How to Hire & Manage an Executive Assistant (EA)
The right assistant can feel like family. 🥹💙
It’s one of the most powerful yet underrated relationships. It’s worth figuring out how to do it well. Here’s what I’ve learned.
95% of having a great CEO x EA relationship is selecting the RIGHT person. Like most things, it’s about people, not tactics. 🙃
Tactics are great, but no amount of tactics can make up for having the wrong person in the role.
So - this post is broken into two sections:
Selecting the right person.
Tactics of how to work together.
P.S. Some context: My assistant, Leti, was hired through an agency called Persona. Leti lives in Uruguay (I’m in San Francisco) and supports me full-time. I’ve worked with a number of other assistants, both in person & remote.
For me, a 100% remote EA has been life changing. I imagine the right person who can be in person would be even more so (but I have yet to find that person). This piece is totally dependent on what you want this person to do.
Selecting the Right Person.
First, what is the role of an Assistant? It’s two things.
Taking work off my plate & clearing space in my mind.
Most people forget the 2nd piece of it, but it’s just as (if not more) important.
My EA’s job is to:
Take stuff off my to-do list.
Actually do tasks from beginning to end w/o my involvement so I can focus on higher leverage work.
Take stuff off my “mental plate”.
Let me delegate and forget about the admin that goes on behind the scenes. I.e. if I have to follow up to ask about the status of something & I’m holding it in my brain, that’s failure.
Half of the job is DOING the work, the other half is COMMUNICATING.
So, with that, here are the key areas I’ve found most important when finding an assistant: Integrity, Availability, Intelligence, Speed, & Desire.
1. Integrity.
This person knows everything about my life. She has my google account, my passwords, my credit cards, etc. This is what makes her effective. I *could* technically not give her access to any of that, but then she would be 1/100th as effective as she is now.
Either way, Integrity is #1.
Can I trust this person with my life (literally)?
The answer is, you won’t ever know for sure and you’ll have to take a leap of faith. Trust is earned over time, but there are some ways to lower the risk.
This is why I generally go through an agency instead of hiring direct (on Upwork, etc.). Agencies do background checks, they have backstops if something happens, etc. We use Persona (have tried Athena, but have found better talent with Persona).
Then, figure out their goals with the role. Are they looking for a long term position? A career? This is a helpful indicator. Look for tenure in past roles. Also can just ask them how they’ve handled other people’s sensitive information in the past or try to see if they’ll give you information about a past employer (bad sign).
But mostly — go with your gut. If something feels off, just listen to that and keep searching for someone else.
2. Availability.
I need my EA to be on my schedule. And my schedule is…unpredictable, relentless, and basically 24/7. 😅
So in the interview we asked Leti if she could be available 24/7. Without hesitating, she said, “absolutely”.
Of course, I don’t actually expect her to respond 24/7 or even ask her for that, but I wanted to get her gut reaction to that question. I wanted to set the expectation that this wasn’t going to work if she wanted strict bounds on her schedule. I need someone flexible & down for the unpredictability. This is just the reality of my life — and this person would be supporting my life.
I’ve found there are two different types of people.
People who get drained from being “on”.
These people need more predictable schedules, need to recharge by being offline, etc. They’re overwhelmed when things change.People who are energized from being “on”.
These people are the ones who are always on, even in their personal life. They respond quickly and have insane energy. They aren’t bothered by a change in schedule.
I wanted to find the 2nd. Someone who was going to be energized by being on & supporting me (these people exist!).
And it works. It’s who she naturally is.
Main thing — match your EAs schedule to yours. And be direct about what you want.
3. Intelligence.
This is a big differentiator. The specific competencies depend on what you actually need support with, but I’ve generally found raw intelligence as a major multiplier for this role. “Intelligence” for this role means organization, clear communication, juggling many balls in the air, taking on complex tasks, and more. This will determine the level of work someone will be able to take off your plate. Note: it’s intelligence, not experience.
There’s lots of ways to screen for this, but here’s some gut checks that will help you know if you have the right person.
Give feedback, but only once. Everyone needs feedback. But a great EA should not need the same feedback more than once. I asked my EA to send me updates EOD. They were too messy / unorganized so I sent her a screenshot of how someone else formatted their messages as an example. The next updates she sent were incredible — even more organized and succinct than the example message.
