Issue 10: 5️⃣ Reasons Why You Should Become a Chief of Staff
And a few reasons why you shouldn't.
Welcome back, aspiring and current Chiefs of Staff!
We made it to issue 1️⃣ 0️⃣: I can’t believe we’re in the double digits! I’m so grateful to our burgeoning community of 2️⃣ 0️⃣ 0️⃣ 0️⃣ ➕ and a HUGE thank you to those of you who have supported this newsletter through buying me a matcha 🍵, generously paying for subscription, or attending a workshop 🙏🏼
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If you’re reading this newsletter, you’re probably already aware: the Chief of Staff role has risen in popularity and prominence. A search on LinkedIn alone shows over 28,000 Chief of Staff job postings - not to mention there are quite a few Chief of Staff adjacent roles that aren’t listed (ie Head of Operations, BizOps Lead, etc.). A job that’s a few days old has over 200 applicants!
It seems, now more than ever, people are being more and more intentional about pivoting into a Chief of Staff role and while I couldn’t be happier to see that the Chief of Staff title is showing up on more and more resumes, the first question I ask any aspiring Chief of Staff is “Why do you want to be a Chief of Staff now?”
While having a great answer to this question is important when you’re interviewing for the position, it’s just as important to evaluate your own motivations.
Why Would You Want to be a Chief of Staff?
✅ You’re a generalist at heart looking to advance your career.
This is by far the most common response and reason to want to become a Chief of Staff. My own experience is most closely tied to this. When I approached the 2 year mark during my time working in Operations at AngelList, I knew that I wanted to stay wide while leadership was telling me I had to pick a lane: Account Management or Recruiting. I enjoyed doing a little bit of account managing and a little bit of recruiting, but firmly positioning myself in either bucket felt wrong to me. It was then I discovered the Chief of Staff role and realized that there was a path forward to me to continue staying wide but getting to move closer to leadership.
Just as there are tracks for individual contributors or aspiring managers to move up in the ranks, there are now pathways for generalists to continuing growing upward: Chief of Staff being one of them.
✅ You like people wrangling.
This isn’t to be confused with being an extrovert. There’s a common misconception that being a “people person” means you have to be outgoing, effusively enthusiastic, and a social butterfly. Many of the most successful Chiefs of Staff I know are actually introverts, making their cross functional interactions that much more meaningful because they are more intentional and thought out.
A core skill that every Chief of Staff needs is the ability to build relationships and get team memberships in different functions to row together 🚣🏻 If you’re uninterested in the dotted lines hierarchies and influencing, but not managing, others, a Chief of Staff role might not be for you.
✅ You like figuring out how to get things done.
“Ambiguity” and “prioritization” are your middle names. Also add “resourcefulness,” “self managed,” and “executor” to that list. When I was a Chief of Staff, I would jokingly call myself the “Chief Google Officer.” There wasn’t any task that I wouldn’t take on and I found a way to get things done, whether it was executing on it myself or figuring out the right people to tap to make it happen. As a Chief of Staff, you’ll be given a long leash and an end goal. How you get there is wholly up to you and there’s often no right or wrong way (within the bounds of ethics 😅).
The other analogy I like making is that a Chief of Staff is often a “Ditto” around the office. Shoutout to all my millennial readers that remember this original 150 Pokemon. If you’re familiar with this slime looking creature, you’ll remember that it has the ability to take on the form of any other Pokemon, but it maintains its little dot like eyes. The point is, you’re going to take on a lot of functions that you may not be perfect at, but it’s going to be good enough. It’ll be good enough to get the job done and you probably shouldn’t be in the function long term, but it’s a suitable tide over until it makes sense for a specialized hire to step in.
✅ You’re comfortable leading from the shadows.
A Chief of Staff is the ultimate servant leader. There often very little “glory” in the role and you’re going to be subject to doing some unglamorous things. For me, that was accounting. Not in this life or the next will I ever be a CPA, but someone had to wrangle QuickBooks and if it wasn’t me, it would be the CEO and that just wasn’t the right area of focus for him.
