This article is written by Sonja Manning, who is Chief of Staff at Levels.
My first exposure to a Chief of Staff was Leo McGarry on “The West Wing.” And while watching Leo navigate the political machinations of President Bartlet’s Oval Office was entertaining television, his day-to-day role was of little use to me in prepping for my own role as Chief of Staff at a tech startup.
Put simply, a Chief of Staff’s primary directive is to make a leader more effective — prioritizing precious time, optimizing workflows, and even driving strategic projects. But how this slightly fuzzy mission is executed can vary widely from company to company based on size, stage and industry — and even two Chiefs of Staff in the same org can have very different roles, depending on the needs of the executive they work closest with. And if your company also has executive assistants on board, there’s an added layer of confusion about how to differentiate the two distinct roles. In other words, part of the job of a Chief of Staff is figuring out the job itself.
I joined Levels as its first Chief of Staff, reporting to co-founder and Chief Medical Officer Dr. Casey Means. To set the scene, Levels is a Series A company focused on reversing the metabolic disease epidemic by empowering people to understand their health with biosensors and closed-loop feedback. Casey operates as the external face of the company in media (having been a guest on over 200 podcasts — for more on the Levels podcast strategy, check out this Review article) while also supporting several functions internally (including Editorial, Growth, Partnership and Product) and recruiting and managing the company’s advisory board. As Levels grew and Casey’s responsibilities and public-facing opportunities expanded, she decided to hire a Chief of Staff to help scale her time.
As I was onboarding to my first Chief of Staff role, I realized that there wasn’t a turn-by-turn roadmap for how to be exceptional at the job — so I crowdsourced guidance from folks in the startup community, leveraging Chief of Staff Networks such as Voray, OnDeck, a16z, and scouring LinkedIn for connections who would be willing to lend their hard-won expertise.
In this article, I unpack the best advice I received from 20 other Chiefs of Staff at early-stage tech companies. I’ll also thread that advice together with how I’ve tactically applied it in my own role as the first Chief of Staff at Levels — in which we work almost exclusively in a remote and asynchronous manner.
While the Chief of Staff role indeed varies considerably, I identified 10 key tips and guiding principles that can help any Chief of Staff (or someone with a particular interest in this unique startup role) achieve success as they get onboarded and hit the ground running. I’ve bucketed the following advice into key milestones for scaling your impact in the first month, three months and six months.
IN THE FIRST MONTH
Tip #1: Communicate async with the goal of building trust with your principal.
As Oliver Belanger, Chief of Staff at Merit, puts it: “The more trust you have, the more impact you can have.”
I truly can’t overstate how important building trust is (that’s why it’s the first tip on the list!). However, in my remote, mostly asynchronous role at Levels, the onramp to trust wasn’t quite straightforward. While Casey and I certainly had sync calls, particularly in the earliest days, Levels’ culture puts a strong emphasis on “async-first,” deep work and minimizing sync time. I needed to learn to build trust and communicate with Casey within that cultural framework.
Instead of sitting on countless Zoom meetings, we used async videos for “job shadowing.” Casey would record hours of passive async Loom videos of her conducting her work, like prepping for podcasts, responding to emails, writing content, or processing direct messages. By watching these at high speed, I was able to learn her workflows, note opportunities for systemization or efficiency, and see how she thinks and writes. These were crucial resources for me to refer back to again and again as I continued to take on more responsibilities.
I also sent Casey daily end-of-day Looms — this replaced the “hallway chats” or “quick brain dumps” and included ideas or actions that were top of mind, areas to align on, or any blockers. It also enabled us to share screens and provide additional visual context. One of the best parts of this process was the ability to absorb each other’s async videos at 1.5 or 2X speed, pause to comment or take notes, or listen again to understand something more deeply. Casey would comment on my Loom with any feedback or suggestions and would often send her own short Loom with any lengthier feedback or thoughts for the following day. With the ability to share your screen and walk through what you’ve just worked on, these async videos were a rapid accelerator of trust.
Even if your company doesn’t operate quite as asynchronously as Levels, think about how you can leverage async communication to accelerate your learning and trust in the early days — as your executive will likely not have countless hours of free time to spend on Zoom meetings or sitting side-by-side.
Tip #2: Take the time to get things right — not every hour needs to be productive.
When you join a startup, you’re excited to get in on the action and start adding value right away — that’s probably why you joined a fast-moving company in the first place. When I joined Levels as a brand-new Chief of Staff, I had the exact same mindset, and I was ready to race out of the gates by day 30.
