Welcome to Part 2 of the a16z series. If you missed Part 1 (Posts 1–5), go read those first. I’ll wait. I’m a Chief of Staff. Waiting for people to read things they should have already read is basically the job.
Below you’ll find three posts: Post 6 takes apart a16z’s archetypes, including the part where they suggest your EA is a natural CoS pipeline—four paragraphs after saying the two roles are completely different. Post 7 addresses their recommendation to call the role “whatever new title you dream up.” Post 8 dismantles their assessment framework, which is 2,000 words of scorecards followed by “also, trust your gut!” taped to the door like a corny kitchen sign from TJ Maxx.
I’ve spent eight posts on what a16z got wrong. Posts 9 and 10 go even further. Post 9 covers the multitude of ways an executive can destroy their Chief of Staff in under a week. (Some of them can do it in under a day. Overachievers.) Post 10 addresses the one thing about the role that is rarely discussed, but because it’s me, that ends now.
Both are waiting for you behind the paid tier. Come find us at the upgrade button. We saved you a seat. 🍿
POST 6: THE NONSENSICAL ARCHETYPES
Sixth in a Series Responding to a16z's "How to Hire a Chief of Staff"
a16z lists five “archetypes” where founders will likely uncover a great Chief of Staff. And I have to wonder whether they’re looking strictly in Fantasyland.
Consulting. Unconventional backgrounds. Former first ops hire. Public service. (Know what mine are? Project/Program Managers, Chief Communication Officers, and VPs of Marketing, but nobody asked me.)
And—I swear I’m not making this up—“Office Manager or Executive Assistant.”
Their reasoning is, “These individuals may not have had the title, but they’ve done the work.”
Now. Rewind four paragraphs in the same article, where a16z explicitly states that a Chief of Staff is not an Executive Assistant. (At least they got that right.) They even provide a helpful threshold: if 70%+ of the role is admin tasks, “you likely need an Administrative or Executive Assistant instead.” (And, hey, a16z, those titles are not, like, interchangeable.)
So the CoS is definitely not an EA. Unless they used to be an EA. In which case they’ve “done the work.”
I feel like I just walked out of a Christopher Nolan movie. I don’t get it.
Most Executive Assistants are extraordinary professionals. Full stop. Cross one at your peril. If you don’t understand that the executive admin and the facilities manager are the two most important people in any room where the CEO is present, you know nothing about people or management. The great EAs are indispensable. Value them. Compensate them. Respect them for what they do—don’t treat them as the JV squad warming the bench for a role they were never training for.
Are there EAs who could become strong Chiefs of Staff? Of course. Exceptions exist. But the two roles demand fundamentally different wiring—and I use that word deliberately. The core of what makes a great Chief of Staff isn’t teachable. It’s not a skill you pick up in a certification course. It’s a set of instincts around ego, ambiguity, pressure, and discretion that you either have or you don’t.
That’s the honest conversation nobody in the certification space wants to have. The gap between “this course will make you a better professional” and “this course will make you a Chief of Staff” is the gap between a piano lesson and a concert at Carnegie Hall.
Here’s what that means in practice: sharing the same air with an executive doesn’t qualify you for this role. Proximity isn’t preparation. Observing great judgment doesn’t give you great judgment.
Suzi and I get asked constantly—by aspiring CoS candidates, by executives eyeing a career pivot, by EAs who’ve been told they’d be “a natural,”whether they themselves have what it takes. For years, my honest answer was some version of, “I have no idea. I met you three minutes ago.” That’s not useful to anyone.
So, we built something to better answer the question and genuinely help people. The Coul & Gold CoS Readiness Assessment is a structured diagnostic that actually answers the question — not based on your resume or your references, but on the wiring, capabilities, and judgment the role requires. If you want to know where you stand, email us at [email protected].
