The CoS Costume Party is Frightening For All The Wrong Reasons

THE COUL & GOLD BRIEFING · ISSUE Nº 35 · October 13, 2026

Halloween is weeks away, and there are two more issues of the Briefing between now and then. But I've already started putting up my decorations, so I have costumes on the brain. (Early? Yes. Sorry? No.)

Lately the Chief of Staff conversations I'm in keep showing up in costume, and six of them scare the crap out of me. They scare me more than the house on the corner that hands out toothbrushes. Each one has an antidote on a shelf in the Vault. (Yes, I'm selling something. It's October. Everyone's selling something, mostly fun-size Snickers. But my product will give you decidedly fewer cavities.)

Grab a pillowcase. We're going door to door.

Slap "Chief of Staff" on any job and it sprouts a horn. The EA who deserved a raise the budget couldn't cover. The program manager the CEO likes. The consultant who never left. The founder's college roommate, who is "great with people."

Dwight Schrute was Assistant to the Regional Manager, a title that meant whatever Dwight needed it to mean that afternoon. That's the Unicorn. Everybody wants one and nobody knows what it is, so everyone dumps the problem they've ignored since 2023 at its sparkly little hooves. The board wants a strategy. Sales wants a forecast somebody believes. The CEO wants the weekly leadership meeting to stop running long. Surely the magical horse can do all of it by Thursday.

Meanwhile most executives read a Chief of Staff job description the way they read terms of service. Scroll to the bottom, click yes, and never look at it again until something breaks.

From the Vault: Fill out The CoS Role Scorecard (Shelf 01) with your executive in the room. Alone at your desk, it's a wish list. If the meeting keeps sliding off the calendar, say it out loud: "I need your full attention for this one, because it’s fundamental to how I do my job and how effective I am for you." If the role doesn't exist yet, The Mandate Architect builds it before anyone orders business cards. And if you're hiring, The CoS Interview Loop Kit keeps every interviewer asking about the job, so nobody falls in love with the horn.

Carson ran Downton Abbey for six seasons and two movies and never once sat down to dinner with the Crawleys. Lovely man. Wrong job.

This costume turns a member of the executive team into staff. You take notes in the leadership meeting instead of taking part in it. You book the offsite and learn the agenda along with everyone else. You find out about the reorg at the all-hands, next to the interns, and pretend you knew.

A Chief of Staff sits on the executive leadership team. If you're not on it, you're in a tux passing canapés. Here's a quick test: do you have a standing one-on-one with every member of the leadership team? Those meetings are how you see the organization for all that it is. Without them, you're just polishing the silver.

It's also why Suzi and I insist this is a senior leadership job. Relationship building and being likable are two different skills, and the Butler only gets paid for the second one.

From the Vault: Shelf 08, The Executive's Side, talks to your executive directly. Start with The Executive's Side, Signed, which puts their commitments in writing. Then use The EA and Chief of Staff Division of Labor (Shelf 01) to send the canapés to someone whose job it is. If the butler work is real, hire for it. An executive assistant who reports to you, with a dotted line to the executive, takes coordination off two plates and trims the executive's list of direct reports while you're at it.

"I can do my own travel. It'll take two minutes."

The McCallisters handled their own travel too. They left a child home alone in Chicago.

Founders say this, typically, brimming with pride because founders believe they can do it all. (And they’re so low-maintenance! Doesn’t that make them the greatest founders ever? Uh… no it does not.) Two minutes turns into forty in the airline app, then a rebooking from the gate, then a call from the hotel about a reservation that doesn't exist. And even if it really takes two minutes, that's two minutes the CEO isn't thinking about the product. They're thinking about their aisle seat on a freaking airplane.

Some executives also think needing help makes them high maintenance. Really? Because thinking you’re low-maintenance actually makes you high-maintenance. Someone in the org is absorbing the work that invariably pops up. Meanwhile, you still think you can schedule yourself in 60 seconds flat which means you basically never say “no” to anyone. That sounds remarkably efficient.

The scary part is what it reveals — an executive who thinks their own time is free. That executive will price your time the same way.

From the Vault: The Executive Time Portfolio Audit (Shelf 03) shows the executive where the hours went, straight from their own calendar. Run it on an ordinary week. Executives wave off a terrible week as a fluke. They have no defense for an ordinary one. Then pair it with The Gatekeeping Rules (Shelf 09), so the question of what reaches the executive becomes a standing rule instead of a fresh negotiation every Monday.

