Issue 5: Nailing Your Chief of Staff Interview
You've applied and now you have an interview! How do you set yourself up for success?
Welcome back, aspiring and current Chiefs of Staff!
👀 ICYMI, we’re hosting our very first Ask a Chief of Staff workshop and we’re going to be focused on how to improve your all company gatherings, specifically your all hands and offsites. Leading this workshop is Founder and Lead Consultant at The Gathering Effect, Lindsey Caplan. Lindsey will be leading a presentation and discussion on how to increase engagement at company events. This will be a limited capacity event (with the recording shared with all who register) so make sure you register ahead of time!
How Can I Best Prepare for my Chief of Staff Interview?
So you’ve submitted your application and a company is interested in chatting with about their Chief of Staff role. What can you do to best prepare? In this week’s issue, we’re highlighting the prep work you should do prior to your interviews. We’ll be breaking down the interview process into the typical stages we’ve seen, but keep in mind, the interview will vary from company to company.
📣 Huge shoutouts to Shaina Anderson for helping me with the content of this newsletter!
1️⃣ Intro Call
Do your research! As much as you can, look up the company and CEO/principal you’ll be interviewing with. Ensure that you know the mission of the company, the problem they are looking to solve, and at least a general sense of how they’re doing it. Look at the backgrounds of the execs/key leaders - where they came from, what roles they’ve held, their interests. Your goal is to go into any interview displaying that you’re informed and intellectually curious.
Prep your “Why?” When it comes to interviewing for a Chief of Staff role, be prepared to answer two key questions: 1) Why do you want to be a Chief of Staff? and more specifically, 2) Why do you want to be a Chief of Staff at [COMPANY XYZ]? When former Chief of Staff, Shaina Anderson, interviews Chief of Staff candidates, she’s looking for clarity and conciseness in these first two answers. She wants to know how a candidate “connects the dots” of their career and how they came to realize that a Chief of Staff role is right for them. You don’t want to bore your interviewer with every single item on your resume, they already have a copy of that to read. Instead, fill in the gaps where it might not be as obvious and have the narrative of your Chief of Staff journey well rehearsed and practiced. Think of your “Why?” as a movie trailer - you want to give them a preview of who you are, but leave them places to be able to ask questions and dig deeper into your background where relevant.
Here’s my 5 sentence pitch on myself as an example:
I grew up in the original Silicon Valley where my dad was a chip design and software engineer so I’ve always had a fascination with technology and startups. In my first role out of school, I recruited software engineers for startups in for the original D2C brands like Warby Parker, Dollar Shave Club, Bonobos, etc. That made me realize my interest and desire to go work at a startup and create the impact that I felt like I was missing from my recruiting job. Since then, I’ve worked at a variety of different startups from as small as 4 full time employees, to a Series D company (AngelList), always being a gap filler of sorts - jumping in to spearhead special projects, finding creative solutions to certain problems, and working as a bridge between different teams to drive towards a unified goal. Most recently, I’ve been looking to “level up” my skills as a generalist because I have aspirations of starting a company someday and really want to learn how to build a company from the ground up and have that 10,000 foot view of the org while also operationally learning how it gets done.
Prepare situations/anecdotes for the “preferred qualifications” of the job description. Review the job description and be ready to share examples of when you put these skills into practice.
For example: A natural aptitude for building strong, trusting partnerships across the organization.
Think about a time where you led a cross functional initiative at your current or previous company. Again, be able to distill this down to a short and pithy explanation. If you haven’t done something that is directly related, you can reference a time where you were part of a team that did this and talk about your own impact on the project. How did you communicate your progress? What might you do differently if you had been the one to spearhead the charge? What did you learn from the experience?
Questions to ask at this stage:
Why is [COMPANY XYZ] hiring a Chief of Staff now?
Using this leveling framework, are you able to glean what the top priorities of a Chief of Staff hire would be? Does that fit within the scope of work you’re looking for in your next role?
Has this principal had a Chief of Staff before? If so, what has that person gone on to do?
