Over the next several days, I’m taking a16z’s deep dive on the Chief of Staff apart on LinkedIn. But as a subscriber of our newsletter, and to show our deep appreciation for joining us, I’m giving you full access to my entire assessment now, including five posts that won’t ever appear on LinkedIn (they arrive in your inbox tomorrow and Friday). Three will go to all subscribers. The other two will go to paid subscribers only. So if you want to join our Founders Circle at $99/yr for life, now’s the time — you’ll get the full series, plus the five posts LinkedIn will never see. (And you can be assured, I’m saving the most brutal assessments for you!)

a16z just published an expanded framework for how to hire a Chief of Staff.

It’s thorough. It’s well-researched. It has tables.

It’s also going to set a lot of people up to fail.

In January, a16z published an article about hiring a Chief of Staff. Instead of refining it, they recently expanded it — adding leveling rubrics, archetypes, and assessment frameworks that are impressively detailed and, in several critical ways, wrong.

It might seem like I’m harping on a16z, but there’s a reason for it: when they publish something, founders treat it like the Ten Commandments came down from Sand Hill Road on a stone tablet. That’s a testament to their influence. If they even breathe in the same direction of a start-up, people notice and money miraculously flows. What they think matters. A lot. But influence without accuracy on this particular topic is going to produce a lot of expensive, well-intentioned organizational chaos.

It reminds me of that moment in Succession where Shiv borrows a twenty-dollar bill from Greg to use a hospital vending machine. The Roys are billionaire royalty — people who have had authority their entire lives and have no idea how everyday things actually work. And when it comes to the Chief of Staff, the same pattern applies. The scaffolding looks impressive. And a16z makes some remarkably savvy bets. But on this topic, the foundation is styrofoam.

The Chief of Staff role originated in the military, then morphed into a civilian role in the White House, but it is one with the same senior authority, the same influence, the same weight. Somewhere in the early aughts, corporate America decided it wanted something similar and then cannibalized it, stripped the authority, slapped on a job description, and served it with some fava beans and a nice chianti.

Now we have a role that nobody can seem to agree on. And well-intentioned frameworks from well-intentioned people —inside and outside the Chief of Staff community— are compounding the confusion, not resolving it.

POST 2: COMPLEMENTING AN EXECUTIVE ISN’T THE JOB

Second in a Series Responding to a16z’s “How to Hire a Chief of Staff”

“First, a good CoS should complement you.”

That’s the opening line of advice in a16z’s Chief of Staff guide. The very first thing they say to founders about this role. And it’s already going sideways.

Then it just gets worse.

“A technical founder might hire a CoS with a strong finance or operations background; or a visionary CEO will hire a day-to-day operational grinder.”

I feel like I’m in an Amazon Warehouse. Match the boxes. Ship the hire. Done.

Except that’s not a Chief of Staff. That’s a gap-filler with an inflated title — like a seat-filler at the Oscars who’s there to make the theater appear packed with people paying rapt attention, instead of the reality of a bustling lobby where celebrities actually are. Both of them are complete fiction.

The Chief of Staff doesn’t exist to cover your weaknesses. They exist to protect you from risks and calamities coming down the pike. (Hyperbole? Yes. True and accurate? Also yes.) They’re also there to extend your presence across the entire organization. They’re in the room you can’t be in, and, if positioned correctly, everyone in that room knows they speak with your full authority. They’re making the call you don’t have time to make. They’re having the conversation you shouldn’t have because it would blow up if you did.

Your CoS doesn't need to be your opposite. They need to be so deeply trusted that they can walk into any room in the building and command it as if you're standing right behind them.

That’s not “complementary skills on a matrix.” That’s trust. Deep, earned, battle-tested trust. The kind that takes years to build and about twenty-three seconds to destroy.

Extending your presence is only one-third of the job. And here’s the part that genuinely stunned me: The other two-thirds —integrating your leadership team and advocating for your staff— never appear in this article.

Not once. In 4,000 words.

That’s like writing a cookbook and forgetting to mention heat.

It’s also worth noting that the two authors are talent recruiters. To the surprise of no one, I have a lot to say about this. We’ll have more about it in future briefings, but suffice it to say, an overwhelming number of recruiters do not understand the subtleties and nuances around the chief of staff role. I won’t blame them for it — executives and founders hijacked the title because it sounded cool and never built the infrastructure around it. The recruiters are only following their lead. But they’re a big part of the problem.

When you’re scoping this role, don’t ask “where am I weak?”

Ask: “Who do I trust to walk into any room in this building, read the room in under ninety seconds, and make a call I’d be proud of?”

That’s the complement that actually compounds.

POST 3: THE EXPIRATION DATE

Third in a Series Responding to a16z’s “How to Hire a Chief of Staff”

a16z writes, “A CoS isn’t a forever role. In most cases, it’s a 2–3 year commitment.”

They then explain that after two years, you should “consider how you can support them in their next step.” 

Say what now?

Because apparently the Chief of Staff is a temp with a strategic plan and an expiration date printed on their forehead.

