How to design a Chief of Staff role.
Once we design our operating model, we need someone to administer it - to be responsible for crafting each touchpoint and supporting teams on every deliverable. Administering the operating model is the foundation of the Chief of Staff role. Chief of Staff has evolved to mean a lot of different things across the technology industry - gatekeeper, project manager, air traffic controller, connective tissue, advisor, assistant, shadow CEO - a great Chief of Staff can fulfill these functions but they serve the company best when the role is centered on the company’s operating model.
The first thing a Chief of Staff does is program the operating model so it’s predictable and manageable. They create an annual calendar for the year ahead, outlining the touchpoints in the operating model, for leadership and teams to plan, execute, and regularly review our strategy at a cadence that allows the strategy to materialize (as outlined in my last post). It generally includes:
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 strategy for the previous month.
To outline the timing for each of these, the Chief of Staff determines what meetings 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 document 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. So the Chief of Staff will schedule Annual Planning meetings to take place just after Q3 Quarterly Planning & Reviews.
Then the Chief of Staff goes a layer deeper, identifying the work and meetings for 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 the work and meetings for 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 of meetings and compiles them into a calendar 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 distributing the calendar to the entire company, sharing the meeting formats and deliverable templates so everyone knows when these touchpoints are and how to prepare for them.
CEO Time Design
Once we have our annual calendar, the Chief of Staff turns their attention to all the things that have to happen between our annual calendar touchpoints by developing a “time design” for the CEO and, indirectly, for the leadership team and the rest of the organization. A “time design” is a thoughtful and well-crafted schedule. The foundation for a CEO’s time design are the touchpoints in our annual calendar plus touchpoints that have to happen between them. For example, a CEO will have regular product reviews to drive progress on the product roadmaps (the results of which are reviewed in our Monthly & Quarterly touchpoints). Those touchpoints must be scheduled and the formats and deliverables for those meetings must be outlined. Teams use the CEO’s time design to create team time designs, scheduling work and meetings to ensure the touchpoints with the CEO are productive, and the time design cascades. More on crafting a CEO’s time design in my next post.
Get Into the Guts
Once all the touchpoints are scheduled, and meeting formats and deliverable templates 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 day-over-day or week-over-week (depending on the company’s stage), internalizing how the company works and how every part of the company is connected in a way that nobody else can. 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’re evaluating and communicating about their work. In meetings, they push people to have hard conversations and make decisions, and they followup on action items and ensure decisions are implemented.
They also facilitate alignment through regular communications that complement the operating model, via company-wide memos, All Hands meetings, and board and investor reports, so everyone at the company stays in lockstep.
A great Chief of Staff has sufficient mind-meld with a CEO to administer the operating model the way the CEO would. This mind-meld only comes with adequate access to information. The best Chiefs of Staff have total access. They spend time with the CEO each day prepping for the day ahead and retro-ing the day previous. They attend every meeting the CEO attends, taking notes, distributing information throughout the teams, following up on action items. They read every email. They’re on every phone call.
This level of access ensures the Chief of Staff can administer the operating model effectively. It also benefits the CEO because it gives them a second brain. They can remain focused on the highest-level objectives while still having visibility into the details. They can keep that real-time pulse of the organization and the problems teams are facing. They have someone they can embed on teams facing challenges, confident that the right decisions will be made and they’ll be pulled in at the right time. And, finally, they have an effective soundboard, someone to whiteboard problems and brainstorm new innovations with. A CEO cannot have a second brain without giving that brain access to all the information that the first brain has (an added benefit: now you have someone to draft 90% of your email correspondence!).
Who to Hire
The Chief of Staff role requires a mature individual with high EQ and IQ who has adequate experience. There’s a trend in Silicon Valley of hiring a Chief of Staff straight out of business school. This is a mistake. A great Chief of Staff has enough professional maturity and operational and technical judgement to be the support system for teams and an effective problem-solver and partner to leadership. Maturity and judgement come from experience. The kind of experience doesn’t matter as much as breadth of experience - someone who has been in lots of different rooms, seen a variety of decisions made and their results.
Hire someone without an agenda. A Chief of Staff with something to prove or an axe to grind is toxic for an organization. Hire someone who cares deeply for the mission, loves operations, and wholeheartedly believes in leadership.
And finally, hire someone who thinks in a way that is complementary to how the CEO thinks. Note, this does not mean thinks the same way that the CEO thinks. CEOs should hire teams that help them play out the tensions they have in their thinking. The Chief of Staff role is no different. If you lean inflexible dictator, hire someone who demonstrates service leadership. If you lean analytical, hire someone who demonstrates bias towards action. If you lean fast and messy, hire someone who demonstrates meticulous precision. You get the gist.
If you hire the right person, center the Chief of Staff role on the operating model, and empower them with access to information to administer the model, they become the company’s Chief of Staff, not just the CEO’s Chief of Staff. The teams are supported and connected, the details are paid proper attention, and the strategy remains front and center.