One of the first questions I ask every startup founder during a recruiting intake call is:
“What are you looking for in your Executive Assistant?”
The answer is surprisingly consistent.
“I need someone who can help me leverage my time. I’m overwhelmed. I’m spending too much time on administrative work, sitting in too many meetings, and not spending enough time on the things only I can do.”
Then the list starts growing.
“I’d love for them to manage my inbox, draft emails, own my calendar, schedule meetings, and be strategic about how I spend my time. They should be a thought partner.
It would also be great if they could handle office management - inventory, team lunches, swag, events. Oh, my co-founder will probably need help, too.
We’re hiring quickly, so they’ll need to coordinate recruiting, create a great candidate experience, onboard new hires, and help with People Operations. We’d also love someone who can be an extension of me and the company and represent us well with external guests and VIPs.
They should be trustworthy, hardworking, responsive, low ego, adaptable, incredibly smart, and preferably have already supported a CEO at a fast-growing tech startup. We don’t have much time to train them, so they need to hit the ground running. We also need someone with good judgment and intuition.
Oh, and they should already be using AI, building workflows, creating automations, and have examples of how they’ve made themselves, their exec, or their teams more efficient.”
Every founder wants this person.
The challenge is that they’re describing a unicorn. Also this is three jobs in one, but that’s a story for another time.
After interviewing more than 300 Executive Assistants over the past few years, I can count on one hand the number of candidates who truly check every box.
So instead of asking, “Where do I find this person?” I encourage founders to ask a different question:
What do I actually need today?
What are the highest-leverage problems your EA needs to solve in their first 30 days?
What can you teach over the next six months?
And what are you willing to pay for the expectations you’ve set?
The biggest mistake I see founders make is optimizing almost entirely for experience.
Experience matters, but it’s rarely the thing that predicts long-term success.
I’d hire someone who is exceptionally smart, trustworthy, curious, adaptable, and eager to learn over someone who simply has the “perfect” resume.
Hard skills can be taught.
Soft skills like judgment, work ethic, integrity, and emotional intelligence are much harder to teach.
The other thing I would also never compromise on is personality and culture fit.
Your EA is going to be your closest business partner. They’ll see your best days, your worst days, and everything in between. If the partnership doesn’t click, it doesn’t matter how impressive their background is, the relationship will be doomed.
Look for someone you feel like you could trust. Find someone who thinks the way you do. Find someone with the potential to become the Executive Assistant you need - not just the one they are on day one.
Because the best Executive Assistants aren’t always hired.
Many of them are developed.
YES, all of this!