“I need to know everything about you. I need to know what you like, what you don’t like, how you work, how you prioritize your things, what I can remove from your plate, what I can delegate to other team members, how I can make your life easier. Because if I know you and I know how you think, I can start acting and resolving things on your behalf.”
We’ve overseen thousands of hires and placed candidates from 35+ countries.
I’ve had four Executive Assistants myself.
And that candidate I quoted above — she described it better than I ever could have.
An Executive Assistant doesn’t just work for you. They are trying to be you.
They learn how you think, what you avoid, what stresses you out, what you forget — and they build a system around your brain so you can focus on the work only you can do.
Think about that for a second.
The person in this role will know your spouse’s birthday, your barber’s schedule, your hotel preferences, your spending habits, your bank statements and exactly how much you spend on golf, the name of the client who annoys you, and the team member you’re about to have a hard conversation with.
They will know more about the texture of your daily life than almost anyone else in it.
(Very possibly they will be more in-tune with you and your emotions than your spouse. Let that sink in.)
And almost everything you’ll read about how to hire one is going to set you up to fail.
Here’s the thing:
I’ve watched this hire go wrong every which way, including my own. Remember…I’ve been through 4 Executive Assistants.
I’m difficult.
I’m intense.
I’m the founder who made every mistake on this list.
These are the 12 mistakes. Every single one is preventable. Most are invisible until it’s too late.
1. You Don’t Actually Know What You Need
“What percentage of the role is personal versus business?”
I’ve heard it hundreds of times. And every time a candidate asks it, it’s almost a disqualifier.
Here’s why:
From thousands of discovery calls with founders and business owners, the answer is the same roughly 90% of the time. They don’t want someone who handles personal stuff OR business stuff.
They want someone who figures things out — no matter the domain.
Monday morning it’s rescheduling a flight for a client trip. Monday afternoon it’s finding a birthday present for their wife. Tuesday it’s chasing down a vendor who ghosted on an invoice. Wednesday it’s sitting in a team meeting and flagging that a key hire hasn’t responded in four days.
There are no rules. There are no percentages. The first sentence in my EA SOP says it all:
The real title of this job is “problem solver.”
Think about Joan Holloway from Mad Men. She didn’t take orders. She ran the agency. She knew which clients were about to leave before the partners did. She managed up, down, and sideways simultaneously. The one time they tried to reduce her role, the entire office fell apart.
That’s the aspiration. And it starts with understanding that you’re not hiring someone to “manage your calendar.”
You’re hiring someone to manage YOU.
2. You Say You Want To Hire An Executive Assistant Who Takes Charge…But You Don’t Mean It
Everyone says the same thing on the discovery call:
“I want someone proactive. Someone who drives things forward. Someone who doesn’t wait to be told.”
And the founder picks someone soft. Someone who won’t challenge them.
I interviewed a Chief of Staff candidate once who put it perfectly. She said: “You all say you want someone to push back, but not really.”
She wasn’t being cynical. She’d lived it with multiple founders.
Here’s what actually happens:
You’re the founder. You built the ship. You’ve been in charge of every decision for years. And now someone walks in and starts making decisions without asking you first. Or worse — pushes back on one of your ideas and tells you it’s wrong.
It doesn’t feel like partnership. It feels like losing control.
And now what?
The Executive Assistants who last the longest — the ones who become truly indispensable — are the ones who push. Respectfully. Strategically. But they push. They tell you the schedule is insane. They tell you the hire you’re about to make is wrong.
They tell you to stop checking Slack at 10pm and for heaven’s sake, please eat a damn meal that doesn’t come from Uber.
The ones who just say “yes” to everything?
They usually don’t last.
You don’t have to be comfortable with it. You have to be ready for it.
There’s a difference.
3. You Were Intimidated by the Right Person
This is the one nobody talks about.
I had two finalists for my own Executive Assistant position. One of them — that Portuguese woman from the opening — asked about my past EA failures in the first fifteen minutes. She studied my company before the call. She told me the color-coding on my calendar was good but my meeting stacking left no room to breathe. She described exactly how she’d integrate herself into my life and business without a single hesitation.
