The business wasn’t just an asset—it was a legacy.

After the tour, we gathered in a small conference room. The buyer thanked the seller and sincerely complimented him on what he had built. Then he asked a simple but powerful question:

“If you were 30 years younger, what would you do to grow the business?”

That one question changed the tone of the entire meeting.

It gave the seller space to reflect—to reminisce about ideas he wished he had pursued and lessons learned from things that didn’t work. For a moment, he got to revisit the “what ifs” of his career. It wasn’t an interrogation; it was a conversation rooted in respect.

After another hour discussing strengths and weaknesses—most of the buyer’s questions already answered—the buyer looked at the seller and said:

“It would be an honor to take over your legacy.”

It nearly brought the seller to tears.

This was a highly sought-after business, and the buyer faced stiff competition. But in that moment, he separated himself from the pack. The deal was essentially his to lose.

In competitive markets, buyers need to understand how to stand out—and notice that “standing out” doesn’t mean being aggressive or overly analytical. We saw other buyers fixate on sales trends and cost-cutting strategies. While financials are the lifeblood of any company, you have to read the room.

Sometimes, this isn’t the moment to drill into the numbers. For many sellers—especially long-term or family owners—the priority is finding someone who will carry on their legacy, not someone who highlights every imperfection in how the business was run.

A simple takeaway: write out your questions before the meeting. You may be surprised how many are answered just by walking the floor and listening. Focus your questions on operations and people—not just numbers. The financials will be thoroughly examined during due diligence.

Simple questions. Genuine curiosity. Real respect.

Sometimes, that’s all it takes.