What to Do When Things Go Sideways in Diligence

You made it past the LOI.

You’re in exclusivity.

You’re deep in diligence.

And suddenly…

📉 The buyer “finds something”

📑 They want a $2M escrow

🔁 The timeline shifts

📝 A surprise clause shows up in the purchase agreement

Welcome to the part of the deal where leverage disappears and emotions run high.

Why Diligence Gets Messy

By this point, buyers have spent real money:

• Legal teams

• Financial advisors

• Background checks

• Site visits

They’re invested. But they’re also nervous.

So they push to de-risk the deal:

• Escrows

• Holdbacks

• Indemnities

• Working capital adjustments

• Reps and warranties insurance

Some of this is fair.

Some of it’s gamesmanship.

Your job? Stay calm. Stay structured.

3 Rules for Handling Last-Minute Changes

1. Don’t React Emotionally

The instinct is to get angry. To walk. To say, “Screw this, they’re playing games.”

Resist it.

Instead, slow things down. Create space.

2. Don’t Immediately Counter

Let the silence do the work.

If they say, “We need a $2M holdback,” try:

Then… wait.

You’d be surprised how often that $2M turns into $1M, or disappears entirely.

3. Propose Thoughtful Alternatives

If you’re going to counter, do it with logic.

• Escrow too large? Suggest rep & warranty insurance.

• Worried about a customer churn? Offer a short-term earnout.

• Timeline too long? Add a drop-dead date.

Make it easy for them to say yes without losing face.

The Power of “Acceptance Time”

One of the most underrated negotiation tactics?

Let time work for you.

Sometimes, the best move is no move.

Let the buyer sweat. Let internal pressure build on their end.

Silence isn’t weakness. It’s strategy.

Deals Get Won in the Last 10%

Everyone’s exhausted. Emotions are high. The finish line is close.

And this is exactly when mistakes happen.

So slow down.

Stay rational.

Let the buyer show their cards.

And remember: