They Were Playing a Different Game

Every owner I know who has sold a business says something similar once it’s over.

They don’t talk about the multiple.

They don’t talk about the closing dinner.

They say,

“Their A-team was playing a different game than mine.”

Not smarter people.

Not better people.

Just a different game.

The buyers had been there before. Many times. They knew how the questions would land. They knew where things would tighten. They knew which moments mattered and which ones didn’t.

From the outside, it can look like talent. Like confidence. Like brilliance.

It usually isn’t.

What looks like god-given ability is often just positioning. Experience stacked on experience. Familiarity with a process that only shows itself when the stakes are real.

Buyers don’t improvise. They run a process.

A calm one. A practiced one.

Across the table, the business owner is often doing something very different. Reacting in real time. Reading the room. Managing confidence as new questions surface and old assumptions get tested.

It isn’t incompetence.

It’s asymmetry.

One side is operating from a playbook.

The other is drawing from an emotional account that’s never been tested this way before.

• Every surprise takes a withdrawal.

• Every delay costs a little confidence.

• Every unanswered question leaves a mark.

None of it feels dramatic in the moment.

But it accumulates.

By the time diligence is underway, the tone has already shifted. Decisions that once felt routine now feel exposed. Gaps that never mattered before start to matter. Not because the business is broken, but because pressure changes what’s visible.

That’s usually when the realization lands.

“If I had known this earlier, I would have prepared differently.”

That realization doesn’t come from the numbers.

It comes from how the business behaves once scrutiny arrives.

Diligence doesn’t create that behavior.

It only reveals it.

By then, the game is already in motion. And whatever is uncovered, strength or fragility, is priced in long before anyone talks about fixing it.

That moment has a name.

If this feels uncomfortably familiar, it usually means the risk hasn’t shown up yet, but it will.