Who should negotiate a high-stakes deal for your company?

The person who should negotiate a high-stakes deal is someone whose name is not on the outcome. When the deal is personal, that is rarely the CEO alone.

I learned this most clearly from Matthias Schranner, one of my guests on the DEALMACHER podcast. He spent 17 years with the police, six of them undercover. Then he worked as a hostage negotiator trained by the FBI, the US Federal Bureau of Investigation. Today he advises corporations, governments and the United Nations in more than 40 countries. Forbes has called him one of the best negotiators in the world.

He is the best negotiator I have had on the show. And the first thing he told me was that he does not negotiate the deals that matter to him personally. Inside his own company, he has one rule that he calls “law, almost religion”: he never negotiates his own prices. Someone else does. I wrote about it in my CEO Briefing on why you should never negotiate your own high-stakes deals.

Why should a CEO not negotiate their own deals?

Closeness to the deal makes you emotional, and emotions lead to mistakes. Schranner says it directly: “The closer I am to the object of the negotiation, the more emotional I get – and the more mistakes I make.”

He has a simple test for it. Any of us could negotiate a colleague's salary calmly and in a structured way. Now imagine negotiating your own. Suddenly the conversation is about more than the number. It is about recognition, fairness and being seen. The moment the deal becomes about you, you stop playing well.

Distance keeps your judgment intact when the stakes are personal.

Why does the person with the most at stake often negotiate worse?

The person with the most at stake often negotiates worse because their emotions show at the table. Many operators assume this person should sit in the chair. They care the most and they know the most. Both are true. In Schranner's experience, the same person is exactly the one whose emotions will leak into the room. Caring more makes you worse at the table.

This shows up wherever the stakes are high and the object is personal:

• The exit: the founder selling the company they built.
• The partnership: the CEO renegotiating a partnership they championed.
• The identity deal: any deal where your identity is quietly tied to the outcome.

In each case, the instinct is to lead the conversation yourself. And in each case, that instinct is the risk.

How much does the person at the table change the result?

The person at the table can change the result by a wide margin, even when the facts are identical. I saw this in 2017. At Microsoft ScaleUp, I organised a negotiation workshop for top VCs, venture capital investors. We invited an internationally renowned negotiation coach. For many years, he had been part of negotiations between Israel, Palestine, the US and many more.

In a role-play, the VCs worked in pairs. One played a founder who wanted to sell a startup. The other played a corporate M&A manager, responsible for mergers and acquisitions, who wanted to buy it. All pairs had identical information, such as the startup's revenues and the criteria that mattered to the buyer.

The outcomes were very different:

• Some pairs did not close a deal at all.
• Some agreed on a 10 million dollar exit.
• Some “founders” sold their startup for more than 500 million dollars.

The difference came from how each founder communicated, negotiated and shaped the perception of value. I described the experiment in my CEO Briefing Perception trumps reality. If the person at the table can move a result that far, choosing that person is a leadership decision.

Can the CEO stay in the room during the negotiation?

Yes, the CEO can stay in the room, as long as they are not alone in it. Schranner's point is a split of roles. The person carrying the emotional weight and the person carrying the negotiation should be two different people.

So you bring someone whose name is not on the outcome. That person needs three abilities:

1. Saying the hard number: they state the price out loud.
2. Sitting through the silence: they wait after the number and let the other side answer.
3. Staying calm under pressure: they do not give in when the other side pushes.

The silence is part of the job. In my CEO Briefing on demands versus arguments, Schranner describes what many people do after they present their number. They explain, they soften, they fill the silence. In his words: “And then they keep talking – and they destroy everything they just built.”

What if there is no one else who can negotiate for you?

If there is no one else, you build that person before you need them. Schranner's warning is clear: without someone else, your own vanity becomes the most expensive person in the room.

The work is to build people around you who can negotiate on your behalf, ahead of the deal. Convincing yourself that you will be the exception under pressure is the riskier plan.

Schranner sees negotiation as a game with patterns. You play it better from a small, deliberate distance. The professionals he trains are the calmest people in the room. Often they care visibly less in the moment, because they have removed themselves from the part of the deal that would make them careless.

How do you decide who should negotiate your next deal?

Ask one question before you walk in: am I the right person to say these numbers out loud, or just the most attached? Then check the deal against three points:

1. Closeness: is my identity tied to the outcome, as with selling my own company or a partnership I championed?
2. People: who around me can say the hard number and sit through the silence?
3. Roles: if I stay in the room, who carries the negotiation, and what is my part?

The hardest deals of your career will be the ones you are closest to. That is precisely why they are the ones you should not be running alone.