The Ash That Remains After Burning Down a16z's "How to Hire a Chief of Staff" | Part 3 of 3

Note: We apologize and had a technical difficulty with this post. Tomorrow, you’ll receive Suzi Coul’s masterful “Nine Dimensions of a Leader’s Operating Signature.” We hope you’ll consider joining us as a paid subscriber to read it in full.

This is the last installment in this series. You’ve now heard from me four times in one week. Please don’t expect that on a regular basis. But you can expect it when I get fired up (which happens more frequently than you’d think). If I’ve got something to say, you can take great comfort in knowing that I’m absolutely going to say it. And you’ll get greater access to me than anyone else because you’ve generously contributed to this effort.

Please respond with comments, questions, or any other ideas you’d love to see us address in the weeks and months ahead. Thank you!

POST 9: HOW TO KILL A CHIEF OF STAFF IN UNDER A WEEK

Ninth in a Series Responding to a16z’s “How to Hire a Chief of Staff”
(Paid Subscribers Only)

This post is for every CEO, founder, and executive who has ever hired a Chief of Staff and watched it fail.

I have news. It wasn’t them.

a16z spent 4,000 words telling you how to hire a Chief of Staff. Archetypes. Leveling frameworks. Assessment rubrics. A visual chart so detailed it looks like it was designed by someone who peaked in AP Art History.

What they never told you is how to avoid destroying the role in its first five days. Which is a bit like selling someone a Steinway grand piano and forgetting to mention you shouldn’t leave it in the rain.

This is the gap in the article that will cost you more than any bad archetype or wonky leveling framework. Because it doesn’t matter if you hire the perfect candidate from the perfect background with the perfect score on your precious MOC. If you botch the introduction, the role is dead before the business cards arrive.

 Here are five ways you’re killing this role. I’ve seen every one of them. In some cases, I was the one getting killed.

1. THE ANNOUNCEMENT THAT TANKS AUTHORITY IN A SINGLE SENTENCE

a16z says the CoS should be “part of the executive team” with “a seat at the table.” Great. That’s true. Then what happens?

Monday morning. All-hands email. “I’d like you to meet [Name], who’s joining as my Chief of Staff. They’ll be helping me stay organized and supporting the leadership team.”

Helping. Supporting. Organized.

You just told your entire company this person is your assistant. In writing. With a distribution list. Congratulations. You have now spent $175K on a role you torpedoed in a single sentence.

Your CFO read that email and mentally filed your new CoS under “not my peer.” Your CTO read it and thought, “Another person between me and the CEO.” Your VP of Sales didn’t read it at all because it didn’t have a revenue number in the subject line.

The announcement is the role. Get it wrong and there’s no reset button. This isn’t a role where you can quietly correct course over the next quarter. First impressions in organizational hierarchy are permanent. Ask anyone who’s ever been introduced as “junior” anything.

What you should have said: “[Name] will be coordinating across the leadership team with my full authority and confidence. Assume their requests have my backing.”

That’s not a suggestion. That’s a mandate. And your CoS needs a mandate, not an introduction.

2. THE “RIGHT HAND” INTRODUCTION THAT MAKES YOUR C-SUITE HEAR “ASSISTANT.”

a16z describes the CoS as someone who “acts as a proxy when needed.” Proxy is fine. But here’s what happens in practice: CEOs walk into a leadership team meeting with their new CoS and say, “This is my right hand.”

You know what every executive in that room hears? “This person works for the CEO, not with us.” The CoS is now an appendage of the CEO instead of an integrating force for the organization.

In Succession, Tom Wambsgans spent four seasons as a “right hand;” first to Shiv, then to whoever was winning. And the entire cast treated him as exactly what that positioning communicated: someone who existed in relation to someone else, never on his own authority. The moment he stopped being a right hand and started operating with his own leverage, the dynamic shifted entirely.

Your CoS is not your right hand. Your CoS is the person who makes sure every hand in the organization is doing what it’s supposed to be doing.

3. THE ORG CHART BURIAL

a16z says the CoS should be “working under a single Executive.” Reporting to the CEO? Fine. Buried under the CEO on the org chart between the EA and the office manager? Fatal.