The other had better chemistry. Easier to talk to. More comfortable.
I hired the comfortable one.
A few months later, when I needed someone to drive a complex visa process across two countries, chase down a government agency for a 23-day-old criminal background check, and manage a team that wasn’t performing — she couldn’t do it. She was an incredible Admin. She just couldn’t operate at the level the job actually required.
The candidate I passed on?
Well, I’ll never know. But I have my suspicions.
I passed on her because she was a little intimidating.
Here’s the lesson, and I mean this:
If you interview an Executive Assistant and you’re not at least a little bit uncomfortable — a little bit like, “damn, this person might be sharper than me in certain areas” — you probably haven’t found the right one yet.
The right EA should feel like hiring a business partner who happens to manage your inbox. Not an employee who follows instructions well.
4. You Think You Don’t Need One Yet
A business, like a plant, is either growing or dying.
There is no in-between.
If your business is not growing as a direct result of you not having enough time — if you’re the bottleneck in your own company — then the business is dying.
Slowly.
Quietly.
But…dying.
You’re doing your own scheduling. You’re chasing down vendors. You’re booking your own flights. You’re responding to emails that someone else could handle. You’re spending two hours a day on work that generates zero revenue and drains the energy you need for the stuff that actually moves the needle.
And every month you tell yourself: “I’ll hire someone when things calm down.”
Things don’t calm down. They compound.
Inbox Zero is a myth because it means you responded to all emails that needed it. What do you think that does? Oh yeah. You get more responses to your responses. You are punished for doing good.
Let that sink in.
The admin piles up. The strategic work gets pushed. The business grows at half the rate it should — if it grows at all.
The founders I talk to who made this hire early are almost always glad they did. The ones who waited are almost always kicking themselves for not doing it sooner.
5. You Hired An Executive Assistant For Tasks, Not Thinking
I had an Executive Assistant once who turned a simple task — have coffee and croissants at the office by 9 AM for a meeting — into a three-week saga spread across four sync calls.
First it was, “savory or sweet?” A week after the task was assigned. Not the same day.
Then it was, “coffee places in Poland don’t sell jugs.”
Then, “what kind of coffee?”
Then, “I’ll just order twelve Americanos and bring them up.” Then she realized she couldn’t carry them all. Then she asked if I could buy water and carry it upstairs.
Then she had the idea to bring her coffee machine from home with capsules. Then I had to entertain questions about which flavors. What intensity. What kind of cups to buy.
The task was: food and coffee at 9am. That’s it.
Know what the problem was?
The job description said “scheduling, email management, travel booking.”
- It attracted someone who executes instructions.
- Not someone who solves problems.
When you write a job description full of tasks, you get a task-doer. And a task-doer will…do tasks. Tasks are clear. Tasks have a call. Tasks are not ambigious.
And almost every one of you wants someone to solve ambiguous shit when you go to hire an Executive Assistant.
The person you actually need reads “food and coffee at 9 AM” and makes it happen. You walk in and it’s there. You never hear about it.
That’s the difference between an Executive Assistant and an Admin or a Virtual Assistant with a nice title.
6. You Chose Vibes Over Ability
Chemistry matters. I’m not going to pretend it doesn’t. You’re spending more time with this person than almost anyone outside your family. If you don’t get along, it won’t work.
But chemistry without capability is an expensive friendship.
The person I hired had incredible chemistry. We laughed on calls. She understood my humor. She was empathetic when things were stressful.
And when the hard stuff came — the cross-border paperwork, the team accountability conversations, the bookkeeper who couldn’t communicate — she couldn’t drive any of it forward. She would send me updates like, “here’s an email from the accountant.”
Cool, so…I still have to respond, and handle it, but now I feel like I’m being nagged. What’s the point?
No draft response.
No proposed solution.
No “here’s what I think we should do.”
Just… here’s the problem. Back to you.
I call that a boomerang. The task goes out, hits a wall, and comes right back to your desk. And it doesn’t matter how much you like someone if every hard task boomerangs.
7. You Tried To Hire An Executive Assistant…As Cheaply As Possibly
I see this pattern constantly.
