With the rise of the Chief of Staff role in the startup world, I get a lot of outreach from both founders who are looking to hire a Chief of Staff, as well as people who are interested in learning more about the career path.
Having experienced the value of the CoS/founder partnership, I’m a huge advocate for both founders and the generalist-CoS-types who can find great success and fulfillment through it. Here, I’ll share a little of my personal experience. Eventually, I may build out more comprehensive resources.
If there’s one theme you’ll see repeated again and again when people talk about this role, it’s how versatile it is. The shape of the role depends on what the Chief of Staff brings to the table, what kind of work the organization is doing, and where the principal most needs support.
I’ve personally known Chiefs of Staff who were formerly educators, engineers, executive assistants, human resources leaders, and a variety of other backgrounds. Naturally, each brings a different lens and set of strengths. That said, a Chief of Staff will typically handle some version of the following:
Keeping the principal focused on the highest priorities
Working with the principal to set and drive strategic plans
Serving as a trusted sounding board and thought partner to principal and broader leadership team
Translating vision into execution plans
Building and optimizing internal operations
Managing executive communications and information flow, internally and externally
Issue triage and decision support
Leading special projects
External relationship management
Shaping culture
Rolling up their sleeves to handle whatever is required to move the organization forward
It’s also worth noting that a CoS role can occasionally own functional leadership in smaller orgs. For example, I know many CoS who oversee company operations, HR, technology, and/or handle EA tasks. As the organization grows, it’s not recommended that a CoS owns functional leadership or any recurring/long term projects, as anything that a CoS owns long term will take time and focus away from being a strategic partner to the principal.
What is a Chief of Staff?
Why I love the Chief of Staff role (and why you might too)
Like most CoS, I didn’t intentionally choose this role. After dabbling in online community building, client services, human resources, and operational leadership, this is where I eventually landed as I moved toward the work that energized me.
Some people are jackhammers who thrive in specialist roles, and some are hummingbirds who need breadth, novelty, and opportunities to cross-pollinate. The CoS role is a role that blends both. It requires a wide generalist toolkit, yet functions as a specialty in its own right. The novelty and breadth aren’t for everyone, but for those wired this way, it can be an immense source of energy.
Having a counterpart who can toggle between relationship building, strategy, and deep-in-the-weeds implementation is a valuable asset for founder-like people who generate a huge volume of things that need to get managed across a lot of different domains. The CoS isn’t the doer of all of the things, but they get to use their generalist ability to figure out how to get things done.
This role is also a good fit for people who are deeply curious about all aspects of the business and like helping others move their goals forward. I’m always looking for ways to work upstream of as many issues and opportunities as possible, and the CoS role allows for that to a great extent.
Why you might not love the Chief of Staff role
As much as I love and advocate for the CoS role, I would be remiss to not mention the “dark side”. Just like any other role, the things that lend to some people loving the role are the same things that will make others miserable.
The biggest difference between this role and others I’ve held, is the breadth and volume of novel, urgent, complex, and consequential inputs that need to be constantly prioritized and managed. The goal is, of course, to put systems and structure in to place that keep the chaos to a minimum and proactively address potential issues. But, to a large degree, the purpose of the role is to be a problem filter and controller of chaos.
Even for an experienced operator, it can be exhausting. I’ve seen many super smart and capable people burn out because they either couldn’t or simply didn’t want to sustain that level of operational intensity over the long term.
The good news is that many aspects of the role get easier as the partnership deepens over time. This “flywheel effect” is why the most successful CoS–principal relationships often last many years, sometimes even decades. Some organizations choose to rotate through chiefs of staff every few years, but in my experience that approach sacrifices much of the real value of the role. A fresh perspective can be helpful, but you can achieve that through consultants, coaches, or other specialists without disrupting the core relationship. The longer and stronger the partnership, the more a chief of staff can serve as a true second brain and force multiplier.
That said, as the organization grows, the demands of the role grow too. The hours will be long and dictated by other people’s calendars, the work will consistently make you feel like you’re out of your depth, and the intensity will be ongoing indefinitely. And you have to really make peace with all of that to be successful in the role. This is why I believe it’s so important for a CoS to be aligned with the principle and their mission (more on that below).
I’ve found a lot of great ideas and support in CoS/COO communities and highly recommend all CoS belong to at least one active group, ideally before you take on your first role. You can also find a wealth of information on youtube.
Finding the Right Partnership
One of the most beautiful things about the role is that it never looks the same. It is a highly adaptive role shaped around the needs of the person it supports.
This is also why it’s notoriously difficult to find a good match. These roles and the people who fill them tend to be shaped in very unique ways. This is true of all people, but it’s more pronounced in these support-oriented roles where you really need to be on the same wavelength.
Whether you’re seeking a role as a CoS or you are a principal who is looking for a great person to support you, the most important thing you can do is take the time to really understand the alignment and nuances in values, skillset, needs, and personality.
If you are hiring a CoS: Make sure you’ve done the work to understand what you need, as specifically as possible. As I mentioned, candidates will run the gamut of experience and skills, and you have to know what you’re looking for in order to assess someone against that.
If you are a CoS looking for your next role: It’s very difficult, if not impossible, to be an outstanding CoS if you are not deeply inspired by the principal and mission of the company. It is that alignment that will carry you through the challenges you will inevitably face.
Assuming skills and values alignment, also ask yourself:
Would I want to be around this person? Every day?
Does this person seem like the kind of person I can respect and trust on the deepest level?
Do we communicate in a natural, unforced way? Does our energy flow easily?
Do they inspire me? Do I think I can learn from them?
In my own career, as well as when hiring others, my mantra is: if it’s not a clear “hell yes!” (on both sides) then it’s a NO.
On paper, someone might be great, but the “vibe” just isn’t there. Listen to that. Your body can tell you things that your brain cannot make sense of.
When I’ve ignored my intuition in the hiring process, I’ve usually regretted it. And, conversely, when I’ve listened to my gut, I have not generally had regrets. Also, keep in mind that you can train most skills, but you cannot train on values alignment and being a good personality-fit.
It is ultimately alignment (or the lack of it) that determines everything about how this relationship will work day to day, and whether the CoS becomes a force multiplier or a source of friction. Time spent sussing these things out in a hiring process is well worth it.
Kind Words from Others
Brands I’ve Worked With
