Executives, if you’ve had four Executive Assistants in three years and “none of them worked out,” I have a question:
Were any of them actually Executive Assistants?
Because I hear versions of this story all the time.
“My friend’s daughter just graduated from college. She’s really organized and eventually wants to go into marketing, so I thought she could be my assistant for a while.”
“She used to be an office manager for my chiropractor and was great at that.”
“She likes people.”
“I trust him completely so he should be able to do the work.”
“He really cares about me and knows how I think.”
Wonderful. None of those things makes someone an Executive Assistant.
I recently had a discovery call with someone wanting 1:1 coaching who was refreshingly candid about this. He had been a lifelong professional musician. No corporate background. No tech background. No previous Executive Assistant experience.
His best friend is the CEO of an AI startup. He started hanging around the office, helping with little things, and eventually his friend asked him to become his EA.
Why?
Because the CEO trusts him. Because he knows his friend cares about him and has his best interests in mind.
Those are valuable qualities in an EA. They are not the qualifications for being one.
And sure enough, the CEO had already gone through four or five Executive Assistants in approximately three years.
That is where the hairs on the back of my neck start standing up.
Let’s Reverse This for a Minute
I asked this gentleman a version of the following question:
Imagine I called you tomorrow and said, “I’ve been an Executive Assistant for 27 years. I love music. My best friend is starting a band, and she really trusts me. So I’m going to try to play bass. It’s not really my thing, but can you give me some pointers on how I do it?”
You would rightfully think I had lost my mind.
You would not hand me a bass guitar, put me onstage Saturday night, and then get pissed at me when I couldn’t play the set.
Yet executives do exactly this with assistants.
Then six months later:
“She just couldn’t anticipate.”
“He wasn’t organized enough.”
“She couldn’t manage my calendar.”
“He wasn’t strategic.”
“She kept missing things.”
Of course they did. You hired someone to learn the instrument during the concert.
This particular person even acknowledged that organization, follow-through, and completing projects are not naturally his forte and that he is essentially trying to “rewire” his brain for the job. He is four months into learning an entirely new profession while supporting the CEO of a venture-backed AI company.
That is not an indictment of him, at all. Frankly, I respected his self-awareness enormously!
It is an indictment of the hiring logic.
Being an EA Requires Actual, Specific Skills
There is still this bizarre belief that Executive Assistant work is basically:
Be nice.
Answer some emails.
Book a flight or two.
Keep the boss from forgetting lunch.
Help him “get more organized.”
No. No. No. No. No.
A strong Executive Assistant supporting a serious executive may need to:
Build international travel from scratch. Not just buy a plane ticket—understand time zones, arrival times, sleep, ground transportation, meeting locations, visa requirements, buffers, meals, delays, 22 client changes, 13 executive changes, and whether landing in Singapore at 6:00 a.m. before a 9:00 a.m. client meeting is actually a remotely intelligent idea… In a location she’s never been to.
Manage a calendar with competing business priorities for a startup. That means knowing which investor meeting gets moved, which employee cannot be moved, what requires preparation briefings, what lunch should never have been accepted in the first place, and what three decisions will be created if you move one seemingly insignificant 30-minute meeting.
Read an executive’s inbox and distinguish noise from consequence within the first 30 days of employment. Who gets answered? Who gets elevated? Who gets declined? What looks unimportant but could actually affect a customer, investor, employee, board member, or deal?
Manage expenses without creating more work for the finance team. Exact receipts, coding, currencies, policies, missing documentation, approvals, reconciliations. Over and over and over again, with no room for error. This is your money we’re talking about.
Track dozens of open loops simultaneously. Someone owes you a deck. Legal needs an answer. The hotel confirmation is wrong. Tuesday’s meeting moved, which affects Wednesday’s flight. The CEO promised someone an introduction six days ago. None of these things can disappear because something louder showed up today.
These are not personality traits. They are professional capabilities.
Current EA roles routinely require years of senior-level support experience, complex domestic and international travel management, global calendaring, expense reconciliation, stakeholder communication, discretion, judgment, project tracking, and the ability to independently resolve conflicts and changing priorities.
There is a reason experienced Executive Assistants are good at this. We have been doing it for years.
You Would Never Do This With Other Functions
Imagine saying: “My best friend’s daughter just graduated with a finance degree, so I made her Controller. She hasn’t actually done accounting yet, but she’s great with numbers.”
Or: “My neighbor’s 18-year-old son spends a ton of time playing around with AI tools and playing video games. He likes electronics, so I brought him in to help architect our new AI product.”
Or maybe: “My friend is incredibly trustworthy and is a real people-person, so I made him our Chief Human Resource Officer.”
Sounds ridiculous, right?
Yet somehow, when the job is Executive Assistant, people shrug and think: Eh. She’s organized. She’ll figure it out.
And then the profession gets blamed when she doesn’t.
Trust Matters. But Trust Is Just the Beginning.
Would I want an Executive Assistant I trust completely? Absolutely.
Would I want someone who genuinely cares about me and the business? Of course!
But those qualities sit on top of competence. They do not replace it.
I spent 27 years doing this work. I spent a decade standing beside Simon Sinek, making decisions, solving problems, protecting his time, managing logistics, navigating relationships, fixing things nobody ever knew had broken, and carrying an enormous amount of responsibility.
I learned constantly.
I screwed things up.
I got better.
I developed judgment because I had thousands upon thousands of opportunities to practice it.
So yes, it makes me crazy when this profession gets reduced to “she’s friendly and organized.”
Because this is a real fucking job.
And I’m Retiring One Complaint
Executives, you are officially no longer allowed to tell me: “None of my Executive Assistants ever work out.”
Not until we examine who you actually hired.
If you hired:
Your friend’s sister’s co-worker who really wants to do this work…
A former inventory manager who hasn’t supported an executive but sure knows how to stack boxes in order…
The bestie you adore who has never worked in a corporate environment but loves going to the Container Store…
Or a musician who has never been an Executive Assistant…
Then perhaps Executive Assistants are not the problem. Perhaps you have never actually hired one.
A square peg is not defective because it doesn’t fit into a round hole.