Fast learner. The role is broad & they need to be a generalist. They cannot rely on experience — most everything will be 1 off or new. The key skill is being a very fast learner & having a “figure it out mentality”. If they hit a wall, they figure it out instead of coming to you for everything. They are able to handle complex and/or ambiguous tasks. i.e. I had an issue w my health insurance & I asked my EA to figure out “if I had a PPO or a POS” — she took that and ran. She used ChatGPT to learn the differences, called the insurance company, called our benefits administrator, googled it online, etc. and came back to me with an answer. She didn’t know what a “PPO” or a “POS” was in the beginning but she learned it through the process & gave me an answer within 24 hrs.
Peace of mind. If you’re constantly wondering if something got done and having to follow up or if you’re consistently pointing out missed tasks, it’s not working. This is a sign the person cannot juggle multiple things or handle the chaos of the work. This was a common theme with other EAs who didn’t work out. I thought it was my fault that I was piling too much on or giving too much sporadic work. But that’s their job — to handle the piles of admin stuff and keep it organized. You deserve someone who can do this & give you peace of mind. When I hired my current EA, she was able to do this with zero training (and she hadn’t been an EA before).
4. Speed.
This is a combination of availability and intelligence, but worth its own point.
How quickly do they respond and how quickly do they get tasks done?
It’s not just that a person can DO the hard work. They also need to be able to do it quickly. Speed is a super power.
Notice this during the interview process. How quickly do they respond to your messages? This is a huge sign.
Once they’re on board, if you’re concerned someone is not getting enough done in the day - they’re probably not.
5. Desire.
Lastly, they need to want the job. If they only want to do certain tasks, it’s not going to work. If they want the spotlight, it’s not going to work. If they want to grow out of it in 6 months or a year, it’s not worth it. They need to want this. They need to be willing to take on whatever comes their way. You two are a team & your job is to split up the work between you as efficiently as possible.
There are people out there who love supporting, who love being in the background, who get immense pleasure from knowing they’re being helpful. They are truly ecstatic at the idea of this role. These humans are angels among us. Find them, invest in them, and never let them go. 💙
Tactics & How to Work Together.
You’ve found someone awesome. YAY! Now, how do you get the most out of it? Here’s the things that have worked with me + my EA.
1. Use a separate app to communicate w/o distractions.
I talk to my assistant exclusively through Signal. It’s the only app I get notifications from (not even messages, email, slack, etc.).
We text back and forth, and I send her voice notes throughout the day.
And the only people who I Signal with are 1) my cofounder 2) my chief of staff 3) our board member 4) my EA.
They are the only people who can reach me at all times. It cuts the noise & notifications out of my life.
It can be any app, but pick one that you can separate out from everyone else (this is why text messages and slack do not work).
2. Build a basic “preferences” sheet.
When they onboard, build a doc with:
Your legal name
Your home address
Your office address
Flight booking information
Key people (teammates, family, etc.)
The places they’ll book most frequently
Doctor, dentist, haircut, etc.
Anything they should know about you
Ask them to update this anytime they learn something new.
3. Use one pass for passwords.
Get a password app & create a shared vault (don’t add them to your vault — you’ll only want a subset of your passwords in the shared one). Use auto-generated passwords vs memorable words & phrases. Start with sharing logins to only what’s necessary and over time as you build trust you can add more passwords.
Add two factor auth (that you hold the keys to) for the important things.
And anytime you switch an EA, change all your key passwords.
4. Ramp up intentionally.
Great EAs can be effective on Day 1. Give them quick admin tasks that don’t require context. Logistical stuff, booking restaurants, etc. are great options.
Then give 1 major learning area per week.
i.e. 1 week to master scheduling, 1 week to master email triage, 1 week to master email responses.
And do FULL ownership in each of these. “Success at the end of the week means that you’re able to separate important vs. non-important emails in my inbox by EOD every day. You own flagging to me when an important email comes through.”
Failure modes:
We split ownership 50/50
I ask them to master 2+ things at once
5. Get them a phone number.
Make sure your EA can make calls. (And speak fluently in whatever language you need them to.) They can create a Google voice number or some other number — but they should be able to call & talk to people on your behalf (think: restaurants, hotels, doctor appointments, etc.).
6. Use voice notes.
I send voice notes via signal. It’s faster for me to send notes via voice than text when I’m between meetings. The voice notes can be sped up so it’s easy for Leti to listen to. Voice notes also translate tone. She’ll text me back (I prefer sending voice notes but receiving text so I can quickly glance at it between meetings).
