Your Chief of Staff Has a Leo McGarry Problem

THE COUL & GOLD BRIEFING · ISSUE Nº 28 · SEPTEMBER 1, 2026

Somewhere this week, a Chief of Staff who can run a board meeting in her (or his!) sleep stood frozen in an aisle at Target, holding two functionally identical binders, trying to figure out which one the syllabus meant.

I see you. I'm you.

The academic calendar has begun its annual campaign of terror, and it doesn't care that the board deck is due Thurs. So before we get into any of this: if the last week has felt like a lot, that's because it is a lot. Back to school is a second job that arrives with no onboarding, no budget, and a supply list written by someone who clearly hates you. And for those of you who are childless and not experiencing the onslaught of dread that this week brings, bless you. Because you’re carrying the slack that parents can’t hold even though work still need to get done. Everyone reading this is carrying more than they're letting on. Consider this your permission to have a deeply mediocre week and file it under “A Win.”

Now. On to the man who ruined this job for the rest of us.

There's a gap between what people think this job is and what it actually is. It's enormous. And it's steadily wrecking organizations that hire for the fantasy version of the role and then act surprised when the fantasy doesn't show up for work.

The fantasy is intoxicating, and I understand the appeal. Direct access to the CEO. A bird's-eye view of the entire organization. Real influence over how the place runs, and a seat at every table worth sitting at. On paper it's the best job in the building. I've done it, and the good version is genuinely thrilling.

But nobody puts the cost in the job description, so the people who chase the title without understanding the toll get a rude education, usually somewhere around month four.

If you're doing this right, you sit between everyone and belong to no one. The CEO sees you as the person who handles problems. The C-suite sees you as someone with the CEO's ear, which means they're cultivating you and being careful around you, often in the same conversation. The staff sees you as management. And you absorb all of it, all day, carrying things you can't repeat, making calls nobody will ever credit you for, and serving as the organizational pressure valve for stress that has nowhere else to go.

It's a lot. It's also a pretty typical Tuesday.

People hear the title and picture a corner office. The reality is closer to triage nurse. You field complaints from every direction and decide, in real time and usually in a hallway, what rises to the level of "Houston, we have a problem" and what you handle on your own, with no fanfare and no evidence it ever happened.

And the role can be extraordinary. I've watched Chiefs of Staff reshape how entire organizations operate, and when the seat is positioned correctly and the person in it was wired for the weight, the impact is remarkable. But that impact is invisible almost by design, because the chaos you prevent doesn't announce itself. You only notice it when it stops being prevented.

So where does the glamour myth come from? Partly the mystique of the White House, which keeps its grip on the imagination regardless of who's occupying it. Since I worked there for the Chief of Staff, I can tell you it's an extraordinary place full of the savviest minds you'll ever meet, all pushing an agenda they believe in down to the marrow in their bones.

And partly it comes from Aaron Sorkin, who has done more to shape the public understanding of this role than any management theorist, business school curriculum, or actual Chief of Staff who ever lived.

Which is a mixed legacy at best.

The West Wing is one of the great television shows ever made. I say that as someone who's seen every episode and has opinions about all of them, including the ones nobody has asked me about. I met Martin Sheen in the West Portico — in real life. And I was Margaret, except that Margaret counted the calories in the White House Mess muffins and I very much did not.

Leo McGarry is brilliant, loyal, formidable, and beautifully written. He's also personally responsible for roughly half the misconceptions that make this role so consistently misunderstood by the people doing the hiring. Sorry, Leo.

Because the problem with Leo as a template isn't the drama or the mythology. It's the friendship.

Leo was President Bartlet's oldest and dearest friend. That relationship was the emotional spine of the show. The loyalty was unconditional, the trust came pre-installed, and they had decades of history before either of them walked into the building.

Corporate America watched this and drew precisely the wrong conclusion.

Aaron Sorkin’s view was find someone who knows you, trusts you, and has been in your corner since the beginning, and make them your Chief of Staff. It'll be like Leo and Jed. Deep trust. Real loyalty. Beautiful.

I need you to meet Mack McLarty.

Thomas "Mack" McLarty served as Bill Clinton's Chief of Staff from 1993 to 1994, and he was also Clinton's childhood best friend. They had known each other since kindergarten. By every account the friendship was genuine, warm, and deeply meaningful to both of them.

His tenure is widely regarded as one of the least effective in modern history, and not because he lacked intelligence, capability, or devotion. He had all three in abundance. But the Chief of Staff job doesn't reward friendship. It rewards political navigation, organizational orchestration, and the studied neutrality required to hold the trust of every constituency at once, and every one of those sits in direct tension with being someone's best friend.