Founder hires a VA from a marketplace for $5-10 an hour. The VA is responsive, friendly, and completely overwhelmed by anything that requires judgment. They forget things. They need everything spelled out. They can’t adapt when the situation changes.
So the founder fires them and hires another one. Same price. Same result.
After two or three rounds of this, the founder is convinced: “Virtual Assistants don’t work. I’ve tried.”
No, you haven’t.
You’ve tried hiring someone at the price of a fast food meal per hour and expecting them to operate like a Chief of Staff. That was never going to work.
The difference between a $300-a-month VA and a $3,000-a-month Executive Assistant is not 10x the cost. It’s a completely different human being doing a completely different job.
The VA follows instructions. The EA makes decisions.
The VA waits to be told. The EA tells you what needs to happen.
The VA asks twelve clarifying questions about a hotel booking you thought was obvious.
You get what you pay for. In everything.
People who understand this save years of their life.
8. You Hired In-Person for the Wrong Reasons
I made this mistake myself.
I wanted someone local. In-person. Someone who could come to the office, handle things face-to-face, translate when I needed help, run the occasional errand.
So I hired locally. The talent pool in my city was thin. I picked the best out of a mid field.
We started meeting three days a week. Then it became two. Then one.
And then I realized the proximity was actually creating a new problem. She had instant access to me.
She could interrupt anytime. Every small question became a hallway conversation instead of a structured message I could address on my own schedule.
Here’s the question to ask yourself:
What specifically requires physical presence?
If the answer is “occasional errands and translating” — that’s not a reason to limit your talent pool to a 30-mile radius. That’s a reason to hire the best person regardless of location and figure out the errands separately.
(Like telling your new remote EA to hire someone locally by the hour to handle errands.)
Remote Executive Assistants work across time zones, manage inboxes from different continents, and coordinate travel they’ll never take themselves.
The tools exist.
The question isn’t whether remote works.
The question is whether you’re willing to let go of the comfort of having someone down the hall.
9. You’re Expecting 1 EA to Be Everything
This one’s a trap that’s invisible until you’re in it.
People search for “Executive Assistant” when what they actually want is a Chief of Staff. Or an Operations Manager. Or a Project Manager who also handles their calendar.
The role has expanded so far beyond its original scope that the title itself is almost misleading.
Today’s best Executive Assistants understand business well enough to write SOPs, hold team members accountable, manage vendor relationships, and translate a founder’s scattered ideas into structured plans.
A lot of people just want the chaos to be pulled out of their noggin and organized.
What I actually needed wasn’t someone to book my flights and manage my email.
I needed someone who could look at my recruiting team’s performance data, identify that one person was sending 20x the messages as others to get the same result, and say — this is the problem, here’s how we fix it.
That’s an operational thinker.
Not a calendar-manager.
Not every Executive Assistant can do this.
And not every business needs this.
If you need someone to manage scheduling, travel, and email and do it exceptionally well — that’s a real role and a valuable one.
But if you’re expecting one person to also build your SOPs, manage your team’s performance, handle your finances, and drive your visa process, and handle your tax returns… you need to be honest about what you’re actually hiring for.
And you need to find someone screened for that level of work — which is exactly what we do.
10. You Gave Them Zero Framework
I once gave my EA a task: Book the Westin Hotel in Warsaw. I gave her the exact hotel name. The exact dates. Which nights to use the free certificate. Which nights to pay cash. I even logged into the Marriott account myself and confirmed the free night was available.
She booked the Sheraton.
When I asked what happened, she said she thought “Westin” meant the west side of the hotel. She had never heard of the Westin as a hotel brand. Instead of Googling “Westin Warsaw” — a three-second search — she guessed.
Now.
Was that a bad EA? Probably.
But here’s the part I had to own:
Most executives give 90% less context than they think they do. I happened to give very clear instructions on that particular task. But on plenty of others? I said “handle it” and expected mind-reading.
The boomerang problem — where every task comes back to your desk with more questions than answers — isn’t always the EA’s fault. Sometimes it’s because you never defined what “done” looks like.
I now use something called a Definition of Done for every task.
