You Slapped a Sticker on It and Called It a Chief of Staff

Here is a real job posting I did not write, could not have improved on for comedic purposes, and will now perform an autopsy on out of professional obligation.

“Chief of Staff. Must thrive in ambiguity. Wear many hats. Be a strategic thought partner and force multiplier for our visionary CEO. Own the cadence. Drive alignment. Be the connective tissue.”

Every phrase in that posting is doing the same job, and the job is hiding. “Thrives in ambiguity” is not a requirement. It is a confession, made in public, that nobody sat down and decided what this person is actually for. “Connective tissue” is what you reach for when you want the gravity of an org chart without the inconvenience of putting anyone on it. (And if you’re going to analogize the Chief of Staff role to biology, could we please acknowledge that it’s a major organ and without it would involve death? Because that’s what it’s supposed to be.) And “wear many hats” is the tell that would get a person convicted in an actual courtroom, because it means, “We have four jobs, none of them senior enough to justify a real hire, and we are going to staple them to one title and call the staple a strategy.”

I have watched this happen to smart people for twenty years. A founder wakes up drowning and instead of asking what, specifically, is drowning them, they post a job. They do not design a role. They post a feeling. And because “Chief of Staff” is the one title in the modern org chart that costs nothing to hand out (no budget line, no headcount fight, no call to the board), it becomes the sticker you put on any job you haven’t thought through. Executive assistant, paste the sticker on. Ops manager doing three jobs, paste the sticker on. Twenty-six-year-old MBA who reminds you of you at that age, paste the sticker on and watch them believe it.

So let’s build one properly, out loud, so you can see the difference between a sticker and a role.

“Thrives in ambiguity” is not a requirement. It is a confession admitting that nobody decided what this person is actually for.

Meet the Founder Who Almost Did This to Herself

Call her Dana. Dana runs Meridian, a health-tech company that went from forty people to a hundred and eighty in eighteen months, which sounds like a victory lap until you notice what it actually means: somewhere in that growth, Dana became the only place in the company where product, commercial, and clinical operations still talk to each other.

Each of those three functions is, individually, run by a competent adult making sound decisions. They just make sound decisions that collide the moment they hit the executive level, because nobody below Dana has the standing to catch the collision before it reaches her desk. So Dana’s week is not spent leading. It is spent reconciling. She is the human equivalent of a cross-functional sync that never ends, and she is starting to suspect that if she disappeared for a month, the company would not notice until the second week, and then it would notice everything at once.

Dana’s first instinct, because it’s everyone’s first instinct, was to post the sticker. “Chief of Staff. Wear many hats.” Her second instinct, thank god, was to ask what a Chief of Staff actually does before she hired one to do it. That question is the entire difference between what happened next and the version of this story where Dana hires a very expensive, very confused twenty-eight-year-old and blames them for it eight months later.

What a Real One Looks Like, Built on Paper

Here is the role Dana designed instead, and I am walking you through it because we built it as an exemplar for exactly this reason: not a template to copy-paste, but proof that the thing can be specified.

It does not run a function, and it does not manage her calendar. (Say that twice. Half the postings I read think those two facts are the job.) What it owns instead is the integration layer between Dana and her leadership team: the synthesis of everything happening across the company into one view she can act on, and the management of priorities once she’s set them, so she isn’t the one chasing her own tracker.

Then, the part that separates a role from a sticker: what this person decides without checking with Dana first. Which of the week’s competing priorities gets her time and which gets declined. Whether a fight between product and commercial gets resolved at the leadership-team level or has to climb to her. What makes the executive team agenda and what gets held back. Which requests for her time get accepted, declined, or redirected. Four decisions, real consequences attached to each, made without a permission slip. That’s not a coordination role. That’s authority, conferred on day one, in writing, which is the one thing corporate America keeps promising CoS hires “will develop over time” and then never delivers, the way a landlord promises to fix the dishwasher.

Week one, three things change, immediately, not eventually: Dana stops attending the Wednesday sync, because the Chief of Staff now runs it and reports back the one decision that came out of it. Dana hands over the planning tracker and stops personally chasing inputs from six department heads like an anxious substitute teacher. Disputes between product and commercial route through the Chief of Staff first, and only reach Dana if they can’t be settled below her. If Dana can’t feel the absence of three standing demands on her time by Friday, the role wasn’t designed. It was decorated.