However, I found my best work came from blocking deep work time on my calendar, setting a timer for two-plus hours and not looking at my phone, pings, email, or any company communications. This aligned with the advice I received from Clara Ma, Program Director at On Deck for the Chief of Staff fellowship and a former Chief of Staff at Hugging Face: “Give yourself time to do nothing but think and chew on a problem; not every hour needs to be productive.”
As Kevin Weiss, Chief of Staff at Reforge, advised: “The weeks when I’d carve out multiple hours to reflect on the industry and business, I’d be able to contribute in more strategic ways — but if you don’t really block that time it’s easy to experience death by 1,000 cuts. Lots of things can funnel to you as a chief of staff, so proactively making time to think about the highest leverage places to focus is critical.”
This deep work time was an aha moment for me, as I previously thought productivity meant being the best at whack-a-moling my notifications faster than anybody else and being instantly responsive at any time. But as Johann Hari states in “Stolen Focus,” “If you are interrupted, it takes you an average of 23 minutes to get back to the same level of focus you had before you were disturbed.”
Building sustainable systems and solving problems take deep work — carve out the time to do this work rather than trying to squeeze it in between responding to emails and executing your to-do list.
At about month four at Levels, I took the deep work one step further and took my first “think week,” which was originally inspired by Bill Gates. Every Levels team member, no matter level or function, is encouraged to take a week without meetings or deliverables, but instead to spend the time doing deeper work. During this think week, I was able to draft some memos to clarify my thinking, read a few of our advisor's books (and even write this article). The think week enabled me to create documents that accelerated the impact possible through this role.
If you’re not able to take a full think week, consider how you can create blocks of deeper work on your calendar so you can think bigger picture and reflect on your learnings thus far, not just play whack-a-mole with your notifications.
Tip #3: Define and communicate your vision for the role — and then prepare to be agile.
Some apt advice I got from Alex Priest (formerly of Wheel and Uber), was to “get crystal clear on the role as best as you can as early as you can.” When I joined Levels, Casey had created a CoS Onboarding document that outlined her history at the company, current priorities, and initial action items for me to focus on. As an example, a few of the initial priorities in this document included:
- Saving and scaling Casey’s time by creating systems for podcast and media prep.
- Growing Casey’s public presence as a metabolic health thought leader by effectively distributing Levels content across her channels.
- Managing the next phase of the Levels Advisory program to effectively engage and activate our Medical Advisors.
While this onboarding document helped create clarity, I soon learned the role will never feel set in stone.
Strategy is ultimately about choice, and in startups, there’s no shortage of trade-offs and strategic choices to be made.
At the end of my four weeks of onboarding, I wrote a Chief of Staff Initial Vision, Strategic Priorities & Initiatives memo about my vision for the role, strategic priorities, and proposed first initiatives (here is a template if you’d like to follow a similar structure). The document included:
- Background. The company information I synthesized to inform the role’s vision
- Vision. My north star for amplifying Casey’s impact in service of Levels
- Strategic priorities. After working with Casey for several months, I was able to start to provide my personal perspective on questions such as: What are unique things that only Casey can do? What is her zone of excellence? Then, what are the ways Casey’s zone of excellence can add unique value for Levels? Every executive at a startup is being pulled in many directions, and a Chief of Staff can help support ruthless prioritization for their principal based on company goals at that moment in time. The answers to those questions manifested in three initial priorities and each of the priorities had a specific goal with a time horizon.
- Initiatives. Each of the initiatives had a goal, description and expected output. This became an initiative tracker to make my work visible across the company.
- Next steps. The process for getting alignment on this document, and the initial action items.
- Team Thoughts. A place to memorialize team feedback and thoughts, so it’s easy to reference or reflect on later.
I had to learn to worry less about “getting it right” and more about “getting it moving.” Instead of waiting until the role was perfectly defined (I would have been waiting a long time), I started communicating iteratively with all stakeholders I worked with about my priorities and kept them updated as they shifted. Documentation leads to conversation, which leads to alignment and then the ability to execute. The areas outlined in my memo had significant overlap with Casey’s CoS Onboarding document — but not 100%.
Get comfortable communicating in-flight updates and processes versus waiting until something is finished. It’s a critical element of building trust and confidence, especially in an early-stage, remote and async company.
IN THE FIRST 3 MONTHS
Tip #4: Don't just book more meetings; instead, build more effective systems.
