One of the Most Important Hires You’ll Make: Hiring Your Executive Assistant

Recently I was on the phone with the CEO of what I believe is one of the most interesting startups of the past decade. We talked about his vision for the first ten minutes or so. At some point we turned to what he is most concerned about right now. His answer was that he wanted help hiring an Executive Assistant (EA) and didn’t know who to ask for help. He wasn’t sure what to look for in an EA or how to write the JD, he didn’t know where to look and he felt confused about how to take the first step. There are countless resources to hire most roles for a technology startup, but the EA role is not one of them. 

“How do I hire an EA?” It’s the type of question I felt insecure asking our investors about even though I think it’s one of the most important hires a CEO can make. It creates, or destroys, leverage. I can think of several CEOs, including those of unicorns, who won’t pull in their EA to help with calendaring “because my EA is really bad but I’m afraid to fire [her/him]”. Conversely, I had an EA as CEO that made me dramatically better at my job (and helped provide awesome leverage for the company).

When to hire an EA: At a VC’s CEO conference I attended about five years ago, a CEO brought up the challenge of knowing when to hire an EA. After some quick polling amongst the 80 CEOs in attendance, it seemed like internal communication and internal ops tend to break down when the company reaches about 50 people if there is no EA. I think that likely changes based on how intense your meeting culture is, and your need for outside meetings (i.e. B2B companies or companies that depend on partnerships likely have more), but I found 50 people to be a good rule of thumb. Having said that, many second-time CEOs/founders do it earlier because they recognize how much leverage and value the role creates. When cost is an issue, as it is for many companies, I’ve seen a virtual assistant to be very effective

Defining your hiring traits: This is a macro point for all roles at the company: define the hiring traits that you won’t compromise on. For me that was integrity, work ethic, intelligence, pride and teamwork. I don’t care if a candidate is funny or likes sports. I don’t care about the airport test. I find that when we use phrases like “cultural fit” without defining what that means, it leads to bias and hiring people that look like you rather than hiring someone that will be a great teammate in your org. Take time to lay out, and then institutionalize, the hiring traits you think will lead to the culture you want. Think about how to clearly articulate these traits to the team and how to probe for them in an interview. How can you reinforce them both in hiring and throughout your culture? 

Defining this role and your relationship: What do you need from your EA? For many CEOs the central requirements are calendaring items, organizing meetings, booking travel, coordinating lunches/dinners with the senior team, managing your agenda as a gatekeeper, handling expenses, ensuring the CEO actually eats lunch and maintains a healthy schedule (i.e. fighting to keep your dentist appointment or yoga class on the calendar). Your asks may include personal items like organizing personal travel or helping with a restaurant reservation — whatever you think is appropriate. But the key is to think ahead about what support you want, and build that into the job description. 

Will other teammates have access to this EA to help with calendaring their meetings? What if some senior teammates have access and some don’t? Does this EA report to you, and if so are you doing weekly 1:1s (as you would with other direct reports) or does it make more sense for the EA to report to someone else and do monthly check-ins with you? Answer those questions for yourself and make sure expectations are clear up front. 

Is this person an office manager or an EA?: A confusing topic for many first-time CEOs is the difference between an Office Manager vs. an Executive Assistant. Frankly I’ve never found a good definition, but based on my experience I would say an Office Manager typically does the following things: 

-orders office supplies/food

-may supervise the work of other support staff (I.e. Exec Assistants)

-helps keep office policies up to date 

-coordinates teamwide events (offsite, lunches/dinners, etc)

-tends to support the needs of the office more broadly while an EA tends to focus on one or more executives

I’ve seen, and worked with, people that do both jobs for a period of time — splitting their role between OM and EA. I think this works for 6-12 months, but it’s strenuous to jump between both roles, hard to maintain, and can lead to burnout. 

Limiting the role: More than any role at a startup, I’ve seen the job responsibilities of an EA creep over time without clear definition. Other executives will ask for support, sometimes without clearing it with the EA’s manager. Will the EA help with offsite or other tasks that traditionally fall to an Office Manager? Defining what the EA will not do in the role is important.

Create a (unique) job description: You need a job description. Try to include some personality — try to show who you really are. Also, don’t hold back on the actual tasks you want done. If you need the EA to bring back lunch for you every day or schedule dentist appointments because you haven’t found time to do that for seven years (as is the case with one CEO I know), don’t be afraid to mention that up front. Be specific about what you want while clearly laying out the hiring values you want (see above).

No surprises — make it clear what you’re like to deal with: Consider publishing a User Manual for yourself. In the absence of that, think about providing your 360 reviews to final round candidates and allowing them to speak with references. Changing EAs is exceptionally painful, and helping candidates know what you’re like to work with upfront, especially the warts, will only help everyone make a better decision.

Set up the hiring process: Who should be on the hiring panel and who should be the initial screener? I recommend the CEO not being the initial screener but certainly providing signoff before the hire is made. Consider running a hiring funnel similar to B2B sales. Don’t use a recruiter for this role. I think recruiters are great for executive hiring, but for an EA (and most other IC, non-exec roles) I’ve found them to be much less effective and often counterproductive. Focus on candidates that have experience with companies around your size and pay particular attention to how long they stay at each position. Multiple stints of one year or less is a deal killer — turnover for this role is just too costly and you want to focus on someone who has demonstrated they will stick around. 

Onboarding and ongoing communication: The first 10 days after a new teammate joins the company is a huge predictor of longevity, regardless of role. Are they meeting other people? Are you communicating what’s working (and helping to adjust what’s not)? Don’t just leave them to figure it out on their own — provide feedback. Set up recurring 1:1 meetings, even if the EA doesn’t report to you, where you can both talk openly about what’s working and what’s not. Ensure that whoever is managing the EA is providing appropriate feedback and learning the EA’s professional development goals. 
Preparing for inevitable turnover: While I’ve mentioned several times how painful EA turnover is, it is almost certainly inevitable. I don’t know of a single CEO who has kept the same EA throughout their entire tenure. Try to limit the pain by encouraging tasks to be institutionalized — i.e. through Standard Operating Procedures. Capture how you like calendar invites to occur (format, who sends, etc); where, when and what you like to eat; travel guidelines, etc. Effectively, you’re trying to create a document that allows the next EA to step in as seamlessly as possible.