How to Evaluate a Buyer’s Track Record - Especially When Things Go Sideways

Most buyers are easy to like when the business is doing well.

But the reality is every business hits rough patches.

One of the questions you need to ask is “Who is this person when times get tough?”

As an operator, I’ve learned that what matters most is how someone shows up when things aren’t easy. That’s when leadership, empathy, and judgment reveal themselves.

The Deeper Questions That Really Matter

If I were selling my company today, I’d want to get a better understanding of the person behind the offer.

Not just their experience, but how they think, what drives them, and how they treat people under pressure. I’d ask:

• What experiences shaped how you lead today?

• When things went wrong, what did you do and what would you do differently?

• What was in your control, and what wasn’t?

• How did you help your team through those times?
  

You learn a lot from how someone talks about their toughest moments.

Do they take ownership? Reflect? Improve?

References Are More Than a Checkbox

Reference checks are essential, not just to catch red flags, but to understand how to get the best out of someone.

A reference can give you insight into someone’s strengths, their blind spots, and how they’ve grown through challenges.

I’d even suggest asking a spouse, friend, or trusted partner to meet the buyer. They’ll often notice communication dynamics or emotional tone you might miss.

Understand how the buyer makes money

If it’s through aggressive growth, financial engineering, or juggling a portfolio, think carefully. The way a buyer makes money shapes the decisions they’ll make post-sale.

One Thing Founders Should Never Overlook

If you’re evaluating a buyer, don’t just look at the LOI.

Ask about:

• Their temperament in crisis

• How they connect with people from the boardroom to the front line

• Whether they’ve worked through failure

• If they understand how their own leadership shows up

• How are decisions made?

  • Is it just them? A board? A committee?

    • This will tell you a lot about how quickly things move, who actually has control, and whether your team will be empowered or sidelined.

      
      

And if you’re unsure, involve someone you trust in the process. Sometimes an outside perspective reveals what you’re too close to see.

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