Hi, I’m Elliott.
And welcome to “Musings from a 2x Chief of Staff,” a weekly essay for Chiefs of Staff and Operators.
Here’s essay #15.
Tl;dr
Chiefs of Staff don't fail because of skill. They fail because of fit - an avoidable problem if both the Chief and the principal are clear on what compatibility looks like.
In early 2023, I was snow-birding, working remotely in Puerto Rico for Ntropy, an early stage fintech company as their first Chief of Staff (CoS). Then, out of the blue, The Farmer’s Dog, reached out. The Series D, 550+ employee company wanted me to be their first Chief of Staff.
I said yes almost immediately.
But within months, I knew something was off. It wasn’t the people or the work itself, both of those were great. What was off was the noticeable gap between what I did best at the time and what my principal actually wanted. It was a gap I couldn’t close with effort alone, and a gap that both of us realized was missed during the recruiting process. Long story short: my tenure was shorter than expected, and for a while I couldn’t figure out what happened. I felt blindsided.
What I’ve come to understand since then is I wasn’t a bad chief of staff, I was just not the right fit at that time.
The gap I described before? It looked like this.
Not all chiefs are created equal
Everyone and their mother (Hi mom!) is hiring a Chief of Staff now. And for good reason. When the match is right, a CoS extends a principal’s capacity in ways no other hire can.
But the way companies recruit for the role is imperfect. In my experience, hiring managers optimize for skills and credentials while candidates evaluate opportunities based on company stage, brand and which VCs had invested.
That means no one is really talking about the elephant in the room: Is this Chief’s background and personality the right archetype for what we need right now? Will these two people be compatible as an operating pair?
Fit > Skill
The Chief of Staff role demands a level of intimacy with their principal that no other executive role requires. You're not just owning special projects: you're learning how they think, how they speak, how they make decisions, what bothers them, what excites them. In the role you become part therapist, part coach, part assistant, part operator. You are their second brain. And for that to work, fit is so much more important than skills.
Don’t get me wrong… skills still and do matter. But hiring managers need to first get clear on what the right archetype is, then narrow in on skills. And aspiring Chiefs need to do the same because skills don’t really matter when the relationship doesn't work.
Take it from me.
A tale of two CoS roles
I was in my element at Ntropy. The company was early-stage and everything needed to be built from scratch. You need 0-1? No problem.
I designed and ran the operating cadence that kept a fast-moving and remote team aligned. I co-led fundraising alongside the CEO. I stood up people operations. I built internal comms programs like All Hands. My weeks were filled with building and I was solving the kind of ambiguous operational problems that early-stage companies drown in without someone who thrives in that chaos.
I was in my element because that’s how I was wired then. I spiked on building and operating.
My time at The Farmer’s Dog was a different story.
The company was large and established, with hundreds of employees, and existing systems that were working well enough. My principal didn't need someone to build new operating infrastructure. They needed someone to join them on trips and meetings, take notes, keep him organized, and manage the flow of their team and relationships.
That was the gap I described earlier. My dominant strengths then skewed more operational, but he needed one with more experience in external-facing work.
That’s why getting clear on what type of CoS you need, as well as what type of Chief you are, is so critical to establish before you start the process.
I didn’t have the framework to help me determine fit before I took the role, and neither did they. So I built tools to help Chiefs and hiring teams determine the right fit. Check them out below.
The four Chief of Staff archetypes
Since that experience, I've spent a lot of time thinking about what makes a CoS partnership actually work, and I've come to understand four main archetypes that define how most Chiefs operate.
Those archetypes are outlined below:
This isn’t binary, or set in stone either. Someone isn’t only operational; they can have elements of other archetypes too. It’s more a matter of where they spike most.
The same is true for principals & execs. They can have one dominating need (external-facing) while also wanting other qualities too. Again, it’s a matter of prioritizing.
Archetypes are helpful for creating clarity but where we spike is a spectrum, and continues to evolves. That’s why I like this quadrant visual…it reminds me how my range can change.
The Tools to determine fit
If you’re gunning for the role, take this archetype quiz. It’s designed to show you where your center of gravity is. You’ll even get a handy-dandy graphic that illustrates where your center is.
For Hiring Managers, Exec Teams, Principals
If you’re thinking about hiring a Chief, and want to determine what type, then take this assessment. It asks you to get honest about what you actually need from this role and what type of Chief of Staff you need.
I encourage both employers and candidates to take these assessments and share their results during their screening interviews. Sharing is caring :)
Know your center of gravity
Most Chiefs have a dominant archetype: a center of gravity that defines where they do their best work. Knowing I was operational-dominant helped me understand why The Farmer’s Dog role didn’t fit back then. My exec prioritized a different archetype, and neither of us had the language to see it before I signed on.
Most companies, whether the hiring manager realizes it or not, also have a dominant need. When those align, the partnership works. When they don’t, both sides end up frustrated and the instinct is to blame skill or effort when the real issue was fit all along.
Chiefs of Staff don't fail on skill; that's properly screened for already. They fail on fit. And if something feels off in your role right now, start there before you question yourself.
Have you been in a role where the fit was off? I'd love to hear how you diagnosed it.