Chief of Staff- The misunderstood role
What does a Chief of Staff exactly do? This is these days the most frequently asked question in the founder groups. Now though I have never taken up that role, I have a few close friends who did, and I got a few learnings from them to demystify the role.
“It's a roller coaster journey - because each day of a COS journey can be dramatically different from the last. You are looking on the broader organisation context and going super deep on specific projects. You grow super rapidly as no other role gives you that degree of depth as well as breadth in a startup journey. You get direct line of sight into how the company leadership thinks, which helps you hone your own vision of the impact of any initiative, any project, any employee or customer will have on the broader organization growth.”
- Amrita, Scrut Automation
(a) what is the CoS role all about
Simply put, in an ideal scenario: a Chief of Staff to the CEO (or any higher executive, for that matter) is essentially the work shadow or the second brain of the executive. The CoS is expected to make the CEO’s life more productive, with a heavy strategic and execution muscle required on the job. It DOES NOT (or should not) mean picking up the menial tasks that a CEO is forced to do, nor is it a fancy-sounding Executive Assistant role (e.g. managing calendars, taking stock of emails etc.).
The COS works with the CEO on everything- be it brainstorming long-term strategy, tracking the execution of high-impact projects, setting up blue-sky projects from scratch, leading pilots for new initiatives, managing high-leverage processes in the org etc.
Having said the above, the Chief of staff can be of different types:
CoS to the founder: This person acts as the founder 2.O in this case
Special Projects: Firms sometimes hire CoS to own a few specific projects, for example- scanning new geographies and positioning the market entry
CoS to handle tactical and logistical stuff for the organization
It is important to figure out which one the organization needs and where one fits in.
(b) who is it for and whom to hire Given the high context switching required on the job, a great fit for the CoS role is someone who is genuinely better off at breadth than depth (to begin with) and has experience handling strategic and/or execution-heavy projects (depending on the stage of the organization).
Companies need to deeply analyze a few aspects before hiring a Chief of Staff:
What kind of role are you hiring for from the three above-mentioned (your *2, special projections or logistical stuff) and then figure out the skills needed accordingly
Considering the breadth of the role, usually, a generalist like a consultant fits well
Be clear about where will this role hopefully take the company and the candidate next. For a lot of candidates, this is usually a transitionary step to move to something more specialized.
For the candidates, it is important to understand what they want to get out of the role.
Akshay Chugh, who spent some time as the Chief of Staff at Last9, described the ideal output and company fit for him as below.
Stage of the company: 0 -> 1 in a product/company, preferably high-tech
Fit with the CEO: professional match (ideally repeat entrepreneur, product thinker, non-consulting persona for me to diversify my thinking), cultural and value system fit (v v important and something you should be able to intuitively feel)
Functional interest fit: Get to explore multiple functions and identify what my next role looks like
(c) what does the day-to-day look like The best answer here, in typical consulting style, is that it depends. The next realistic answer is whatever you want to make out of it.
Going on, I was upfront about my aspirations and expectations from the role with the CEO and he was more than happy to get that viewpoint from me. I typically worked with the CEO on agreeing on priorities of the month (based on company/product strategy, ongoing and upcoming fires, BAU work and some 10x ideas). The goal here was to be a thought partner to the CEO and agree on a priority list TOGETHER. What followed next (and may/may not work in your setup) was literally splitting the list between the two of us (based on our existing workload, fit with the project based on skills and interest). For my own sanity, I used to have a weekly check-in with him to quickly take a stock of where we are on the progress bar and discuss any blockers (but this can change based on the working styles of both parties). I did everything from product to finance to customer success to talent acquisition. - Akshay, ex-Last9
For most projects, the strategy and planning will have to be owned by the CoS, just like how it would be for a CEO to own a particular project. The role, however, changes slightly based on the size of the organization. If you are the CoS in a large-scale enterprise and one of your projects involves working with an existing leader (e.g. a BU head), you will also have to carefully navigate that relationship, and be the strategy and planning owner while not overshadowing the existing leader (a huge reason why large-scale enterprise CoS’ typically have many more years of experience than a startup CoS). The execution bit of the project can either be co-owned by the CoS or outsourced to a vendor/sub-team in the org. The CoS is then typically involved in tracking progress, solving blockers, streamlining the process, and moving on to the next high-leverage priority of the company.
The CoS role is truly great as a stepping stone into any function while allowing one to get your hands dirty with the organization’s real challenges. However, one should treat it as a stepping stone and a phase of optionality. Experience everything but with the mindset of getting into a specific role that is best aligned with your interests.
For companies and founders, it is a great way to double your capacity and also get a sounding board who has as much context as you.