As an early-stage startup, Levels is growing quickly — and any gap in information sharing or knowledge management signaled to me that something was missing. Oftentimes, the first instinct for solving a problem or filling a knowledge gap is to schedule a meeting.
Instead, my recommendation is to lean towards building systems, rather than booking meetings.
For example, Levels works in varying capacities with a number of high-impact advisors, and my challenge was to figure out how to increase visibility across the team on how we engage with these trusted advisors. Without this visibility, certain functions at the company were missing out on their work. For instance, if an advisor is doing sponsored research with us, but the marketing and content teams aren’t aware, an opportunity is missed for the teams to promote the project and share it with the public.
But rather than book a monthly “advisors sync” on the calendar, I leaned on async systems. As a lightweight method to boost visibility across the team, I compiled information and sent out “Advisor Headlines” every 2-3 weeks. Now, I have created a semi-automated “Advisor Interactions Tracker,” managed by our executive assistants, that includes updates from various team members that are engaging with our advisors. Anyone on the team can see for themselves what the latest conversation or interaction was and gain full context.
That’s not to say that meetings aren’t valuable — but in my experience, they are best leveraged for building relationships and getting to know your colleagues, rather than for information-sharing.
Tip #5: Find productivity tactics that work for you, and be religious about using them.
In a widely-read Review piece, Levels CEO Sam Corcos recommends ditching the to-do list entirely and leveraging your calendar instead. But as an unabashed list lover, I knew this exact advice wouldn’t work best for my working style. However, in this role, I quickly ended up with a list of 50-plus items, and I felt like all the balls were back in the air again.
By contrast, Christian Keil, Chief of Staff at Astranis recommended: “Keep two lists at any given time. List one includes things you need to talk to the principal about the next time you catch up. And List two is your back burner list of things that need to happen without the principal’s involvement. Jodie Sweitzer, Chief of Staff at Everlaw writes down the top three most important things she has to get done first thing every morning — and declares the day a success if those things get done.
I considered all of these ideas and found that a combination of five systems with varying levels of detail works best for Casey and me. It sounds like a lot — but stick with me.
Here’s our approach:
- Individual to-do lists with the major items to accomplish each day, organized into categories: read, write, think — with estimated time to complete each task. This helps me set an achievable plan for the day and the week. At the end of every day, I go back through and jot down how long each thing actually took me to complete, which provides the opportunity for both an instant brief reflection, as well as enables me to have a macro time tracking system (which I’ll dive into a bit more below).
- A weekly and monthly priorities doc where we track Casey’s weekly top 3-5 priorities (the most high-impact projects we must move that week) and top five monthly priorities (the five overarching things that the weekly priorities should connect to). We review these on Monday morning and on Friday afternoon during an end-of-week sync. This, along with our calendars, becomes a retrospective for what was accomplished in a week. The best part? By Friday, we revisit this document and are always pleasantly surprised that we moved the big priorities.
- An ongoing discussion doc with a running list of items for us to discuss during our check-ins or through our async Looms that both Casey and I add to. Items get checked off after they are discussed or completed. This reduces so much cognitive burden because everything has a place and lives there until it is done.
- Calendar showing when the work will happen. As an aspirational, “Rome could be built in a day” type of person, tracking exactly when I will accomplish tasks on calendar blocks is essential in keeping me honest about what I can achieve in a workday. Often, if I’ve blocked a task for 60 minutes and after 60 minutes I’m not done, I’ll either ship the version I have or re-scope the task to get more honest with myself about what’s really needed to move this forward.
- Automated time tracker: Using my calendar and to-do list, I can honestly assess and reassess how I’m spending my time. Oftentimes the tasks that feel like they take the longest are put in perspective at the end of a month. These insights help tell me which work areas I truly find energizing, and which ones I should focus on systematizing and getting off my plate.
Tracking tasks on your calendar is a great forcing function for shipping work that’s less-than-perfect (because, when it comes to startups, perfect is the enemy of good).
Tip #6: Learn as much as you can about your principal — especially their superpowers.
“Find what your principal’s superpowers are and get clear on your own superpowers — then lean into them as much as you can,” suggests Melissa Quarto, Chief of Staff at Yield Guild Games.
