If you’re a chief of staff, your core directive is to make your principal more effective. The specifics of the role can look very different from organization to organization and person to person, but what’s true across all versions is that your primary output isn’t your own work; it’s your principal’s. Their time is scarce and important, which means helping them narrow their focus, and then taking care of all other important work. Do that well and the whole team benefits.
At Coefficient Giving, we have a lot of Chiefs of Staff (as of writing this, we have 10!). Someone less familiar with our work might think that’s a lot, but it’s actually the right number for us for two reasons. First, Coefficient is organized as a set of relatively autonomous teams, so each team lead often ends up carrying the same range of decisions as a CEO (strategy, hiring, etc.), just at a smaller scale. Second, we’re growing really fast. Chiefs of staff can help on both counts.
I’ve been at Coefficient Giving for about eight years, a year and a half of which I spent as chief of staff to Derek Hopf, our Chief Operating Officer. This post attempts to answer the question: Once you’re made a chief of staff, what makes you good at it? In my experience, it comes down to supporting your principal in three ways:
- Protect their time
- Make information gathering cheap
- Architect how the work gets done
Protect their time
“Protect their time”…what does that mean? Beyond the obvious things (e.g. taking meetings on their behalf, guarding their calendar, prepping them for calls), I recommend focusing on the following two questions:
- Does your principal have enough time to think? And are they thinking on the right time horizons? Strategy, team structure, big investments, key hires — these are the kinds of things that operate on 1–2 year timelines and bring real returns to your principal and the organization. If their week is entirely reactive, something’s off and it’s on you to fix it.
- Are they working at the right altitude? That is, are they working on things that only they can do? Everything else should be delegated, handed to you, or hired for.
Below are a few strategies to ensure the above:
- Audit how your principal spends their time. Derek and I did this by analyzing time-tracking data: how much time he spent on meetings, how much on reactive work, and how much on longer-horizon work. As a result of that audit, we agreed on a set of tasks I’d begin owning on his behalf.
- Become a trusted stand-in. Things will inevitably come up that are negative leverage for your principal — that is, a shiny opportunity that pulls them from higher-upside work there. In such cases, you want to be the person they can sub in, so that the shiny opportunity is still captured without critical work going neglected. You’ll know it’s happening when you start getting looped into Slack conversations that used to be theirs alone. Advocate for that: Ask your principal to loop you in by default, then communicate clearly what you’re going to do next and when you’ll loop back.
- Own the ongoing processes that keep your team on the same page. For me, that meant running our annual planning and quarterly goal-setting process: setting the cadence, gathering inputs, maintaining the structure, and so on. The decision-making and team alignment that come out of planning are high-leverage work for your principal, but administering the process usually isn’t.
- You’ll sometimes have to advocate — even argue — that your principal should stop doing something. It might be uncomfortable, but it’s also an early indicator that you’re doing your job well. If you’re never telling your principal to drop work, you’re probably not protecting their time.
Finally, there’s a reactive version of protecting time too. Leaders get pulled into urgent, high-stakes projects; it’s the nature of the job. When that happens, it’s on you to help them complete it quickly and effectively, even if that means dropping what you were doing.
One heuristic I leaned on: Your principal’s problems are your problems. Don’t just mindlessly complete assigned tasks. Spend some of your own time processing whatever they’re processing, then reconvene and gameplan together. Over time, this builds a kind of mind meld, and the mind meld makes everything else in the role easier.
Make information gathering cheap
I often come back to Andy Grove’s High Output Management and his case for information gathering, which he calls “the basis of all other managerial work.” Every decision your principal makes is only as good as their picture of the facts, so building that picture is where a huge share of their time has to go. A good chief of staff makes that gathering cheaper and better.
I found two ways to do that:
- Build systems that extract information automatically. Our version of this was “snippets.” We asked each Operations team lead to write a short weekly memo sharing wins, problems, people updates, and priorities for the coming week, and deliberately instituted constraints — a standard format and a word limit — to force precision. Every Friday, Derek and I would read them and determine what we should focus on the following week.
- Talk is actually cheap (for you). It’s important to see yourself as a conduit for your principal. Talk to their people: direct reports, skip reports, potential hires and contractors, partners and stakeholders who matter to outcomes. Conversations are usually the richest source of information, and also the most expensive for someone short on time — so incur the cost yourself. You’ll surface useful intel, support coordination, go deep on active problems and opportunities, and, most importantly, make people feel heard. (Word of caution: Don’t go crazy. Start with one or two conversations a week and be deliberate about who you talk to.)
Architect how the work gets done
The third strategy is to improve the operating system underneath your principal. Your principal probably manages a lot of people across wide-ranging functions. That span can create drift and lead to incongruities. For example, there may be different methods of presenting decisions, structuring proposals, and reporting results across different audiences. That inconsistency has a real cost.
As a chief of staff, you’re one of the few people with visibility across several teams, which means you are uniquely well-positioned to spot when there’s confusion about how things should be done, and to help implement clearer and more efficient methods. The planning process I mentioned above is my best example: What started as recurring tasks I took off my principal’s plate became a shared goal-setting/commitment structure mirrored across every Operations vertical at CG, which made work across teams easier to align, compare, and improve.
Tips where your mileage may vary
The information above likely generalizes to any chief of staff role. Below are a few tips that served me well, but your mileage may vary!
- It’s normal to feel like you’re stumbling upwards. The role is highly reactive, and you often won’t fully know what the correct next step is. Ask for feedback often, and keep returning to the question of how you can make your principal more effective.
- Your 1:1s will be oriented around your principal, not you. In most 1:1s, managers ask their report how they can help. Yours will mostly be the reverse — you’ll be asking how you can help them. That’s the right dynamic, but it means you have to be deliberate about making room for your own development, whether in those conversations or elsewhere.
- Treat time with your principal like band practice. Trust is the foundation of your role, and it comes from spending a lot of time together — riffing, gelling, being generative. In practice, that means meeting a minimum of twice a week, and often more than that. Some weeks it’ll feel like you don’t need to meet. Meet anyway. Those are the sessions where you’ll end up riffing the most: organizing their thoughts, refining work products, strategizing around whatever reactive priority just sprang up. Reps compound into improved calibration: You learn how your principal breaks down problems, which trade-offs they weigh, how they communicate decisions, and so forth. A few Coefficient Chiefs of Staff describe the destination as becoming your principal’s second brain, so attuned to how they think that you can stand in for them live. Band practice helps a lot!
- Write a “working with me” doc (here’s a template of my own version that you can copy). Your role will be a mystery to a lot of folks. Outline what you do, how you work with your principal, and, most critically, how people besides your principal can leverage you. Once I shared mine, teammates started reaching out to chat about work and professional development. That forged new relationships, surfaced important themes across our people, and fed my information gathering. Inviting interaction is also a partial fix to the reality that being a chief of staff can be lonely at times, since you won’t necessarily have teammates outside your principal.
- Be an active listener, and create space for people to be candid with you. You’re a resource for your principal’s people, not just your principal. Be upfront that you want to hear about what could be going better. My favorite question to surface honest takes: “If you were the leader of X tomorrow, what would you do? Why aren’t we doing it today?”