Leo's Letter #42 // Chief of Stuffs
What do you do when you do a little bit of everything?
Hey, it’s great to have you.
I’m writing this while funemployed.
And am I glad to have a short break in between jobs (unlike last time when I went straight from one job to another)!
After doing nothing but relaxing for a few days and then spending time with people that mattered, I took a look in the mirror and reflected on my experience over the last year. Think of this as the closure to what I previously wrote on the most fun I’ll never have again.
P.S. - have a great Thanksgiving! I for one am super grateful.
Reach out to catch up over the next few days!
Definitions
Chief of Stuffs: also known as IT person, ghostwriter, and mafia game host amongst many of the other hats I wore as a Chief of Staff (CoS) for the crypto team at a fintech company.
During that time, I also participated in communities for CoS run by On Deck, the Chief of Staff Network, and Primary Venture Partners.
I’m writing this to reflect on the experience, going into:
What the role is about
Why one should take this role
Observations on the job
A generalist and specialist at the same time
Every CoS role is a little different and my experience is only one data point.
However, regardless of the specifics, the purpose of the CoS is to provide leverage to the Principal (the manager of the CoS).
This can come in many forms. My responsibilities fell into the below buckets:
There’s A LOT to do. And often at the same time.
They say that the CoS role is a generalist role; however, I’d say that all CoS are masters at organization. Imagine having to zoom in and out from the most strategic work to the most tactical tasks - often multiple times per day.
For example, a day may involve running some meetings as the project manager, researching a new area for a business case, and then suddenly getting a call from your Principal asking for a draft of a memo to send to the Executive team on a recent market development… combined with responding to multiple pings from team members asking where things are / how they work - how fun!
The CoS is a figurative juggler of many balls.
CoS is the new management training
Move over Harvard Business School case studies, in this role we learn by doing!
A CoS role is the fast-track to learning management regardless of seniority:
Junior - learn directly under the Principal
Mid-level - get broad exposure to then specialize
Senior - lead a function
Looking at the Chief of Staff Leveling Framework, I fell into level 3:
Although I didn’t end up specializing within the company (instead moving to another firm), I did see three potential areas to double down on:
Strategy - competitor and market analysis, business casing, OKR setting
Business operations - building and managing processes, program and project management, and internal consulting
People operations - hiring, performance reviews, promotion frameworks, employee engagement, and whatever can be done as an HR department of one
From what I gathered, a mid-level CoS has the potential to transition into a Director or VP-level role within these areas (or others not mentioned).
Specialization can happen naturally: the business need for such a role would match with the CoS’ current duties and performance within the function. Who better to fill the role than the person already performing it and ready to double down - while having context of the entire organization?
Five additional thoughts
#1 - breaking in.
I’ve seen three common ways to become a CoS:
Transition from an Executive Assistant, where you’re already helping your Principal with confidential information
Transition internally as the organization grows and needs more cross-functional collaboration
Enter as a “high-potential generalist” after two years of investment banking or consulting experience
#2 - a CoS is the product manager of internal processes.
The CoS may run company routines like all-hands and leadership team meetings, performance review processes, own employee onboarding, etc.
Credits to Josefin Graebe for sharing this insight in her session with On Deck!
#3 - a mid-level CoS is the bridge between management and employees.
This is a unique seat where the CoS can simultaneously:
Sit in the room where decisions are made and access privileged information
Relate to employees both in work and outside of work (less of an age gap)
#4 - if there’s no Executive Assistant, you are the Executive Assistant.
Who else will help the Principal schedule meetings? Order equipment for new employees? Handle office maintenance?
Buyer beware
#5 - a lot of the work is behind the scenes.
A good portion of managerial work is administrative. The CoS may often do this work on behalf of the Principal to give him/her leverage for other tasks
If you’re looking for a high-profile, “C”-level role, please humble yourself
Until Next Time
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