Find Something to Complain About

A note to young leaders.

On the art of the deal – from the late John Caldon.

In 1998, I was sitting in John’s office at Macquarie Group when an Executive Director walked in to brief him on an infrastructure deal, eighteen months in the making.

Signing was days away but everyone on both sides was getting nervous. Doubts that were tolerable in month nine have a habit of becoming existential in month eighteen.

“Find something to complain about,” John said. “Pick a clause and tell them the wording has to change or the deal could fall over.”

There is a strange moment near the end of any large transaction when reason has done almost all it can. The numbers have been checked, the documents drafted and the commercial terms settled. There’s nothing left to do but sign.

But before the signing comes the lull. Many deals lie down in the lull and never get back up.

John turned to me and continued:

“Everyone gets cold feet before signing a big deal, Adam. The person complaining sets the agenda. You wanna be the person doing the complaining.

Give them a small problem to solve, or they’ll invent a big one for you. And if they refuse your request, even better. Reluctantly concede at the last minute and they get to feel they won.”

A manufactured grievance, held with conviction and surrendered graciously at the eleventh hour, keeps the other side responding rather than reflecting. Reflection is where deals go to die.

At the end of a big deal, there are only two roles on offer. Be the squeak – or spend the last week frantically looking for the grease.