Where you place the CoS on the org chart communicates everything. If they’re visually below the C-suite, they are below the C-suite. No amount of verbal authority overrides what the org chart says. People look at org charts the way they look at seating arrangements at a wedding: your placement tells everyone exactly how important you are to the people who made the chart.

Your CoS should sit at the CEO level, not below it. The White House doesn’t bury the Chief of Staff under the cabinet secretaries. Corporate America shouldn’t either.

4. THE SCOPE DUMP THAT TURNS A STRATEGIST INTO A PROJECT MANAGER

a16z lists “leading special projects” as a core responsibility and then adds, in parentheses, “But as we point out above, this won’t be their whole job.”

It’s adorable that they think a parenthetical will prevent scope creep.

Here’s what actually happens: Week 1, you hand your CoS a strategic initiative. Week 3, you add a “quick” operational project because “nobody else can own it right now.” Week 6, they’re managing three special projects, running your staff meeting, and somehow also coordinating the office move because “it’s just logistics.” By month three, your Chief of Staff is a project manager in a nicer office with a fancier title and a growing existential crisis about what they were actually hired to do.

This is how the “catch-all” happens. Not because CEOs are malicious. Because they’re overwhelmed, and the CoS is the one person who will say yes to anything because they’re still trying to build trust.

Protect the scope like you’d protect the budget. Because if everything is a CoS priority, nothing is.

 5. THE “FIGURE IT OUT” ONBOARDING

 This one is personal.

a16z suggests the CoS should “understand the nuances of the business within their first 90 days” and recommends a “listening tour.”

Fine. But a listening tour without organizational endorsement is just a confused person booking meetings nobody wants to take. If no one has explained to your leadership team who this person is, what authority they carry, and why they should give them an hour of their time, your CoS isn’t on a listening tour. They’re aimlessly wandering the building like Tom Hanks in Cast Away having lost his beloved Wilson volleyball to the sea.

I once had a boss tell me on Day 1, “Go meet with whoever you want.” He thought he was empowering me. He was abandoning me. He hadn’t communicated my authority to anyone. He hadn’t set up a single meeting. He hadn’t told the leadership team I was coming. I was a guest at a party no one knew I was invited to, which you can imagine was pretty awkward.

That’s not onboarding. That’s waterboarding.

Before your CoS walks through the door, you should have mapped their first 30 meetings. Not with you. With your CFO. Your head of product. Your most difficult board member. The VP who’s been quietly running a shadow government from the corner office for the past year.

And every one of those meetings should happen because you personally told each person, “This is happening. Take it seriously.” 

a16z gave you a framework for hiring. They forgot to mention that how you introduce, position, onboard, and protect the role matters more than who you put in it.

You can hire the perfect Chief of Staff. And destroy them in an hour.

Please don’t.

POST 10: THE LONELIEST ROLE IN THE BUILDING

Final Post in a Series Responding to a16z’s “How to Hire a Chief of Staff”
(Paid Subscribers Only)

This last post isn’t for CEOs. It’s for the Chiefs. The people doing the job.

I’ve been thinking about this for several weeks, ever since I met a young woman who couldn’t have been older than 30. She had recently left a Chief of Staff role because she couldn’t take it anymore. She looked emotionally exhausted—haunted in a way that reminded me of veterans who come back from war, scarred in ways the rest of us will never fully understand. She wanted to meet me to ask whether she’d done something wrong, and whether this is typical: to feel so completely flattened by a job.

a16z describes the Chief of Staff as “the control tower,” the person who “keeps the CEO focused, the team aligned, and the priorities moving. Without them, things fall apart.”
They’re right. (That’s the first time I’ve said that in ten posts and we should all take a moment.)

But here’s what they left out: what it actually feels like to be that person.

Nobody writes about this part. Not a16z. Not the certification courses. Not the LinkedIn thought leaders with their tidy frameworks and clean little diagrams. Because the truth about the Chief of Staff role isn’t clean. It’s not tidy. And it doesn’t fit in a leveling chart.

So let me say it plainly, for every Chief of Staff who has never heard anyone with a platform say it out loud:

This is the loneliest role in the building.