Regardless, EAs and Chiefs of Staff require fundamentally different skill sets. Conflating them doesn’t just undervalue the CoS, it undervalues EAs by implying their role is a stepping stone rather than a destination. There’s a significant market of EAs who want to become Chiefs of Staff, and I don’t think it’s because they’re all dying to take on a job that is profoundly lonely and enormously stressful. They want the respect, the authority, and the compensation. That’s a recognition problem. Don’t solve it by blurring the job descriptions.
The “task-oriented with superb follow-through” language a16z uses to describe the EA archetype tells you everything about how they think about this role. Follow-through. Task orientation. Execution.
That’s not what makes a great Chief of Staff. What does? The ability to walk into a room of executives who outrank them on paper, read the dynamics in under ninety seconds, and command credibility by sheer force of judgment.
An EA optimizes a leader’s time. A CoS optimizes organizational execution. One protects your calendar. The other protects your blind spots. One ensures you’re prepared for the meeting. The other ensures the meeting never happened — because it only required pulling three people together for a ten-minute conversation, none of whom would have been on the original invite.
Different muscles. Both valuable. Not interchangeable. And not a career pipeline.
POST 7: CALL IT WHATEVER YOU WANT (JUST KIDDING. SERIOUSLY. PLEASE DON’T.)
Seventh in a Series Responding to a16z's "How to Hire a Chief of Staff"
a16z suggests that if the title "Chief of Staff" feels too "glamorous," founders should consider alternatives.
Their suggestions:
"Special Assistant to the CEO”
"Director of Internal Ops"
"Head of Business Operations"
"Office of the CEO"
Or—and I am quoting directly— "whatever new title you dream up."
Whiskey. Tango. Foxtrot.
Picture yourself walking into a leadership team meeting as the "Special Assistant to the CEO." The CFO is across the table. The CTO is checking Slack. The VP of Sales just came in hot from a blown deal and is emotionally available for absolutely nothing. And you, the Special Assistant, are about to tell all of them the new HR policies are wreaking havoc and need to change.
How's that going? It's not. Because the moment you walked in with "Special Assistant" on your badge, everyone in that room mentally filed you under "not my problem." You could have the sharpest strategic mind in the building and it won't matter. They stopped listening at "assistant."
But hey, you assisted. Specially.
You know who understood the power of a title? Gerri Kellman on Succession. The moment she became interim CEO, the dynamic in that building shifted because the title signaled authority the room had to respect. Take the title away and she's back to being the person Logan's kids condescend to between nervous breakdowns.
Meanwhile, Dan Egan on Veep collected titles like frequent flyer miles: "Director of Communications," "Senior Strategist," "Senior Advisor," "Whatever Selina Needed That Week." Not a single one of them gave him actual power, because nobody respected the role behind them. He had business cards for days and influence for approximately twelve seconds flat.
Titles may not dictate what you do day-to-day, but they absolutely dictate your salary and your future earning power. I don’t like it, but that’s the world we live in. A "Director of Internal Ops" and a "Chief of Staff" can do the exact same work (although they absolutely shouldn’t!) and the Chief of Staff will out-earn the Director by tens of thousands of dollars, in the role and in every role that follows. Compensation benchmarks don't care about your job description. They care about your title.
It gets worse. The barrier to entry for the Chief of Staff role is the title itself. If you haven't held it, most organizations won't believe you can do the job, regardless of what you actually did. So when you call someone "Special Assistant" instead of "Chief of Staff," you're not just undermining their authority today. You're kneecapping their career trajectory for the next decade.
You cannot give someone the responsibility of a Chief of Staff and strip them of the title. The title is the authority signal. It tells the organization: this person operates at the executive level. This person speaks for the CEO. This person is not your assistant's assistant.
"Director of Internal Ops" says: I have a dashboard on Confluence that no one reads.
"Head of Business Operations" says: I own a function, a dashboard, and an existential crisis about my org chart placement.
"Special Assistant" says: I'm senior. I'm strategic. I'm… why is everyone looking at me like I'm here to take the lunch order?
"Chief of Staff" says: The President of the United States trusted this role to coordinate the entire federal government.
