Issue 7: Chief of Staff Holiday Grab Bag
We're answering some top asked questions in this issue!
Welcome back, aspiring and current Chiefs of Staff!
First of all, I want to thank all 1️⃣ 5️⃣ 0️⃣ 0️⃣ ➕ of you who have subscribed to this newsletter! When I first started writing this newsletter 3 months ago, I had thought maybe a few people would want to read what I had to say, but our little community has crossed the thousand person threshold and I’m excited to see what the new year continues to bring.
If you’re interested in sporting a little swag to show that you’re a part of the Ask a Chief of Staff community, I’ve added two stickers to my “Extras” page so that you can rock a little Chief of Staff pride. As many of you know, I hope to always keep the content of this newsletter unpaid so that it can help as many people as possible so any donations you’re willing to throw my way helps me keep the content flowing and the domain name paid for (keep your eyes peeled for a formal Ask a Chief of Staff website coming soon in the new year!)
🤔 Some Frequently Asked Questions
In this week’s issue, I’ll be answering some of the many questions that our readers have submitted in the last few months. If you’re interested in submitting a question for a future issue, feel free to do so below!
How do you approach your first few weeks as a new Chief of Staff? What should you be thinking (or asking) about?
When it comes to your first few weeks in the role, the biggest thing you can do to set yourself up for success is to build trust: with both your CEO/Principal and other members of the executive team. Without a strong bond of trust, you won’t be able to truly execute on any impactful initiatives, strategic or tactical, and you might feel stuck running more “errand work” rather than being a true extension of your principal. I’ve actually written about your first 30 days on the job before in this article I wrote for Chief of Staff Network. If I could sum up the first few weeks of your role, I would emphasize:
Observe - Take stock of everything around you: how does your principal spend their time? What are the things the rest of the executive team are working on and where are they getting stuck? What else are you hearing from the rest of the org on the ground level?
Ask questions - Take the time to set up coffee chats with others in the org and gain a pulse of what is top of mind. Ask about reading material you should be engaging with. Ask questions about the product your company is working on.
Synthesize - Put together all the information and start to figure out what are some “quick win” initiatives you can pull together. See if there are any trends worth surfacing up to your principal or if the information you’ve gained is “back burner” for now.
Execute - Begin to execute on initiatives assigned by your principal but also think about other places in the org you can step in to alleviate road blocks for others.
Additional Reading on your first few weeks as a Chief of Staff:
Can I be a Chief of Staff in my first experience? If not, which first position should I aim for?
As a general rule of thumb, and my own personal opinion, I advise against taking a Chief of Staff role as your first career experience. It’s not to say you can’t be successful if you do so, but here are some of the reasons why I think you should wait till your 2nd or 3rd role before becoming a Chief of Staff:
You need to build self awareness in your own working style: I’ve written about “self awareness” being the most important trait a Chief of Staff can possess and knowing your own strengths and weaknesses when it comes to working style only comes with time. Giving yourself a role or two to work with different personalities and try out different work environments will only serve to give you a better understanding of what your ideal working culture and surroundings are, making you a more efficient and productive Chief of Staff.
You need to learn what operating rhythms look like: your first working experience will give you the opportunity to not only work on some functional skills, but it will give you insight into how a typical company is run. You’ll sit on All Hands, quarterly planning meetings, manager 1:1s etc. so that you can learn general business functions. A Chief of Staff role is going to expose you to a multitude of new things that you haven’t had exposure to before so lessening that information overload in prior roles will serve you well.
You need to understand what personalities you work well with: Do you work well with dominating personalities? Do you need someone who is more verbal in their communication or do you prefer written? You won’t get a true sense of what your principal preferences might be until you’ve worked with a few different managers and managerial styles.
A Chief of Staff role can be a transformational one - I often attribute being a Chief of Staff to being the largest pivotal moment in my career. If you want to set yourself up for success and get the most out of the role, having some foundational understandings of yourself will help you succeed and be the best partner to your principal as well.
I'm confidently in my Chief of Staff seat, but I still crave a group of CoS peers to kick around comparable challenges & mind-meld with. What do you recommend?
