Issue 2: What skills do I need to become a Chief of Staff?
And how can I build those skills in my current role?
Welcome back to issue 2!
Thanks for coming back and if you’re new here, consider subscribing to get the latest issue in your inbox! In this week’s issue, we’re going to chat about the skills you need to pay the bills become a Chief of Staff.
The questions I usually get from first time/aspiring Chiefs of Staff usually go like this:
“What skills do I need to become a Chief of Staff?”
“Should I go back to school and get my MBA?”
“Can I be a Chief of Staff if I’m not a former management consultant?”
The short answer to those two latter questions is “NO!” I’m not a former management consultant, nor do I have an MBA (though my mom is constantly asking if I want to go back to school 😅 ). The first question is going to take a little more writing ⬇️
And if you have other questions you’d like to have answered about the Chief of Staff role…
What skills are necessary to become a Chief of Staff?
A common problem that I see many aspiring Chiefs of Staff run into is how to translate their current skill sets and roles into something that will fit a Chief of Staff mold. Oftentimes, Chief of Staff candidates are already doing some of the work that a Chief of Staff does, hence why they might be attracted to the role. But quantifying and explicitly acknowledging these skills can be a challenge.
Below are 5️⃣ skill sets that you can build in your current roles and highlight in resumes when applying for Chief of Staff roles.
PS: If you’re an aspiring Chief of Staff that wants help with updating your resume, reply to this email and I can help you out!
📣 I want to give a special shoutout to Philip Burns and Pradeep Kanagaraj who commented on my original post (4️⃣ Characteristics of a Chief of Staff) and helped me think through more skills that Chiefs of Staff need.
1️⃣ Self awareness
When I ran a pilot of the Chief of Staff Academy, the first week was focused solely on “Knowing Thyself.” I cannot think of a single more important trait than being self-aware when it comes to being a Chief of Staff. To me, having a high level of self awareness means:
understanding where your own weaknesses and shortcomings
knowing what you are capable of and where you can lead
When I was a part of Scott Amenta’s Chief of Staff Network, a resource that was shared was this Insight Quiz that can help you determine your level of self awareness. If you have ~15 minutes and a friend who can help you out, I highly recommend taking the quiz to know which of the quadrants you fall into:
💡 In your current role, don’t be shy about asking for feedback. The best way to understand what your perceived strengths and weaknesses are is to ask. I say “perceived” because perception can be misconstrued as reality and you can only work to change perception if you’re aware.
2️⃣ Cross functional collaboration
Another highly valued skill of a Chief of Staff is being able to work across departments to get things over the finish line. As a Chief of Staff, you might not sit in any particular department (similar to a CEO, you’re a part of every department). As a result, you’ll need to learn to gain alignment and work cross-functionally in order to get big projects started and completed.
When I worked in operations at AngelList, we were often the stand-in Customer Success team. Because I was talking to so many clients each week, I was able to go to our engineers and suggest workflow changes that would make the product easier for hiring managers to use. Not only was I able to help improve our product, I was also able to list cross functional collaboration on my resume and show that I could connect the dots between functions to help drive to a larger success across multiple teams.
💡In your current role, volunteer for opportunities that will give you insight into how other departments function. Ask department heads if it would be valuable to have your role’s insight in any ongoing projects. If you’re in Sales, would is be helpful to let Marketing know what potential clients are pushing back on in copy or brand? If you’re in Customer Success, can you share any insights you might have around customer interactions that could be built into the product with Engineering? More examples of cross functional projects here.
3️⃣ Ability to build trust
The ability to build trust is a necessity in the Chief of Staff role. The obvious relationship a Chief of Staff needs trust in is with their principal. By nature of where the Chief of Staff sits, you’ll have unfettered access to the company as a whole. This can include things like payroll information, company plans to up/downsize, potential funding rounds, investor/board contact information etc. Discretion is an inherent quality necessary in the role.