And here’s the detail I want you to sit with, because it’s the one every bad posting is too embarrassed to include: the role has a clock. Ninety days, the exec meeting runs without Dana prepping it and the leadership team shows up with aligned recommendations instead of competing ones. Six months, collisions get caught and resolved before they ever reach her. One year, the company has an operating rhythm that doesn’t depend on Dana personally holding it together, and she is finally running the next stage of growth instead of babysitting the current one. There’s even a built-in expiration date on the role’s own necessity. It is not designed to make itself permanent by keeping the company dependent on it, which is more self-awareness than most departments manage in their entire lifespan, let alone one job description.

Compensation is a named number, stated plainly, not “competitive,” which is corporate for we’ll tell you after you’ve fallen in love with the role. And access is total: financial reporting, the board pack, function-level metrics, Dana’s inbox where she delegates it, observer status at board meetings. There is no information Dana sees that this person doesn’t, except the co-founder and personnel matters she specifically walls off. Notice what’s absent from all of it: anything a senior assistant could hold. That line is doing the whole argument’s work in eight words.

The Toolkit — Paid Edition

The Tool That Builds This Instead of Guessing at It

You do not need to reverse-engineer Dana’s exemplar from a newsletter, which would be like learning to fly a plane from the safety card. We built a tool that walks you through designing the role yourself, and it is, mercifully, harder to lie to than a founder alone with a blank Google Doc at eleven at night.

Ten questions, about thirty minutes, and you answer them in your own words, not a dropdown. It scores your answers, out of forty, across the ten, and then it does the part I’m genuinely proud of: it shows you the patterns in what you wrote, the priority gaps, and, credit where due, what you actually did well. Then it maps your answers against the nine functions that make up the role, so you can see exactly which of the nine you designed for and which you quietly skipped. It does not affect your score. It affects whether you know what you built.

Then it drafts the job description from your own answers, not a template with your company name pasted in, and hands you a PDF. Two honest founders will get two genuinely different documents, because they are, correctly, describing two different jobs. And if you haven’t done the thinking, it will not paper over that for you. It declines to flatter you into a polished document you don’t deserve yet. Most software wants you to feel good. This one would rather you be right.

It’s free. One per day, on purpose, because one honest answer beats ten lazy attempts at the same question: coulandgold.com/cos-jd

The Part Almost Nobody Uses, Which Is the Part You Should

Here’s what I actually want to talk you into, because it’s more useful for the people reading this who already have a posting live: the tool also runs in reverse.

If you’ve already written the job description, and you are confident in it (that particular flavor of confidence, the one right before someone hands you the bad news), you can paste it in instead of starting from the ten questions. We check it against the same nine-function definition and tell you, plainly, what you actually built. Not what you meant. What’s on the page. If it turns out you wrote an executive assistant role wearing a Chief of Staff nameplate, you will find out from a tool instead of from the hire’s exit interview eight months in, which is a much cheaper way to learn the same lesson.

I want to be clear about why this matters more than the flattering forward version. Building a role from scratch is where people are hopeful. Checking an existing posting is where people find out whether the hope was warranted. Most founders will never run the second one voluntarily, for the same reason most of us don’t reread our old texts to an ex. Do it anyway. coulandgold.com/cos-jd

Last Word

Every founder currently hiring a “Chief of Staff” believes, sincerely, that they know what they mean by it. Almost none of them can answer what this person decides on a Tuesday without checking first, and that question is the entire test. James Baker could have answered it in one sentence. So could John Podesta, whose door I sat outside of for years, watching people arrive with problems and leave with decisions that were now, unmistakably, his to have made. Ben Cafferty on Veep could not have answered it either, and the show’s joke is that nobody around him notices, which is the funniest and least fictional part of that entire series.

You do not need to hire Dana’s exact role. You need to know whether the thing you posted is a role or a sticker, and there is now a tool that will tell you in thirty minutes what would otherwise cost you a bad hire and a year to find out. Go find out which one you built: coulandgold.com/cos-jd. And if you want to see what a fully specified one looks like on paper, start to finish, that’s the exemplar: coulandgold.com/cos-exemplar-jd

Stop stickering jobs. Some of you are hiring assistants and calling them consiglieres, and the assistants deserve better, and so, frankly, does the word.

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