There are a few Chief of Staff communities out there that I’m aware of. Please note, the only two communities I have personal experience with are On Deck’s Chief of Staff fellowship (now under the Coho umbrella) and the Chief of Staff Network (though I participated over two years ago so I’m not as up to date on what the community looks like nowadays). Here’s a short list of what I know is out there:
Coho Chief of Staff (On Deck’s spin off company - I used to run the On Deck program but have since stepped away from community management of this community)
Chief of Staff Networking Group (I’m a part of this LinkedIn Group and it’s a great free resource to get started)
It’ll be up to you to figure out which of these communities work best for you. They come at different price points and each one has slightly different offerings.
My other suggestion is to do a LinkedIn search for Chiefs of Staff around you, if you’re looking for local folks. When I ran the Chief of Staff fellowship, I would always suggest that Chiefs of Staff look for three relationships:
Mentor - someone who is ahead of you in their career and can pass on the learnings and mistakes they’ve made. They can advise and share experiences with you to help you forge the path ahead.
Mentee - someone you can pass on your learnings to. The best way to learn is by teaching and I always say that the best people to learn how to be a Chief of Staff from are people who are in the role right now. Pay it forward and share your knowledge with the next generation’s Chiefs of Staff.
Peer - someone who is at a similar stage of company or career stage. This way you can compare and contrast responsibilities and projects to see if there are things that you’re missing at your current role or things that you want to be more involved with. As a Chief of Staff, you’re often an island of one but you don’t have to go it alone. Finding peers can help you think through challenges and obstacles that come with this role while offering you an outside, objective perspective.
If you’re interested in being connected to Chiefs of Staff who can play any of these roles for you, reply to this email and I can help out! I’m connected to hundreds of Chiefs of Staff at all company sizes, industries, and career lengths and would be happy to help connect you!
Is it possible to do this role remote?
Short Answer: yes. With the way that the world has changed in the last two years, remote work has proven that it is just as, if not more, effective than being in person. I truly believe that you can build a strong working relationship that’s filled with trust remotely. You just need to be able to establish the right working rhythm between you and your principal. If you’re not in an office together, how do you still gather all the information and thought processes your principal is experiencing?
One great example I’ve learned is from Priya Monga, Chief of Staff to the CEO at Instacart. Every day around 5-6 PM, Priya expects a phone call (yes, a phone call!) from her principal where they’ll both take a walk and debrief on the day. It’s a chance for the two of them to catch up after busy days and fill each other in on things that the other might have missed. Building in this phone call into the day could be the equivalent of a coffee walk or water cooler chat.
Naytri Sramek, Chief of Staff at GitHub, has said that she would ask folks around her org for 15 minute debriefs on things that were top of mind, both personal and work related. It was a way for her to build psychological safety with coworkers who weren’t at the leadership level and give her a better understanding of the general sentiments around the company.
There are a variety of ways to ensure that there are open lines of communication between you and your principal and it’s a matter of figuring out what works best. Some CEOs enjoy functioning in a highly async manner while others work best with recurring standing meetings. Also realize that building communication is a process that will change over time as your relationship with your principal grows. What you start with day 1 may not look the same as day 30 or even 60 or 90!
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!
Accrue Savings - Chief of Staff to the CEO
Industry: Consumer FinTech
$25M Series A, 28 people team
Location: New York
Preferred Qualifications:
Finance and Operations experience, specifically quantitative experience in the finance realm
1-2 years experience working at early stage startups
Background in consulting is helpful but not required
Categorynauts - Chief of Staff to Mark Organ (Author of Why You Need Two Chiefs in the Executive Office)
Industry: Leadership/Coaching
Location: Toronto, Canada
Preferred Qualifications:
5-7+ years of overall experience
Experience building slide decks, leading customer success, strong project management
Interest in career/CEO coaching
Additional Chief of Staff Related Reads:
How to be an Exceptional Chief of Staff: Advice for Scaling Impact at Startups
So, You Want To Be a Chief of Staff?
The Secrets of the Chief of Staff Role
Chief of Staff: A Force Multiplier
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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 Maria and Helen for supporting the last issue!