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What does a Chief of Staff do, anyway?
The most important role of a Chief of Staff is administering the operating model. This means being responsible for crafting each touchpoint and supporting teams on every deliverable. While Chief of Staff roles encompass many things - gatekeeper, project manager, air traffic controller, connective tissue, senior administrative assistant, shadow CEO - at their core they fulfill these functions in service of the operating model.
To understand how the CoS administers the operating model, it’s important to have the context of the job as a whole, which can be broken down into three pillars: Executive Support, Team Support, and Special Projects.
A great CoS is a force multiplier for a CEO because they act as a second brain. CEOs can remain on the highest-level objectives while still having coverage of the details. If you haven’t experienced this kind of support, it can be hard to understand how valuable this is.
Picture having an AI (yes, eventually this role will and should be replaced by tech), that collects information from across the organization. They look at the data every day. They embed with teams. They are in all your meetings. They read all your emails. They have visibility into every detail.
Now picture them using it to improve how you show up at work. Some examples -
Every morning, they deliver a packet that contains your schedule for the day and a prep doc for every meeting, complete with status updates, team dynamics and data points to consider, and talking points.
At the beginning of every week, they give you a rundown of input and output metrics, what’s changed, and what you need to pay attention to.
They manage your inbox, sorting it into what you should respond to and handling everything else.
They sit in every meeting, helping to facilitate the right conversations.
They hold you accountable for all the stuff you say you’re going to do - even the soft skills stuff you’re working on with an executive coach.
If you hire someone who is values and mission-aligned, and who really believes in you as a leader, a CoS can have a profound impact on the amount of work you can get done, as well as how you show up, are perceived, and grow as a leader.
Chiefs of Staff support teams primarily by designing and administering the operating model. They also ensure teams have the data needed to execute by pollinating key information across the organization and embedding with teams to drive outcomes as the CEO would but that work is pretty straightforward and is similar to what I described in executive support. So let’s talk operating model.
Administering the Model
Administering the model has three distinct parts - Documentation, Alignment, and Tracking.
In this stage, the CoS puts pen to paper and creates a program for the year ahead, outlining touchpoints for the operating model, which is ultimately just a series of moments for leadership and teams to plan, execute, and regularly review our strategy at a cadence that allows the strategy to materialize. It generally includes (as outlined in my last post):
Annual Planning: Time for leadership to create annual strategy and annual financial plan.
Quarterly Planning & Reviews: Time for leadership and teams to evaluate strategy for the previous quarter and plan for the future quarter.
Monthly Reviews: Time for leadership and teams to evaluate the results of the strategy for the previous month.
To outline the timing for each of these, the Chief of Staff determines what touchpoints need to happen, when they need to happen based on dependencies, and what the deliverables are.
For example, the deliverables for annual planning are (1) the CEO’s vision (based on our equation and in whatever format the CEO “thinks” in, often a memo or deck), and (2) an annual financial plan (in the form of a budget and forecast). We need these two deliverables before we can start product planning for the year ahead (and subsequently outreach and G&A planning). To create a vision deliverable and financial plan, we need (1) to understand how our current strategy is going and (2) an analysis of the competitive landscape, both of which are work that goes into Quarterly Planning & Reviews, i.e. the Chief of Staff will schedule Annual Planning to take place just after Q3 Quarterly Planning & Reviews.
Then the Chief of Staff goes a layer deeper, identifying what work needs to go into Quarterly Planning and Reviews. Quarterly Reviews are an analysis of the previous quarter and should consist of a review of the business and operational metrics for each team (working on an input metric), and a competitive analysis for each high-level output metric (which teams are grouped by). They are coupled with Quarterly Plans which are forward-facing plans outlining the business and operational metric goals we intend to achieve the following quarter and how we’ll achieve them, incorporating our learnings from the previous quarter.
Then the Chief of Staff goes one layer deeper, identifying what work needs to go into Monthly Reviews. Monthly Reviews are an analysis of the previous month and should consist of a review of the business and operational metrics for each team (working on an input metric).
The Chief of Staff takes all these layers and compiles them into a program with dates for each (including complementary dates for product planning, outreach planning, and G&A planning). Then they create a format for each meeting and a template for each deliverable (QBR, MBR). Eventually, they distribute the program to the entire company, sharing the meeting formats and deliverable templates so everyone knows when these touchpoints are and how to prepare for them (ideally they do this in a way with posterity, like a wiki and various comms channels).
Once all the touchpoints have been programmed and meeting formats and deliverable templates have been shared, the Chief of Staff’s job administering the operating model is just getting started! Now they get into the guts of the strategy, tracking progress and supporting teams.
They start to track every input and output metric, internalizing how the company works and how every part of the company is connected in a way that nobody else can (this makes it so they can provide that high-quality level of executive support). They’re able to spot problems early, bring the right people together to solve them, and pollinate the organization with learnings and insights.
They use this unique understanding to help teams craft operating model deliverables before they go to the CEO and drive every operating model meeting, supporting teams in how they evaluate and communicate about their work. In meetings, they push people to have hard conversations and make decisions. And they follow up on action items and ensure decisions are implemented.
They also facilitate alignment by finding ways to regularly communicate about the strategy and how things are going. Think weekly update memos and regular All Hands meetings, so everyone at the company stays in lockstep.
If they do this well, they become the company’s Chief of Staff, not just the CEO’s Chief of Staff. The teams want their support as they execute, which gives the Chief of Staff an even greater understanding of the organization and what’s happening in real time.
And the final pillar of the CoS job - special projects. After a few cycles of mastering exec support and designing and implementing the operating model, the CoS should have things humming to the extent that they can spend some portion of their time on strategic projects on behalf of the CEO. What projects you give a CoS depends on their skillset. Some of the projects I’ve seen CEOs hand to a CoS:
Market research and competitive analysis
PMing a new product that doesn’t have an obvious owner or has too many obvious owners
Kicking off new functions like PMM, Communications, or Policy at a younger company
Taking on Executive Communications for the CEO
It really depends on the person in the role, but the point is, you now have someone who can take on big, meaty initiatives.
The role of a Chief of Staff can be fuzzy. But if you center it on the operating model and providing executive support, team support, and handling special projects, this person can have a meaningful positive impact on the organization. That is until someone creates an AI application that is omniscient and omnipotent and can provide this level of support and connective tissue. Until then, this is a really important role and this is how to approach it.