When Bad Advice Hurts Everyone Involved

Welcome back to the Mid Market Insider!

Today, we’re discussing a deal I was recently a part of where “bad advice” played a huge role, and how to discern between good and bad advice for your business.

Before we dive in…

When Bad Advice Hurts Everyone Involved

Bad advice isn’t always a zero-sum game.

Sometimes, it doesn’t just hurt one side of a deal… it hurts everyone.

Here’s a real example from a deal I worked on recently:

The sellers were firm about doing things in a very specific order.

Task A had to be completed before moving to Task B.

Nothing overlapped. Nothing ran in parallel.

Their attorney didn’t object to this approach, so everyone went along with it.

On paper, it sounded reasonable.

In practice, it nearly killed the deal.

What Went Wrong

Two things mattered more than anyone wanted to admit:

1. Competing priorities

The seller’s attorney was juggling multiple transactions at once. Our deal wasn’t his top priority, it was third or fourth on the list. Because everything had to happen sequentially, every delay compounded the next step.

2. A ticking clock

The bank’s approval had a deadline. As delays piled up, we came dangerously close to missing it altogether, not because of deal issues, but because of pace.

This had nothing to do with price.

Nothing to do with structure.

Nothing to do with reps, warranties, or legal complexity.

It was purely about process and timing.

A Delicate Point

I’m always cautious telling business owners to second-guess their attorney or M&A advisor. I know how biased I can sound as a buyer.

After all, I benefit from deals closing.

But here’s the reality most sellers don’t want to hear:

If this deal died, I would move on to the next opportunity.

The sellers would have to start over with a new buyer, a new process, and a lot of lost momentum.

Getting the deal done mattered far more to them than it did to me.

Time Really Does Kill Deals

People roll their eyes at the phrase “time kills deals.”

I get it… it sounds cliché.

But in the deal world, it’s absolutely true.

In this case, the process dragged on for more than 12 months.

With a different approach, we could have closed in closer to three.

To make matters worse, during that extended timeline, the seller had a personal emergency unrelated to the business. Completely understandable, but it slowed things down even further.

Had we moved faster earlier, the deal would have been done long before that happened.

The Lesson

Selling a business isn’t just about valuation or legal terms.

It’s about momentum.

The order of operations matters.

The pace matters.

And bad advice, even when well-intentioned, can quietly derail a deal that otherwise should have closed.

If you’re ever in a sale process, don’t just ask what needs to get done.

Ask how and when it should happen, and whether the process you’re following actually serves the goal of getting the deal closed.

Because once momentum is gone, it’s very hard to get back.

That’s all for today’s newsletter! Thanks for reading!

📅 Next Week:

Next week, I’ll be discussing one of the biggest mistakes bosses make when delegating, and how you can set your team up for success instead of frustration.

Keep building,
Nick