Even if you have a lovely, thoughtful boss—kind, appreciative, someone who actually understands what you do—you still carry the CEO’s secrets. You carry the company’s secrets. You sit in rooms where decisions get made that will affect people’s livelihoods, and you cannot tell a single soul. You go home and your partner asks how your day was and you say “fine,” because the real answer would take three hours and a security clearance.

Your authority is borrowed. It comes from the CEO, and it can evaporate in a single meeting if they fail to back you up. You spend months building credibility with the CFO, and then the CEO casually overrides you in front of the leadership team and you’re back to square one — except now everyone was watching.

a16z says the CoS should be “deeply trustworthy” and handle “sensitive information with total discretion.” They’re describing a job requirement. They’re not describing what it costs.

Discretion isn’t a skill you perform. It’s a weight you carry. Every day, in every conversation. You know who’s about to be let go before they do. You know which executive is underperforming before the board does. You know the real reason the strategy shifted and you cannot explain it to the people whose work just got thrown out because of it.

And you do all of this without credit. a16z calls the role a “force multiplier.” That’s a polite way of saying you make everyone else look better and nobody knows it was you. Your wins are the CEO’s wins. Your interventions are invisible. The meeting that didn’t go sideways, the reorg that didn’t blow up, the executive conflict that got resolved before it metastasized—nobody sees the save. They only see the disaster when you miss one.

I’ve been interviewing Chiefs of Staff—overwhelmingly women—for the better part of two years. Over 150 conversations. And the thing that comes up more than role confusion, more than scope creep, more than the EA comparison, is the extreme isolation.

They don’t feel seen. Not by the CEO, who is often too consumed by their own pressures to notice. Not by the leadership team, who views them with a mixture of curiosity and suspicion. Not by the staff, who can’t quite figure out what they do but senses they have the CEO’s ear and keeps a careful distance.

The Chief of Staff sits at the center of the organization and is somehow the most peripheral person in it.

And it’s arguably worse for women. Women Chiefs of Staff get assigned administrative tasks their male counterparts simply don’t. They get called “helpful” when they should be called “strategic.” They get confused with the EA—not because the roles are similar, but because the organization defaults to its assumptions about what women in proximity to power must be doing.

One woman told me she was introduced by her CEO as “the person who keeps me organized.” She’d restructured two departments and saved the company from a compliance disaster that would have cost them millions. But she “keeps him organized.”

a16z says this is “ultimately a competency-based hire.” But they never mention that the experience of the role is profoundly shaped by gender—and that ignoring this means your frameworks will produce systematically different outcomes for men and women in the same position. You can’t write a hiring guide for a role that women disproportionately hold and skip over that. It’s like writing a guide to deep sea diving and forgetting to mention air tanks.

Here’s what I also know, from those same 150 conversations: this assumes you have a strong leader at the helm. Most executives aren’t. They were exceptional individual contributors who got promoted because of their performance, with nobody sitting them down to explain that being a rockstar data analyst does not in any way prepare you for people management. Or they’re an unchecked founder who generates ideas faster than a stock ticker but has no sense of—or empathy for—the people who actually have to execute against those decisions.

So here’s what I want to say to every Chief of Staff who has read this series and felt something, and especially to the woman who showed up to our meeting looking like she had PTSD:

You’re not crazy. The role is hard because the role is hard as hell, not because you’re doing it wrong. The loneliness is structural, not personal. The invisibility is a feature of borrowed authority, not a reflection of your value. And the fact that you show up every day, carry what you carry, and still find a way to make the organization better and the people around you shine brighter—that is not a competency on a scorecard. That’s something far more rare.

You deserve better than a 4,000-word article that treats your role like a two-year internship with a demotion path to Sales Ops.

Suzi Coul and I built the Coul & Gold Briefing for the person reading this right now. The one who Googled “is the Chief of Staff role supposed to feel like this” at 2 am and couldn’t find an honest answer.

Here’s your honest answer: yes. It feels like this. And it doesn’t have to.

Every issue. Every week. Frameworks that actually measure what matters. Experience from someone who’s been in your seat. And the knowledge that you are not, in fact, alone—even when the role makes you feel like you are.

No staircar. No fava beans. No lightbulb emojis.

Just the work. And the people who understand.

See you in two weeks,

Rachael

​​​​​​​​​​​​​​​