What are next steps in the interview process and when can you expect to hear back?
2️⃣ Take Home
Many Chief of Staff interview processes will include a take home. This can be anything from a case study to an analysis of data to a presentation on a project you’ve led before.
Reply to the take home email. Acknowledge receipt and also give a suggested deadline if one isn’t already assigned to you. That way, you can keep yourself accountable to meet a deadline, show that you are able to self manage, and also keep your candidacy top of mind to the company.
Don’t take more than the "suggested time.” While it may be tempting to go above and beyond and create a themed deck for your take home, keep in mind that this take home is meant to showcase what you’re capable of, but is still hypothetical in nature. Take homes are often more focused on the content, not the form. If you’re keen, you can add an additional addendum to your take home to state what you would do next if you were to take more time on the take home. For example: “The next steps of my analysis would be to…", “If I were to spend an additional hour on this case study, I would...”
Give yourself enough time to ask questions. Interviewing for a new role can often feel like a full time job on top of your current one, but this is not an assignment you want to speed through or leave to the last minute. I often suggest reading through the take home as soon as you get, even if you don’t start putting thoughts on paper yet. That way, you brain can start to work through some of the problems in your subconscious and you’re not starting from scratch when you do sit down to tackle it. Also, if there are any immediate questions that crop up in that first reading, you can reply to the interviewer and ask them before getting started.
Use an operating framework and rhythm of business that is appropriate for the size of company you are interviewing with. It’s important that you understand what is within the resourcing of a company and what is outside it’s scope. Don’t use a RACI framework if the company is at a seed stage and roles aren’t as clearly defined just yet. At the same time, if you’re interviewing with a later stage company, think about how you might present a solution like this internally and how might you template out communications to make sure all departments receive the information.
Be ready to present your solution. While it’s not always a requirement of a take home, you should still be prepared to talk through your solution in the next round of interviews. Make sure you can easily converse through why you got to the outcome you did, if there were any assumptions you made along the way, and be ready to answer questions about your take home as well. It might be helpful to have a friend listen through your explanation once and give you some feedback on what can be made clearer or less nuanced.
Questions to ask at this stage:
Are there any particularly frameworks or approaches that the company already uses to make decision? Ex: first principles thinking, STAR method, etc. Knowing these frameworks will give you a chance to frame your solution in a way that will resonate with the interviewers.
Be sure to ask any clarifying questions if you’re unclear about instructions on the take home
What have you seen in other candidates’ solutions that have helped them standout?
3️⃣ Call with other Leaders/C-Suite
Once you’re past the take home stage, you’ll most likely have a chance to meet with other leaders at the company. This is a crucial moment in the interview process because you’ll begin to meet the people you’ll need to get buy in from, work closely with, and, ultimately, help make the decision on whether you’ll land the job.
You can use the same intro, but personalize it to the executive. When meeting new members of the leadership team, you might be asked to re-introduce yourself. Feel free to use that same 5 sentence pitch but customize it the department you’re interviewing with. For example: “I’m excited to work on XYZ product because…”, “In the past, my relationships with the CTOs of the company were… and I’m hoping to expand that in this role by…”, etc.
Be wary of using the same anecdotes over and over again. Your interviews with other leaders will be a combination of behavioral and situational conversations. It’s a chance to get to know these team members better but also a chance to showcase your experience when working with other departments. Prep situations where you might have worked with members of different departments and try to have one for each function of the org. That way you’re not repeating the same cross functional marketing initiative story when you’re speaking with the CTO. It’ll show a range of experience and the ability to work alongside a variety of departments.
Build coaches within the company along the way. You’ll want to have as many advocates as possible while you’re interviewing. In the Chief of Staff role, relationships with the team are just as important as the relationship with your principal. Meeting with other key stakeholders should not only be about learning their perspective on what’s important to have in the role, but to win them over and build groundswell on your behalf.
Be prepared to answer how you think about the Chief of Staff role. How might you categorize the work deliverables you own and how are you planning on measuring success? Compare that with what you’re hearing from other leaders - how might they understand that you’re fulfilling your role within the company?