That's not glamour. That's gravity.
If the title feels too big, the problem isn't the title. It's that you don't yet understand the role. And maybe that's the conversation you should be having before you post the job.
POST 8: YOU CAN’T SCORECARD YOUR WAY TO TRUST
Eighth in a Series Responding to a16z's "How to Hire a Chief of Staff."
a16z wants you to hire your Chief of Staff using a framework called a MOC: Mission, Outcomes, and Competencies.
Scorecards. Repeatable interview questions. Case studies. Stage-by-stage assessment rubrics. A visual leveling chart with five tiers and three orientations.
It's rigorous. It's thorough. It's the exact process you'd use to hire a VP of Engineering.
And that's the entire problem.
I'm not anti-framework. Suzi and I are building several. A framework for hiring a Chief of Staff isn't a wrong instinct—in fact, we think it's a necessary one. But a framework only works if it measures the right things. When your foundation is wrong—when you've categorically misidentified what the role actually is—everything you build on top warps accordingly. The MOC isn't flawed because it's structured. It's flawed because it's structured around the wrong definition of the job.
a16z calls this "ultimately a competency-based hire." It isn't. A Chief of Staff is, above all else, a trust-based hire. And a16z appears to know this, because at the very end of their assessment section—after 2,000 words of frameworks and rubrics—they add, "Don't underestimate chemistry" and "if it doesn't click in the first few conversations, move on."
They built an entire assessment cathedral and then taped a handwritten note to the door that says "also, trust your gut." Like those signs at TJ Maxx that say Live, Laugh, Love — except this one says Live, Laugh, Hire. And it costs you $180,000 a year plus benefits.
Now let's talk about chemistry, because every time I hear someone use it as a hiring signal, it sounds like they're casting a sequel to The Notebook. Chemistry is not a legitimate hiring methodology. Just because a candidate is oozing chill vibes and would be great to grab a beer with, doesn't mean they should be your Chief of Staff. Unless those chill vibes are exactly what you want when you're facing massive budget cuts and have to make excruciating staffing decisions. ("Hey, I know we have to lay off forty people, but have you tried breathwork?")
Chemistry is only a useful flag if it's so far off, your skin crawls when they walk in the room. Short of that, ignore it. What you actually need is a conversation designed to surface how a candidate navigates ambiguity, pressure, ego, and the moments where every available option is bad and somebody still has to choose.
A scorecard can't tell you any of that. Neither can a case study. Neither, it turns out, can 2,000 words from a16z.
Here's what the MOC framework can't measure: whether your CoS will walk into your office, close the door, and tell you something you genuinely don't want to hear—because they've correctly identified it as the thing you most need to hear. There's no rubric score for that. No case study surfaces it. Not even one from the prestigious a16z.
Leo McGarry on The West Wing knew exactly where all the bodies were buried, which fires were actually fires, and—most importantly—which ones the President had started himself. Run him through the MOC framework and you'd probably advance him to round two. Then he'd say something the hiring committee didn't want to hear, and they'd politely thank him for his time.
Somewhere, a very qualified candidate who scored a 4.8 on "stakeholder alignment" just got the job instead.
The person who will tell you you're wrong when it matters most rarely looks like a slam dunk on a scorecard. That's not a framework outcome. That's the whole damn hire.
I've spent eight posts on what a16z got wrong. Posts 9 and 10, behind the paid tier, go even further. Post 9 covers the multitude of ways an executive can ensure complete failure for their CoS in under 7 minutes flat. Post 10 addresses the one thing about the role that is rarely discussed, but because it’s me, that ends now.
Both are waiting for you behind the paid tier. If you've read this far, you already know this is a conversation worth finishing.
Come find us at the upgrade button. We brought the popcorn. 🍿
And if our paid tier is beyond your budget, you're still in the right place. I'll be back in mid-April breaking down how to actually read a CoS job description which, if a16z's hiring guide is any indication, is a skill in desperately short supply.
