Issue 12: The Relationship Between Chief of Staff and Executive Assistant
Effective partnership is not a given. Building a successful relationship takes time and effort.
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Welcome back, aspiring and current Chiefs of Staff!
📣 ICYMI, two weeks ago, I announced that I’ll be partnering with Ignition Chamber Academy to run its very first Chief of Staff School. There are so many aspiring Chiefs of Staff that have asked me about a course or certification that they can take in order to further bolster their careers and I’m excited to finally be able to point them in the direction of this school. In this 5 week course, we’ll cover the fundamentals that we feel like are helpful for any burgeoning Chief of Staff who is looking to step into the role for the first time.
Our inaugural cohort kicks of end of March and we’ll be accepting applications till mid March so apply today!
In this week’s issue, I’m featuring guest author Kathryn Montbriand. Kathryn spent a decade championing culture change at a Fortune 500 company before launching her own ventures. She pioneered a first-of-its-kind team of ‘Culturists’ that focused on employee engagement and creating authentic connections in the workplace. Throughout her time as a Chief of Staff, Kathryn has worked with several EAs and built a strong, foundational relationship with each of these individuals which has led her to greater success in the role than if she went at it alone.
How do you forge an effective EA & Chief of Staff partnership?
The best Chiefs of Staff know how to drive big results as a team of one. In this role, you typically have a small direct team, or no team at all. You must master how to work through others by partnering, finding common agendas, and leveraging shared resources.
One of the most important partnerships in this role is with the Executive Assistant: Get it right and you multiply each others’ efforts. Get it wrong and every day will feel more chaotic and less productive.
Having worked with Chiefs of Staff and EAs to build successful partnerships, here are 4️⃣ tactical ways to set a strong foundation between both parties:
1️⃣ Invest in the relationship: Assuming that you’ll get along with an EA is a common oversight. Get to know each other beyond the surface level. You need to be able to trust and rely on one another. Learn to build psychological safety with each other and get to know the whole person, rather than just the “work person.”
In the first few weeks of the role, spend time understanding the EA’s working style and top line tasks. Also take the time to understand the EA’s motivations for being in the role as well. Does this person have aspirations to become a Chief of Staff in the future? Or are they pointedly focused on being an extraordinary assistant and want to keep continuing to grow their skill sets in that capacity? Knowing these qualities about the EA will help you build your relationship. Some questions you can ask in the first 30/60/90 days to get to know your EA better:
What motivated you to come work for this particular principal?
What are areas of growth you’d like to invest in (and how might I be able to help you)?
6 months from now, what would our ideal working relationship look like to you?
Ask about their Meyers Briggs, enneagram, etc. These are all helpful jumping off points to understand the inner workings of an EA better.
2️⃣ Respect the incumbent: Chances are, one of these professionals is already in place when the second is hired. Ideally, they were included in the development and scoping of the other role, but if not, there’s still an opportunity to include them in the onboarding phase.
If you’re a Chief of Staff where an EA is being hired after you, take the time to sit down with your principal and write out this job description together. Take stock of the more tactical/administrative tasks that are currently on your plate that you might ideally want to pass along to an EA. Figure out how your time can also be freed up so that you can work on the things that are best suited to your abilities. A great EA should be a force multiplier for both you and your principal.
If you’re a Chief of Staff coming into an organization where the principal already has an EA, take stock of what the EA is already handling and even if some of those items could fall under a Chief of Staff role, don’t be so eager to take them over. Your job in the first few weeks is to absorb how things are being done and then suggest improvements if they contribute to the north star of your principal’s priorities.
3️⃣ Reduce overlap between the roles: Once the roles have been clearly defined, it’s important to stick to those roles. Chances are, your principal is firing off to do’s right and left and on occasion, there might come a task that feels better suited for the EA than Chief of Staff - maybe it’s scheduling an upcoming meeting or looking up venues for a future offsite. Instead of taking it on, this can be an opportunity to respect the boundaries of both your roles and either let your principal know that you’ll be delegating this task to the EA or if your relationship with the EA is strong enough, you can compare notes to redistribute tasks that make more tactical and strategic sense.
Having two people go at a task doesn’t necessarily make it more efficient. It doesn’t mean both parties can’t work together to get things accomplished, but it helps when there’s a lead and a support defined. One model for a tag team approach is the Batman and Robin metaphor. One person is going to take the lead and be the responsible one while the secondary colleague steps in to help out where needed and provides overall support. This working style also helps clearly delineate who is ultimately responsible for the outcome and should be the point person for the project.
4️⃣ Keep an open line of communication: Build up an operating rhythm with the EA where you check in with each other on priorities and tasks. From Hallie Warner, a former EA turned Chief of Staff, “Remember, you are both working on the same core mission – to ensure your Principal’s vision/agenda is clarified, communicated and executed throughout the organization. You are just accomplishing this mission by each using your unique skills and strengths.” A Chief of Staff and EA should be working in lockstep with each other and checking in regularly to continuously align.
I’m a firm believer that shared context enables everyone to move faster and more confidently. When partnering with EAs, I default to being inclusive with meetings, emails, and information. I encourage my EA team members to attend planning sessions and update meetings (as much as their calendar allows) and have an end-of-week 1:1 where we compare notes and strategize for the upcoming week. This way, we spend less time playing telephone and more time driving results.
At the end of the day, the relationship you have with the EA to your principal is just as crucial as the ones you have with other members of the C-Suite. The relationship working at its best empowers you, your principal, and the EA to work at their most efficient and highest potential.
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!
Trinsic - Chief of Staff to the CEO
Industry: IDTech, FinTech, SecureTech
$8.5M Seed, 13 person team
Location: Remote, US time zones only
Preferred Qualifications:
5+ years experience, including time in an ‘operating’ role such as Chief of Staff or Bizops
Experience at venture-backed, early-stage startups
Experience or interest in security, identity, infrastructure, dev tools, or web3
Strong financial acumen with ability to: prepare for board meetings, own financial model and forecast, experience managing a P&L, help to raise a Series A in the future
LatchBio - Chief of Staff to the CEO
Industry: BioTech, Cloud, Machine Learning
$28M Series A, 12 person team
Location: SF/Mission Bay, in person, relocation available, in person 6 days a week
Preferred Qualifications:
Strong operator with experience at startups
Customer-centric mentality
Experience with recruiting, investor relations, operational processes, onboarding and more
Biology background optional, but bonus
🎥 Upcoming Workshops:
The Ask a Chief of Staff workshop calendar is starting to fill up with workshops led by Chief of Staff experts and industry leaders. Make sure to register for a chance to ask your questions live and learn from some of the top names in the Chief of Staff world!
March 8th: Discovering Your WHY as a Chief of Staff
March 13th: Establishing Trust with Your Principal
April 4th: Calendar Strategy and Meeting Management
April 12th: Deciding What Comes After Your Chief of Staff Role
If you want to watch any previous workshops, subscribe to our YouTube page: www.youtube.com/@askachiefofstaff
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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 Emma and Lil for supporting the last issue!
Hi Clara! Will the events be recorded? I’m currently splitting time between Australia / Japan so it’s hard for me to make them 😅