In addition to the trust you need to garner with your principal, you’ll also need to gain the trust of other C-suite members as well as the managers and individual contributors at your organization. These are the trust relationships that I feel like are often overlooked when people want to step into a Chief of Staff role. While much of the role is about pushing forward on the vision and mission of the organization, the people who can help you get things done are often the individual contributors who are heads down building product. Building trust with people who don’t sit at the leadership level will empower you with resources to take those strategic initiatives over the line. Additionally, it gives you even more visibility into the pulse of the org to know how people really feel instead of the “company wide pulse checks” where folks report on the progress of their projects instead of their thoughts on the company culture.
💡In your current role, get your colleague to tell you all of their deepest, darkest secrets. Just kidding! But do practice building genuine relationships. Ask about weekends, families, pets, hobbies, but don’t be pushy. Some people might not be comfortable sharing from the get go and you can learn to build psychological safety by leading by example and sharing your personal anecdotes and experiences.
4️⃣ Being T-Shaped
Chiefs of Staff go wide, not deep. The breadth of knowledge you possess gives you the creativity to solve problems differently. It's also why you’ll be able to work across so many departments and projects without having a degree in every single department.
In David Epstein’s book Range: Why Generalists Triumph in a Specialized World, he showcases several examples to make the argument that it’s often general, broad knowledge, and not specificities, that help people come up with creative solutions to problems. It’s the ability to cross reference different subject areas alongside work problems that give generalists and Chiefs of Staff the ability to see things from a bird’s eye view while navigating in the weeds to make things happen.
💡In your current role, ask questions about departments you’re not in. Get to know people working on projects you have no input or agenda in to understand how their roles play into the bigger picture of the company. As you gather these different puzzle pieces, you’ll be able to see the big picture. And just as you don’t need every piece of the puzzle in order to see the final outcome, filling in the different sections of sky, lake, and trees will give you the ability to getting a bigger understanding of how everything fits together.
5️⃣ Excellent communication
Communication is important in just about any role you’re in, but especially in this hybrid world and in a Chief of Staff position, communication can make or break the entire operating rhythm of a company. The keys to excellent communication are:
being concise
being contextual
being constructive
Chiefs of Staff are often called upon to communicate company wide changes, operating rhythm updates, annual planning and strategy, just to name a few instances.
💡In your current role, volunteer for opportunities to present information team or company wide. Maybe your team has just taken a huge project across the finish line. Volunteer to be the one to present the accomplishments to the rest of the company and ask for feedback on how the presentation went. You can even come up with a weekly update cadence on behalf of your current team. Anne Warren, former Chief of Staff at Lyft, suggests this “3Ps template” to share overviews and updates:
Why 3Ps? Providing consistent team progress updates is critical to keeping teams informed and aligned to move the business forward. These updates need to have more signal, less noise, and be more effectively cascaded up, down, and across teams. 3Ps is a framework for cascaded progress updates that keep the most relevant stakeholders at every level quickly informed across the company
What are the 3Ps?
Progress: Highlights, milestones, decisions, or reviews in the prior period.
Plans: Priorities and goals in the coming period.
Problems: Blockers, issues or flags.
What makes a good 3P?
Concise: Limit 5 bullets per section, and 3 lines per bullet. Use bold headers to help readers scan for relevance.
Contextual: Provide sufficient context for the target audience. Avoid acronyms and code-words. Clarify impact.
Clickable: Include links to launch tracker, docs (eg review decks), or dashboards with more detail.
Customer-focused: Focus on customer impact; include anecdotes or user stories in addition to metrics.
Constructive Problems: Include the next steps or actions in progress to address any problems, where possible.
Template
3P - {Team/Area} - mm/dd/yy
{name of author}
Progress
xx
xx
Plans
xx
xx
Problems
xx
xx
While the Chief of Staff role might have a new-looking job description, there are many qualities and skills that you’re already doing in your current role. With a bit of initiative and tenacity, you can position yourself for a Chief of Staff role and build your skill set for a future position. Don’t hesitate to reach out if you want to brainstorm ideas on how to make that happen!
Additional Chief of Staff Related Reads:
How to be an effective early stage employee. Hint: be helpful.
Scaling Startups Through Strategy & Operations
Becoming a Changemaker - Alex Budak
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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 Mary, Tom, Jeremey, Jana, Naida, Polly, Adam, David, Heather and Holly for supporting my first issue! And thank you to Cady for helping me edit this issue 😘