When you're the principal's closest friend, you can't fully be the honest broker. You can't walk in with the hard news, because you care too much about the relationship to deliver it cleanly. And you can't hold the neutrality the job requires, because everyone in the building already knows whose side you're on.

The Chief of Staff is not your best friend. The Chief of Staff is the person who tells your best friend what they don't want to hear, on your behalf, when you can't, in the room when you're not there, and well enough that the person on the other end still feels respected.

That's a wildly different job description than "the person who loves you and has your back."

Leo worked on television because Sorkin needed someone Bartlet trusted completely, and a childhood friendship is the most efficient way to establish unconditional trust before the first commercial break. But in real organizations, unconditional trust is a liability. You want a Chief of Staff whose loyalty runs to the mission rather than to you personally, because the moment it becomes personal, the hard conversations stop happening.

And the hard conversations are the entire point.

In fairness, let me acknowledge what the show modeled correctly, because it got the big thing right.

Leo ran the building. He didn't do the President's job and he didn't do anyone else's job. He coordinated every function, sat in every room that mattered, and was the person through whom information flowed and decisions got made. His authority was unambiguous and universally understood, and nobody in that West Wing ever tried to route around Leo McGarry.

That's the model. One person, unambiguous authority, organizational integration at the highest level.

Corporate America took that model and did something genuinely impressive with it, which was to hollow it into nothing. It kept the title and stripped out the authority, the structural positioning, and in many cases the budget for a single dedicated human being. Then it wondered why it wasn't getting Leo McGarry results.

So here's what that infrastructure actually is, and why nobody films it.

Leo's authority didn't live in his personality. It lived in the machinery. The pre-read that landed before the meeting instead of during it. The decision log that stopped everyone relitigating Tuesday on Thursday. The cascade that got one message to eleven teams instead of eleven messages to eleven teams.

That's the entire apparatus, and it is, in the end, a stack of documents. Which is, I'm aware, the least cinematic sentence I've ever written.

It's also the whole difference between a Chief of Staff who runs the building and one who merely attends meetings inside it.

So Suzi and I spent the summer writing that stack down. All of it. Every artifact this job actually demands, at the depth you need in month two and the depth you need in year three, because those aren't the same document, and pretending otherwise is why most templates are useless.

And then there's the invisibility problem from earlier. The one where the chaos you prevent never announces itself, and then someone in a budget meeting asks, with genuine curiosity, what it is you do here. We built something for that, too.

That's most of what this fall is, honestly. We spent the summer rebuilding, sharpening, and in one case cheerfully setting fire to what we had, and the early reads have come back better than we had any right to expect. More on all of it shortly. And I do mean shortly.

The Chiefs of Staff who take this role chasing the mystique are the ones most blindsided by what it requires, because the access is real, the influence is real, and the weight that arrives with both is also real and significantly less photogenic.

You become the omniscient narrator. You know what everyone is thinking, what every faction wants, and what's forming under the surface long before it becomes a problem anyone else can see. You carry the CEO's confidences, the staff's frustrations, the C-suite's interpersonal weather, and whatever organizational anxiety has nowhere else to go.

None of that was in the Sorkin version. None of it appears in the job description. And none of it is glamorous.

What it is, when the role is working and the person in the seat was built for the weight, is meaningful in a way very few professional experiences ever manage.

But meaningful and glamorous are not the same thing.

The best Chiefs of Staff I know didn't take this job because it looked impressive. They took it because they were wired to belong to everyone and no one, to carry what others can't, and to make things work in ways nobody will ever fully see or credit.

That's the job.

Admittedly, Aaron Sorkin's version is better television.

Now go find the binder. The half-inch one.

— Rachael

If you read all of that while running a quiet audit on yourself, good. That's the correct instinct, and it's most of the reason we built the Chief of Staff Readiness Assessment.

Want an inkling? The free diagnostic takes five minutes. It won't tell you everything. It will tell you something. Take the free 5-minute diagnostic.

Want to understand your wiring? The Entry Assessment is $799 and about ninety minutes. Written and quick-judgment scenarios across twelve areas, built around the four that decide everything: your relationship with authority, your self-regulation under pressure, your judgment about information, and whether you can operate without a mandate. Every submission is read and every report edited by a practitioner, back to you within five working days.

Want to know exactly where to get stronger? The Full Assessment is $2,500. It's everything in Entry, plus a read of your professional profile, a sixty to ninety minute interview with a practitioner, a second independent analysis of that interview, and a shareable readiness profile you can put in front of an employer.

Your last three interviewers had opinions about your readiness. This has data.

One voice from inside the role. One from the blueprints. Same mission.