"You're here to learn the business, so you can take over a vertical."

Cousin Greg showed up at Waystar Royco to learn the business. Four seasons later, he'd mastered the document shredder and very little else.

In daylight it's a Chief of Staff. Under the full moon it sprouts fangs and a VP of Sales title. The whole point of this job is a senior executive who sees the entire organization and owns no vertical. The chief is the one person playing political chess seven moves ahead, spotting trouble from a country mile that nobody else can see. Very few people can do that, and this costume treats it like an internship.

Promise the chief a vertical and they spend a year auditioning for it. Every decision bends toward the exit, and nobody bothers to invest in the mandate. The role pays out over eighteen months, and you find yourself interviewing with a(nother) vampire at Month Eleven.

Plenty of chiefs move into operating roles later, and that can be a terrific outcome. Plan it in the open. Just don't hire someone, call the job Chief of Staff, and treat it like a stepping stone during the entire eighteen-month stint.

From the Vault: Track your Scorecard all year, so when raises come up you have a better pitch than "I averted a bunch of crises." Try "You wanted these things. Here's how I delivered each one." Then bring The Compensation & Title Brief (Shelf 10) to your executive before they bring up the vertical. Growth, no change of species required. If someone really is leaving, The Transition Runbook keeps the exit clean, and the Interview Loop Kit makes sure the next hire isn't another vampire wanting to suck your blood.

"I'll make the announcement soon. Just go meet people, and we'll figure it out as we go."

Ned Stark rode into King's Landing with a big title and nobody backing it. You remember what happened to his head.

With no announcement, every coffee starts with you explaining why you exist. Engineering gives you the summer-intern tour. Finance decides you're an auditor and goes dark. The head of sales asks if you're "the new EA," and you laugh like it's a joke, because it had better be. By the time the announcement goes out, if it ever does, the building has already decided who you are.

Chiefs of Staff love to say they have influence without authority. What a crock. Suzi wrote about this in the Briefing, and a light bulb went off for me. Influence runs on authority. If nobody can see the signals of yours, you have nothing to stand on, and the announcement is the first signal anyone sees.

From the Vault: The Comms Cascade Planner (Shelf 04) sequences who hears about you and when, so your peers don't learn about you from the company newsletter. Draft the announcement yourself and hand it over with the cascade attached. "Soon" becomes "today" when the only step left is pressing send. While you have their attention, ask the question I ask every new executive, "How should I disagree with you? Because I'm going to so let’s figure out a way to do it without making you livid." And when the coffees finally start, spend the first five minutes of each one on anything but work. That's the part people will remember when they’re stuck in a hard conversation with you.

"You're at the intersection of all the cross-functional work, so rolling out AI is your responsibility."

Picture a scarecrow at a crossroads, arms out, pointing at every direction simultaneously. That's the pitch. You see across every function, so every orphaned initiative finds its way to you, and right now AI is the biggest orphan in the building. Someone has to pick the tools, write the policy, train the teams and answer to the security review. Somehow that someone is you, on top of everything else.

Everyone's so busy asking whether the company can roll out AI that nobody has asked who owns it after launch. Ian Malcolm would have notes. And the software is the easy part. Every person in the building brings their own fears and baggage to AI, while a fresh crop of startups tries to sell your executive an "AI Chief of Staff," which tells you how well the market understands the job.

Your job is to be an omniscient narrator: step back, see the whole picture, ask what's actually going on. Own the rollout forever and the narrator becomes a character, buried in license counts and training calendars.

From the Vault: The Incubation Charter (Shelf 09) lets you launch it and leave, with the permanent owner and the handoff date in writing before anyone buys a single license. The Mandate Drift Log (Shelf 10) records everything that lands on your plate, so when someone asks why the strategy work slipped, you have receipts.

The Full-Time Vault has ten shelves and 44 documents, workbooks and interactive tools. Please don't read it front to back. Nobody reads the whole bag of candy in one sitting either. (Fine. Some of us do. But we pay the price for it later.)

Wear whatever you like to the office party on October 31st. Just take it off before Monday's leadership meeting. And if nobody invited you to Monday's leadership meeting, then reply to this email immediately. We have a lot of work to do before Thanksgiving…

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