When change management inevitably arises, you are often the first to model the changed behavior: whether it’s implementing a new software, executing a new communication style, etc., you’re often the one leading the charge while not having a direct management of any particular team or person. Learning how to influence without authority is a pillar of the Chief of Staff role.
✅ You’re looking to gain proximity to leadership.
If working alongside leadership excites you and you want to be in the room where it happens, being a Chief of Staff could be right for you. Whether it’s to be involved in the decision making process or you’re looking to learn more about leadership overall, this role will afford you both. Especially for folks who have aspirations to become a founder or C-Suite in the future, a Chief of Staff role is a perfect training ground to help you see how an early stage company is run and you’ll pick up a lot of hands on lessons along the way. Some folks even take a Chief of Staff role over attaining an MBA because it’s truly a crash course in running a business.
You shouldn’t become a Chief of Staff if:
🚫 You’re just in it for the title.
I hope this goes without saying but if you’re only interested in being a Chief of Staff “because it looks good on my resume,” that’s not a good enough reason.
🚫 You’re looking to specialize in a specific function.
If you’re looking to be a better marketer, sales leader, recruiter, [insert your choice of function here], the Chief of Staff role isn’t for you. You’ll likely gain experience in any of these functions, but you won’t focus on each one enough to truly gain the type of experience you want to build a further career in it.
The caveat to this is if you’re not sure what function you might want to specialize in - in which case a Chief of Staff role might give you some insight into which functions you enjoy and don’t.
🚫 You enjoy managing others and building a team that works for you.
Most Chiefs of Staff don’t directly manage anyone. If you’re looking to manage direct reports and be invested in their career growth, a Chief of Staff role likely isn’t the right fit. A Chief of Staff might sometimes manage an EA who sits in the office of the CEO, but indirect management tends to be the most common type of management a Chief of Staff will do. If anything, a Chief of Staff needs to be extremely well self managed and even better at managing upwards when the principals needs a firm hand and/or guidance.
🚫 You work best in highly structured environments where outcomes and expectations are clearly defined.
Say it with me “Chiefs of Staff thrive in ambiguity.” If you’re looking for a job where you’re given a to do list of things to accomplish, this role isn’t for you.
Have more questions about being a Chief of Staff? Submit them below and I’ll answer them in an upcoming issue!
Open Chief of Staff Roles:
I’ll be sharing a few of the roles that I’m working on each issue. If you’re interested in any of these positions, reply to this newsletter with a copy of your resume and I’ll follow up!
Pronto - Chief of Staff to CEO
Venture backed, pre-seed
Location: San Francisco (bonus points if you have a car!)
Preferred Qualifications:
✅ Early stage startup experience, 3-5+ years of overall career experience
✅ Strong sense of urgency and prioritization
✅ Ex-consultant
✅ Atypical backgrounds are great and encouraged! ex: ex-military folks looking to transition into tech/startups
Web3 Platforms - Chief of Staff to CEO
Venture backed, $4M Seed
Location: San Francisco/London/Taipei, travel required
Preferred Qualifications:
✅ Product management background, experience working with engineers
✅ Consumer product experience
✅ Early stage startup experience
✅ Experience at VCs or in fundraising
Additional Chief of Staff Related Reads:
Leidos Chief of Staff on Why a Successful Career Path Isn’t Always a Straight Line
The Chief of Staff role: being the ‘CEO’s right-hand’
The Psychology Behind Meeting Overload
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👋🏼 Until the next issue,
Clara
PS: I’m going to work hard to keep all the content in my newsletter free so that it’s accessible for everyone, but if you want to help support my writing endeavors, you can buy me a matcha 🍵 Special shoutouts to Amanda, Jennifer, Connie, Albi, Martin, and Adia for supporting the last issue!