A founder's guide to hiring the right EA

There’s a moment every founder hits when they’ve reached their capacity ceiling. You’ll know you’re there after weeks of non-stop meetings with no clear rhyme or reason and feeling like you don’t have time to actually get anything done. If this sounds like you, you need to hire an EA.

I’m 100% biased but I’ll be the first to tell you that a great Executive Assistant is one of the most important yet overlooked hires you can make. Not because they’ll manage your calendar, but because the right EA gives you back the one thing you can’t get more of: time to focus on your actual mission.

Finding a great fit for the job is straightforward enough, but there are a few nuances that most founders miss on the first pass at hiring someone for this role:

Hiring someone for the wrong stage: “Seasoned EA to a top exec at XYZ Corp” sounds impressive on paper. but an EA to a startup founder is completely different than an EA at a Fortune 500 company.  At a big company  systems already exist. There’s structure, process, and usually some kind of clear-cut handbook to reference. The job is to plug into it and run it well. In a startup, none of that exists yet. Your EA isn’t following a system, they’re identifying where things are messy and streamlining as they go.

Hiring someone that doesn’t match your working style: another thing most people miss at first is that even a fantastic EA might not be the right one for you and your working style. I know dozens of incredible EAs and none of them would be the right fit for each-other’s bosses - it’s a two-way relationship. Just like you can’t do a seamless spouse-swap, you can’t pair just any great EA with any competent founder, there has to be some degree of working-level chemistry there.  

Not knowing what you really want: understand how you want to leverage your EA before you make the hire. Do you want someone to just step in and really nail your calendar or do you want to take the time to build  a strategic partnership?

Ask about working style early: ask how they think about hours and availability. Even if the role is technically 9-5, the reality is you don’t control when things come up. Travel emergencies, last minute changes, early mornings. You don’t need someone who’s always on, but you do want someone who understands that the job doesn’t always happen neatly between business hours and is willing to step in when it matters. 

Get clarity on what they actually enjoy: it’s also worth understanding what they actually enjoy about the job. Some EAs love juggling multiple execs at a more boiler-plate level. Others prefer working really closely with one person  and being in the weeds with them. Key answers that indicate someone wants to build a partnership with you and understand your business will include things like preparing notes ahead of cold meetings, drafting follow-ups, managing your inbox. Answers like complex calendar management, travel planning, and expense reporting tend to point to a more traditional EA role. Neither is better but they function very differently, you want to make sure their interests line up with what you actually need. 

Test how they think, not what they know: give them incomplete scenarios you’ve actually dealt with and see how they would have responded. For example, lay out a situation in which your flight lands at 4am and you have an important meeting to get to by 10am. A strong candidate won’t just think about booking a flight and making sure you know where the meeting is, they’ll start piecing together the gaps. Where are you going in between if check-in isn’t until 3pm? Do you need a car or does that city have a strong Uber population? Should you book the hotel for the night prior so you have a landing pad? Do you need a workspace for the day? Their answers don’t need to be perfect but they should give you insight into how they think and whether they’d catch the things you’d care about in the given situation. 

Ask about mistakes: have them walk you through a time they messed something up and what they did after. You’re looking for whether they can be honest about it, take ownership, and explain exactly how they adjusted moving forward. The best answers aren’t always  polished but it’s important to pay attention to how a candidate talks about mistakes they’ve made. Not only should you be able to have a clear understanding of how they handled the error  and made a plan for how to avoid similar ones in the future, but you’re also identifying the types of mistakes they make. “Early in my career, I didn’t realize XYZ should happen but after one time, I never made that mistake again” signals the ability to learn and grow. Whereas, “one time, I forgot to book a plane ticket because I took on too much at work” indicates a level of carelessness. You’re looking for someone who can say “I screwed that up”, fix it quickly, and not repeat it. 

I’ve spent 12+ years working alongside founders and their EAs, and I can tell pretty quickly which are linchpins and which are causing avoidable roadblocks. Here are a few tips.

Hiring the right EA

If I could give you two tips on hiring a truly incredible EA, the first is to ask the question “where do you see yourself in 5 years” without being afraid of the answer. The hard truth is that in 5 years, a strategic-minded EA might no longer see themselves as “just an EA” and that’s okay. That doesn’t mean they aren’t a great fit right now. It also does not mean they’ll outgrow you, if you’re willing to give them more responsibility over time. 

Truthfully, most of the best EAs I know aren’t actually EAs anymore – they started as EAs but grew to be a lot more. But, they all still work for the same companies, even 10+ years later. And they’ve been there to train their replacements for absolute success and become a long-term resource to that person - if and when the time came for them to transition into another role that fits their skillset when the need arises I’ve seen great assistants pivot into a wide variety of roles, like Chief of Staff, Head of HR, Talent Team Member, and VP of Operations. 

Resumes aren’t always a great indicator here. “Strong experience in Google Suite” isn’t going to make or break a candidate. Software and tools are ever-evolving and can be learned quickly, and honestly, sometimes too much experience just means someone is used to operating inside someone else’s business model.

This is where tip two comes into play, don’t be afraid to hire someone green who can grow alongside you. Answers to the daunting question of “where do you see yourself in 5 years” that include ambitions to evolve into a larger role, or even something along the lines of “I want to continue evolving into the most strategic partner to my exec” are bright green flags here. If you’re still unsure, take this a step further, ask them what they’re reading, where their interests lie. A surprising number of people I speak to  seem genuinely surprised to find that EAs read books on professional success and productivity - a huge indicator that there’s significant room to reevaluate how we’re thinking about people in these roles. 

