The $400,000 Body Double and Defining the Chief of Staff Role

THE COUL & GOLD BRIEFING · ISSUE Nº 23 · JULY 28, 2026

There is a First Round Review essay from 2017 called, "Why You Need Two Chiefs in the Executive Office," and if you have spent ten minutes in the Chief of Staff world you have had it sent to you, usually by someone who means well. Influitive's CEO Mark Organ explains how a Chief of Staff turned him from a founder forgetting his third meeting in a row into something the piece cheerfully calls "superhuman." Nine years later it is still the canonical venture take on the role, which is a problem, because it is mostly wrong.

I want to be fair, though, because one part of it is the best advice on this subject I have read anywhere, no wink at all. So let's start where he's right in his thinking.

Organ puts his Chief of Staff in the same room. All day every day for an entire month. They listen to his musings, sit in on his calls and his one-on-ones, and read his email. He Slacks them twenty times a day and, in his words, holds nothing back. The stated goal is that the Chief of Staff can eventually predict how he would decide. And before anyone is hired, he simulates the job with a real project and watches how the candidate thinks under pressure.

This, kids, is the whole ballgame. Judgment does not transfer through a job description or a jam-packed two-day handoff that appears to be thorough but doesn't even scratch the surface; it transfers through proximity, repetition, and a executive willing to think out loud in front of someone allowed to disagree. Most executives will not do this. They want the output without the exposure, the board deck without anyone watching them flail toward it. If you take one thing from his essay, take this: your Chief of Staff cannot represent your thinking if you have never let them watch you think.

Here is the ultimate irony, though – the onboarding he describes builds an organizational mind, while the role he builds around it is a body double. His practice, in short, is smarter than his theory, a problem I intend to hold against him for the next thousand words.