Questions to ask at this stage:
What keeps you up at night? This is a great question to understand what the rest of the leadership team sees as the biggest blockers at the company.
Follow up: Match your own skills and accomplishments to what you learn in this question and have a handful of examples you can talk through.
What are the top traits and competencies you would like to see in a Chief of Staff to the CEO?
Where do you see a Chief of Staff unblocking the principal/CEO most?
4️⃣ Final Call (Pre-Offer)
At this stage of the interview, you’re in the home stretch. Get ready to talk about potential salary expectations, start date, ask your final questions, and provide references.
Take initiative to show that you want THIS job. One candidate I recently worked put together a deck before her final interview with the exec (if you do go this route, always stay under 10 slides!) reiterating “Why me?” and sending it to him for pre-read the day before they met. Not only did this showcase her proactive nature, but she also knew that communication and presentation skills were key traits for the role so it gave her a creative opportunity to highlight this as a strength.
Know what your own salary expectations are. If you’re working with an external recruiter like myself, you can be as transparent as you’d like. A good recruiter will let you know if what you’re looking for is in line with what the company has budgeted, or if it’s too low or high. I like coming up with a “walk away” number with my candidates - the salary number that would cause them to shut down their job search and say yes to this role. If you’re negotiating on your own behalf, knowing this number will help you make a decision if you’re deciding between things.
Ask about Day 1 priorities. Knowing what the immediate needs of a company are will help you start to put yourself in that role. Offer up projects you would start to initiate if hired that directly address these pain points and give your potential principal an idea of what it would be like to work with you.
Learn as much about the culture and working style of your principal as you can. Understand if you’ll be force multiplying or complementing this principal and what are the avenues that are afforded to you for growth. Ask about how the principal best likes to work, how they like to receive feedback, what are the best modes of communication, etc.
This part of the interview process is you interviewing the company as well as them interviewing you. This is a crucial step that many candidates forget while going through this process. Know that a Chief of Staff role is unlike any other role you’d take. The relationship between Chief of Staff and principal has a level of intimacy unlike all other reporting structures at a company. Ask questions that will help you determine whether or not this role is going to help you get to where you want to be career wise and if the principal is someone you feel you’ll be able to build a long term, trusting relationship with.
Questions to ask at this stage:
Do I connect with these people? Can I show up as my full self?
Are there any past or current employees I could talk to to learn more about the culture of this company?
When do you expect this person to start?
Are there any additional pitch decks, product demos, etc. that I could view about the company?
Have other questions about the Chief of Staff interviewing process or is there something I missed? Let me know by submitting a question in the below!
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!
StarTree - Chief of Staff to the CEO
Industry: User-Facing Analytics, Enterprise Data
Series B, raised a total of $75M, founders are ex-Uber and LinkedIn
Location: SF/Bay Area based
Preferred Qualifications:
Experience working for or with enterprise infrastructure software
Experience working at a tech company
Experience with strategic cross functional initiatives, understanding of the software industry/technology, interaction with product and engineers, business understanding, board relations
Web3 Platforms - Chief of Staff to the CEO
Industry: People verification, Web3
Seed stage, found is ex-Facebook
Location: SF/Bay Area or London based
Preferred Qualifications:
Experience working directly on product development, go to market, HR, legal functions
Experience working in VC or fundraising
Summit Group Endeavors - Chief of Staff to the Chief Growth Officer
Industry: Events, Community, Networking
Location: Fully remote, US Based
Preferred Qualifications:
Background in marketing and operations
5+ years of overall experience
Demonstrated track record of customer engagement, acquisition, and retention throughout the funnel
Experience acquiring customers at a startup or growing business division that scaled quickly, ideally a consumer brand
Additional Chief of Staff Related Reads:
Who, What, When, Where: How to hire a Chief of Staff
How to Scale Yourself as a Chief of Staff
Consiglieri: Leading from the Shadows
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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 Elizabeth, Marissa, David for supporting the last issue!