It gets better. They say the CoS “can use this role as a springboard into another part of the organization.” They suggest your CoS might “go on to lead” in Finance, Marketing, or Operations. They even suggest your CoS could “fit in well under a particular leader, such as your CRO or VP of Sales, to run Sales Ops.”

They took the most senior coordination role and mapped out a demotion path.

And then, my personal favorite, they call the experience “a free MBA.” I needed to sit with that for a second. With a martini. Because unless an MBA involves studying politics, power, and people (and the last time I checked it involved accounting, statistics, and data analytics), a chief of staff isn’t a crash course on business administration.

Tywin Lannister didn’t rotate his Hands every two years and suggest they try a stint in Dorne running regional partnerships. The Hand of the King held the role because it was the role. It wasn’t a gap year with a fancy pin.

When you design a role with a countdown clock, you get countdown commitment. By month fourteen, your CoS is networking for their next gig. By month eighteen, they’re phoning it in. By month twenty-two, they’re helping interview their own replacement while updating their LinkedIn in the bathroom. You built that. Not them.

Here’s what a16z gets right: burnout is real. The intensity of this role is no joke.

Here’s what they get catastrophically wrong: the solution to burnout isn’t an expiration date. It’s organizational support, clear scope, and a CEO who doesn’t treat their Chief of Staff like a gym membership they cancel every January.

The Chief of Staff role isn’t a pit stop. It’s a pinnacle. And the people who are best at it know that.

POST 4: THE STEALTH COO

Fourth in a Series Responding to a16z’s “How to Hire a Chief of Staff”

I almost did a spit take. 

In describing what a Chief of Staff does at a 150+ person company, a16z writes: “In practice, this is a stealth COO role.”

Double oy vey.

They are telling founders to hire a Chief of Staff and then secretly make them a Chief Operating Officer without the title, the comp, the authority, or —and this is important— the job description that would have attracted the right candidate in the first place. I don’t know whether to laugh or cry. But hey, at least they’re consistent. 

This is pure Amy Brookheimer energy. If you watched Veep, (and if you haven’t, you should) Amy did everyone’s job — campaign manager, Chief of Staff, policy director, crisis manager, emotional support human — and got a different title every season while doing the same impossible workload for roughly the same terrible pay. When someone finally asked her what her actual job was, the answer was basically, “Yes.”

That’s not a career path. That’s an HR violation with Emmy-winning dialogue.

A Chief of Staff is not a COO. A COO is not a Chief of Staff.

One is a line function that runs operations. The other is a coordination function that integrates the organization and extends the executive’s capacity to lead. One owns the machine. The other makes sure all the parts of the machine are talking to each other and nobody’s quietly building a competing machine in the basement that Matthew Broderick will get to use in War Games: The Return.

When you blur those lines, two things happen:

1. Your CoS drowns in operational ownership they were never scoped or compensated for.

2. Your actual COO (when you finally hire one) walks into a turf war on Day 1 and immediately starts wondering if this job posting was a trap. Which is the secret to every successful CoS and COO relationship (not).

And a16z knows this, because earlier in the same article they write that a CoS “is not a substitute for a different functional leader, such as a Head of Operations.”

So which is it? Not an ops leader, or a stealth ops leader?

Pick a lane. Or at least pick a paragraph.

You can’t have it both ways. Well, you can, if you’re writing a VC newsletter from the likes of Sand Hill Road. But you can’t if you’re actually running a company and expecting someone to perform two completely different senior executive functions for the price of one.

 POST 5: THE LEVELING LADDER

Fifth in a Series Responding to a16z’s “How to Hire a Chief of Staff”

a16z built a five-level framework for the Chief of Staff role. Here’s what it looks like:

I can’t figure out whether this is a “Choose Your Own Adventure” or choose a video game where you level up by collecting enough special projects, surviving enough all-hands meetings, and resisting the urge to bring duct tape and a pair of boxing gloves to every executive team discussion. 

The Chief of Staff role doesn’t work like a software engineering career ladder. You don’t start as a junior CoS grinding your way to senior CoS.

This isn’t Candy Crush. There are no levels. There is the role.

At Level 1, a16z says the CoS “helps with communications, decks, and meeting preparation” and “operates with regular oversight.”

Did James Baker — Reagan’s Chief of Staff and one of the most consequential political operators in modern American history — need regular oversight? Did Leon Panetta need to check in with someone before he righted a sinking Clinton White House?

a16z isn’t even describing an Executive Assistant. It sounds more like a receptionist. A truly outstanding one. But it is categorically not a Chief of Staff. And calling it one does a disservice to both roles.

A Chief of Staff walks into an organization on Day 1 with the authority and mandate to coordinate the leadership team. Not because they’ve “learned the Executive’s working style.” Because the CEO stood in front of the entire company and said: this person speaks on my behalf, operates at my level, and has my full confidence.

If your Chief of Staff needs to “level up” to be taken seriously, you didn’t hire a Chief of Staff. You hired someone to earn a title they should have been given.

As the Bluths would say, “There’s always money in the banana stand.” The value was there the whole time. Stop burying it under five levels of corporate gamification.

Tomorrow, the additional posts. Stay tuned.