If it’s urgent, I’ll send a voice note then send a text after saying “URGENT ^” and point to the voice note so she knows to listen asap.
7. Have them confirm everything you send.
Leti acknowledges everything I send. Even if it’s just a thumbs up on the message. It helps us get on the same page with what she’s working on & gives me peace of mind that she’s seen it. She’ll also let me know throughout the day when each thing has been done, instead of keeping me waiting for a single recap. These small things add up to a frictionless relationship.
8. Over-communicate.
Leti is the one person I am texting back and forth with the most (even more than my husband 😅). Over-communicating (esp. in the beginning) builds trust. She’ll let me know when she’s up every morning, when she’s done with daily routine tasks (checking email, etc.), and when she’s heading offline or going to bed. In a remote world — these basics are really helpful. I’ll tell her, “I’m heading to dinner so won’t answer for next hour,” etc. She will do the same. Seems simple but little things like that are huge for our relationship.
9. Ask for an end of day recap.
Leti sends me an end of day recap with the updates I need to know one by one. Formats it with an emoji + bold title to make it SUPER easy on me to understand what it is at a glance & know if I need to do something. One by one is key bc I can reply to each individually (either with an emoji or an actual Signal reply, which will thread the original message).
10. Create rules for scheduling.
Scheduling will always be a back and forth — especially if you are insanely protective about your schedule and anal about anyone putting time on it outside of you (this is me 😂).
What’s worked — defining blocks (no matter how small) that my EA can have carte blanche to schedule in.
For me: 12-4PM PST Mon, Tues, Wed & Fri.
How it works:
She goes through my email and makes a list of all the meetings I need to schedule.
She texts me the list.
I send her a voice note of what to prioritize & if there are any exceptions to the 12-4 rule.
She schedules them within the approved time blocks & puts it on my calendar.
11. Build a system to triage email.
Leti goes through my inbox every morning and:
Marks all spam, receipts, & unimportant stuff as “archive” —> this goes to a separate inbox where I can quickly go through & archive (I do all the archiving - she does not actually archive or delete anything)
Screenshots important / urgent emails & sends them to me via signal
Makes a list of everyone I need to schedule with & tags as “pending scheduling”
Updates any purchases in a “purchases & returns” tracker spreadsheet
She makes sure I get my returns done in time, etc.
Looks up candidates who cold email me, finds their linkedin, & gives me gut check on whether I should take the call
Another trick — create a label with your EAs name. Create a separate “inbox” (gmail or superhuman) for these tagged emails.
Then when you go through your email, you can tag her on emails you’d like her to handle.
12. Document learnings.
Once she’s learned something, she writes up a doc + makes a loom on “how to” so we have it for the future if we need to train someone else on it. She does this for any new task she takes on + documenting my preferences.
Every doc + loom is stored in a notion database.
13. Force yourself to delegate.
Learning to delegate does not come naturally. A great EA can take on way more than you initially think. You have to train your brain in this new working relationship. Here’s how:
Write your to do list out. Then ask yourself, “if my EA HAD to help me with each thing on this list, how would they help?” —> then write how they’d help next to each thing. It’ll open your mind to how much they could be supporting, even on higher level work.
Example:
Write Investor Update —> Ask Leti to grab key wins from each teammate.
Fill out form for doctor —> Ask Leti to screenshot the form and send me questions one by one so I can voice note her the answers.
Do dry cleaning (that I’ve been putting off for a year 😂)—> Ask Leti to check pricing for drop off / pickup dry clean service in SF.
14. Get all EAs at a company to know each other + share tips.
If multiple people on your team have EAs, this can be a force multiplier. We’re starting to get more admin support because we’ve found it’s insanely cost effective & they’re able to do super high leverage work (i.e. my EA builds my slides for Monday morning all hands).
15. Be human and care about them as a person. 💙
This job can be thankless sometimes. It’s a heroic effort behind the scenes and when you find a great person, they become family. This person is literally an extension of you.
So it’s been really rewarding to slowly build a relationship.
Take the time to be human. Laugh at the funny stuff that comes up, ask about their lives, get to know their family, etc. It’s worth it.
TL/DR: Invest in this relationship. It will pay off.
Leti is coming to San Francisco to visit this year — I couldn’t be more excited. 🤩