Besides building a relationship (and friendship) with Casey, I focused on really understanding her superpowers and then designed systems, processes, and support around everything else so she can focus on those high-impact zones. I learned what skills I could elevate or supplement, as well as where my skills were a unique value add. Here are a few hypothetical ideas for amplifying your executive’s superpowers and offering support:
- If the principal has a key organizational initiative that they need to push forward but they don’t have the bandwidth, you can get their initial input via recorded conversations, Loom videos, and notes — and then you can take the lead on the special project with their guidance. Or try partial implementation, taking on the bulk of the work before sending it to the executive for their final flourish.
- If the principal takes on too much and has trouble saying no, you might be able to add value by helping to create a prioritization framework and then helping to ruthlessly defend time against it.
- If the principal is uniquely skilled at creative work, synthesis, and communication (but is less focused on documentation or process), you might be able to develop a system for capturing their thoughts and creativity-sharing across the team in a more effective way.
- If the principal is skilled at relationship-building but is less adept at follow-ups or digital communications, you could help develop a system for templating emails and engaging executive assistants to monitor inboxes.
Tip #7: Keep track of learnings, they compound quickly.
As I started working more closely with Casey, I kept a “Pearls of Learnings” doc, where I would compile feedback and insights that Casey shared with me or insights from my own self-assessments. This was based on advice from Jessica Fain (formerly of Slack): “The Chief of Staff role affords valuable visibility into executive conversations. I wish I had better leveraged those moments as longer-term learning opportunities for myself sooner — now I keep a journal of executive wisdom.”
Take time to memorialize your learnings — they occur often, but the lessons can be fleeting if you don’t document them.
Here are a few examples of lessons I’ve documented for myself during my time as Chief of Staff:
- Lesson 1: Connect the dots back to the larger purpose. In the CoS role, you can feel like you are doing 10 to 15 things a day ad-hoc. But because the nature of the role is cross-functional, those tasks are rarely ad-hoc, and most tasks are usually connected to org-wide objectives and purpose. One of my early learnings was that I have a responsibility to connect those dots between Chief of Staff tasks and higher-level strategies for others in every communication.
- Lesson 2: Less is more. It’s important to understand that often sharing more information is actually less powerful. It’s always a balance to determine the right level of context or detail to share. I have a sticky note on my desk that reads “Sonja, how can you cut that message by 50%?” to make my communications as crisp and concise as possible.
- Lesson 3: Try to be the culture bar-raisers. As an inherently cross-functional team member, and a representative of your executive, there is a huge opportunity to be a culture bar-raiser at the company. Invest the time in deeply understanding your company values and considering how to demonstrate them (and recognize others when they live the values).
IN THE FIRST 6 MONTHS
Tip #8: Build systems to make yourself obsolete.
You are the leverage for your principal, but you also need leverage. If I were to only take on tasks from Casey’s plate, I’d soon be underwater. I needed to let go of and unlearn the idea that a full — or overflowing — plate meant I was adding value.
True value means making room on both your executive’s plate and your own plate, while scaling your impact together.
Some examples of systems we needed, built, and then refined in the first six months:
- Managing communications: We created numerous systems, but leveraging executive assistants for communication has been critical. We’ve established systems for EAs to do call prep, create meeting notes, update snippets in Superhuman, and draft responses for everything from emails to LinkedIn messages.
- Sharing Levels content on Casey’s social channels: Given that Casey is involved in a large amount of the content that Levels creates, one of our first priorities was to distribute this content more effectively and grow the audience for Casey and Levels’ social media platforms. I am passionate about digital marketing, but I am not a digital marketer. Yet, as a systems builder, I was able to develop a system to take the content Casey is involved in and garner significantly more visibility on it, also resulting in audience growth. Specifically, Casey’s Instagram audience increased 68% in just over three months. We did this by establishing content, creative, copywriting, planning, and tracking systems that allowed us to publish a new post every day based on content Casey creates for Levels. This involved keeping our EAs in the loop, training them to use Figma and other tools, designing a semi-automated social media calendar and system, and outlining a clear process for all of the stakeholders involved. Prior to this, distributing Casey-involved content was ad-hoc, sparse, and inconsistent, limiting the company’s ability to position Levels and Casey as thought leaders in the metabolic health space and support our podcast partners by sharing digital assets. (For more on our biggest lessons here, you can check out this public memo.)
Ask yourself “Do I do this every day or week?” If the answer is yes, consider ways to systematize or offload those tasks. While you may think that being CoS is someone who gets a lot delegated to them, the truth is that YOU should be delegating masterfully for both yourself and on behalf of your principal.