Basically, what I’m trying to get at here is this: what matters is grit, and that can be hard to gauge on paper. 

The best EAs are scrappy, proactive, have strong business intuition, and high emotional intelligence. They don’t just complete tasks, they look around corners and make calls without needing to check in on everything. They can finesse last-minute cancellations, get you the refund on that flight you cancelled minutes before take-off, and help talk you off a ledge during the stressful times.

The easiest way I’ve found to filter for the right qualities  is to give your candidate a scenario with incomplete information and see how they react. Treat them like a potential associate hire and present them with a case study of actual situations you’ve encountered and see how they think through each problem. A poor candidate will miss important details and ask the wrong questions. A mediocre candidate will give you answers indicating a little bit of fear related to autonomous thinking. A great one starts piecing together what you’d probably want and start asking the right questions to confirm they’re on track.

It’s also worth remembering that this goes both ways. The best EAs are evaluating you just as much as you’re evaluating them. They’re paying attention to your values and how you communicate, and asking themselves is this someone I want to go to bat for repeatedly? They’re also looking for signals on whether you’re open to their ideas and a bit of operational help, or if you’re still keeping a tight grip on everything.  They’ll notice how you react when things don’t go your way and whether that aligns with how they operate. There’s no “right” personality here, it just matters that you’re honest about how you work. 

Train them to think like you would

Many founders rush EA onboarding because they’re already overwhelmed, which is the whole reason they hired an EA in the first place. Then they get frustrated when the EA asks too many questions or makes judgement calls they themselves wouldn’t have made. It’s important to take the time here to let the EA into your thought process so they can start learning to think the way you do. 

Tactically, come prepared for their first day - spend time writing out how you hope to spend your time, when your ideal working hours are, which types of meetings you take and how to triage them, ideal spend parameters for regular events (travel/dinners/etc). Hint: you’ll know you’ve made a great hire if they come prepared to your first day 1:1 with a list of these questions for you.

Early on, explain in your own words how you think and how your business works. Not just what your calendar looks like, but why. What gets priority, who always gets time, when you need buffers, if you prefer morning vs afternoon working blocks, what a “good day” actually looks like versus a chaotic one. This doesn’t have to be concrete but it should serve as a starting-point. Founders, of course, haven’t always thought these things through explicitly and these can be working concepts that evolve over time. The goal at this stage is start thinking through these things together so your EA can help strategize in the long run.

From there, the first couple of weeks will necessarily be pretty high-touch. Ask your EA to copy you on all emails so you can start to identify in real-time if there are any adjustments you’d like them to make - and take note of how they implement those changes moving forward. An EA who understands your business can manage priorities, not just logistics. When they know what actually matters right now, they can make the right calls without pulling you in every time. With a bit of guidance, they will evolve from a human Calendly page and start acting more like a gatekeeper.

A dream of a perfect EA world

Forget everything your grandpa told you about his “secretary”. Your EA can be just support (totally fine, if that’s what you’re looking for) or they can start to function like your real-life business clone that doubles your capacity.

Dream with me here, a world exists in which you’re at inbox zero on a (semi) regular basis. You have a true teammate that you can loop into an email to a high-value potential customer and trust with absolute certainty that it’s going to get handled with the level of care that you would (maybe even better) and at any point, you could ask for the status of every outstanding email and get a clear answer within minutes.

Now let’s take that one step further: you’ve given them inbox access and they’ve drafted replies in your tone of voice so all you have to do is skim and send. They’ve armed you with meeting notes ahead of your day so you can walk into unfamiliar waters and quickly remember why you’re talking to Bob from XYZ company and find your footing - even though you’ve been in back to back meetings all day. And afterwards, they’ve also drafted a follow-up for you (in your tone)  based on templates you’ve sent in the past.

This is when everything clicks and you get to be one of those CEOs bragging about how your EA “just gets it”, almost like you’re doing a brain-share.

What if I’m not ready to commit to a full time EA?

Truthfully, I go back and forth on this. My instinct is that part-time EAs can reinforce the idea that this role is purely tactical and I tend to worry that the experience of a subpar EA may tarnish the way founders think of this role long-term. That said, it doesn’t have to play out that way. 

Hiring a part-time or contracted EA can be a good place to start. If you’re not ready to commit to a full-time hire, it’s a lower risk way to build trust and figure out what you actually need. And if you find the right person, they can still be a strategic partner. 

The tradeoff, and it’s a big one, is that it’s much harder to find someone truly great in a part-time or service model. They do exist in this space, you just may have to onboard and off board several different people to find the right one, which takes time. If you do choose this route, I’d suggest tapping your network to find a specific person, rather than relying entirely on a platform. And even if it’s limited hours, make sure they have some flexibility for things that don’t fall perfectly into a set schedule. 

If you find someone that’s a great fit in this capacity, you can almost always scale up once you’ve established a relationship. 

Recap

The “perfect” EA doesn’t exist. But you can find and train the perfect EA for you.  From the jump, there should be some level of understood commonalities and a clear understanding of what you’re both optimizing for. It’s someone with the right amount of grit and drive to learn— someone hungry, who’s been given enough context, trust, and reps to become indispensable.

Most founders eventually get there, but my hope is to help you navigate the early days and avoid going through the tough moments, like EA getting names wrong, coming across as rude, or forgetting to book you a hotel for your business trip, and get you to the good stuff more quickly. That takes time, effort, and a clear roadmap for laying the right foundation. 

If there’s one thing I hope you take away from this, it’s that investing early in finding and shaping the right partner is what will allow you to come up for air and create space to focus on the problems that you’re actually passionate about solving.