Tip #9: Be a strategist in addition to being an executor
Chiefs of Staff are often very operations-focused. It’s easy to become the Chief of Executing Things, but the visibility inherent in the role means you are set up to operate strategically. For Casey and I, this means pausing and reflecting before saying yes to something. In fact, we made a framework for what must be true to get to a “yes,” such as asking ourselves questions like 1) Is this something only Casey can uniquely do? and 2) Will this activity contribute to the most important objectives for Levels in the next 6-9 months?
Since memo writing is so critical to how we make strategic decisions at Levels, I took the lead on writing a number of key strategy memos for work that Casey is involved in (e.g., a memo on “Systematizing Structured Insights” from our Levels data set, a memo on our “UK Advisory Relationship Expansion,” and creating a video series called “Levels Kitchen” to bring more cooking content to our members.)
While most of the memos I wrote are directly tied to Casey’s Areas of Responsibility (like content and advisory board management), I was also tapped to take on some strategy for the company outside of my direct work with Casey, including revamping the company-wide OKR process and 10x-ing our team’s delegation skills (as we work with a large team of Executive Assistants.) The balance of both creating and executing on strategies makes the role feel energizing and sustainable.
For all my systems building and strategic work, sometimes I still execute on assistant-level tasks, which is inherent for any person at a startup. As Martha Beck famously says, “How you do anything is how you do everything.” This means if a belt is missing during a photoshoot, I’m going on a quick mission to find the best belt nearby. No job is too big or too small. With that said, a key part of the role is systems building, so it’s your responsibility to create systems so that you aren’t stuck doing minor tasks for a large percentage of your time.
Tip #10: Make time in person to step away from the work and just connect
One reason why I love my role as the Chief of Staff at Levels is because I feel like every day I’m solving one of the most important and existential problems with a friend whom I deeply respect. While 90% of my relationship with Casey has been built async, the sync time together has improved our trust barometer and helped us gain a deeper appreciation for one another.
For example, when Casey was in LA for a series of podcasts, we took a day off to hike, eat healthy meals we both enjoyed, and spend quality time together. Over the last 6 months, we’ve plunged in glacier lakes, got our sweat on at Barry’s classes, hiked in the Santa Monica mountains, and biked all around NYC on Citi Bikes.
To get to know each other more personally early on, Casey and I liked to start off any sync conversation we had with a School of Life question (a prompt for a personal share.)
Learning as much as I could about Casey helped me gain empathy and understanding of how she thinks, works, feels, and operates. I tried to put myself in her shoes as much as I could.
You don’t need to be best friends with your executive, but you are never too busy to prioritize building relationships and building additional trust.
WRAPPING UP: FOCUS ON THE HOW, NOT THE WHAT.
The best part of the CoS role is it always evolves, especially as the principal and company evolve. As soon as I feel like I’m really getting good at something, I either hand it off, build myself out of it, or find that it’s time to focus on something else.
No matter how nimble and agile you are, change is always challenging. Human beings are hard-wired to resist change. Constantly changing roles, responsibilities and wearing new hats is taxing. However, I’ve found that keeping my mindset focused on how I work versus what I am working on enables me to cope with and embrace constant change.
Stay focused on how you scale time and impact. What you work on like will change, but the skills and approach for how you do it will stay the same.
My top five takeaways for how to be a good Chief of Staff include:
- Build and earn trust.
- Learn workflows and then design process-driven systems.
- Pause, strategize, then execute.
- Understand and enable your principals’ superpowers.
- Don’t ask how to help, just help.
How will you know if you nailed those five things? You’ve nailed it if you are not doing the same things you were three months ago.
A big thank you to the many Chiefs of Staff who spent their precious time chatting with me to share advice that informed how I execute this role at Levels, including: Alex Priest (formerly Wheel and Uber), Allison Winstel (mHub), Alyse Tognotti (Cresta), Bryn Loeffler (Turquoise Health), Caroline Casey (Relativity), Caroline Friedman (a16z, Kraken), Christian Keil (Astranis), Clara Ma (Ask A Chief of Staff), Ellen Napoli (Coinbase), Jen Gradone (Dropbox), Jeremy Kurtz (OfferUp), Jessica Fain (formerly Slack), Jessica Li (Beacons), Jodie Sweitzer (Everlaw), Kevin Weiss (Reforge), Louis Bi (Supermove), Melissa Quarto (Yield Guild Games), Oliver Belanger (Merits), Rebecca Nounou (Sweetgreen), Troy Straub (Terminal).