One sentence that describes the end state.
- “Three reservations at the Westin Warsaw are confirmed.”
- “Flight options with prices are in my inbox by 3pm.”
- “The vendor has been contacted and a follow-up is scheduled.”
Takes ten seconds to write.
And if something is unclear? The right EA asks one precise clarifying question. They don’t guess. They don’t assume.
…and they definitely don’t invent a hotel you never mentioned.
11. You Complimented Them Out of the Role
My first Executive Assistant was great. Driven, resourceful, a problem-solver. She wasn’t perfect on the details — some small mistakes here and there — but she figured things out in a way that made my life tangibly easier.
One day, I told her I thought she was incredibly talented. That I could see her running a company. That she was capable of so much more.
Two weeks later, she told me she no longer wanted to be an Executive Assistant. She wanted to be a Business Manager.
And I had given her the opening.
Here’s the thing:
The best Executive Assistants are ambitious. They’re smart, they’re driven, and they’re fully aware that they could probably do more. That tension is actually what makes them great — the ambition fuels the initiative.
But if you tell them they’re too good for the role, they’ll believe you. And then you lose the best person you had.
The right move? Channel the ambition. Give them projects. Give them ownership over systems and processes. Let them grow within the role.
Never frame the role as a stepping stone to something better. Frame it as the destination — the role that touches everything in the business and gives them more influence than almost any other position in the company.
Because that’s the truth. A great EA has more influence over the daily reality of the business than most Directors.
12. You Forgot About the Rest of the Team
I had an Executive Assistant who was excellent at her job. Detail-oriented, organized, protective of my time. Every metric you’d use to evaluate an EA, she scored well.
But she didn’t get along with my Ops Manager.
It started small. Tension over who had access to what. Friction over how information flowed. My EA thought the Operations Manager was incompetent.
In hindsight, she was right about that.
But she couldn’t build the case.
She couldn’t say, “Here’s the data, here’s the pattern, here’s why this person needs to go.”
Instead it became vague complaints.
“Things aren’t going well.”
“She’s not performing.”
And eventually it became: Me or her.
That’s the position you never want to be in. Because you lose someone either way.
Here’s what I do now:
Before making the EA hire, I have them meet key team members. Not an interview — a conversation. I want to see how they interact with the people they’ll be working alongside every day. I want to see if the Recruiter feels threatened. If the Account Manager gets defensive. If the EA candidate can navigate those dynamics with enough emotional intelligence to earn trust without stepping on toes.
And I bring my wife.
Not for every hire. But when I know the EA is going to be handling personal things — birthdays, family travel, spending habits, appointments — my wife should be comfortable with that person having that access.
This is an intimate hire. Treat it like one.
Brook Hiddink, CEO/Founder talks about his experience hiring an Executive Assistant through HireUA:
What It Looks Like When It Works
Everything above might make you think this hire is impossible.
It’s not. It’s just hard to get right. And when it’s right, it changes everything.
It’s the person who manages your inbox so well that you open your email and everything is sorted by priority — and the ones marked for your response already have a draft written that’s 90% there. You tweak two sentences and hit send.
Total time: 4 minutes for what used to take 1 hour.
It’s the person who reminds you that your wife’s birthday is in six days and a present should be in your hands a week before. Not because you asked. Because they have a system and your life is in it.
It’s the person who sits in your team meetings and builds a paper trail of every commitment, every deadline, every promise — so when someone tries to move the goalpost three weeks later, you pull up the recap and say, “That’s not what we agreed to.”
It’s the person who books your train ticket in an open compartment facing the direction of travel because they learned that backward motion and a screen gives you motion sickness. A detail you mentioned once, three months ago, in passing.
And it’s the person who, when the government agency loses your paperwork and the deadline is in nine days — doesn’t send you a message saying, “What should I do?”
They send you a message that says:
“Handled. Digital version sent via expedited courier. Confirmation attached. You don’t need to do anything.”
That’s the hire. And it doesn’t happen on day one. It happens at month six, month twelve, month eighteen.
It compounds…like a plant that was given the right soil and enough patience to grow.
The Access Problem Is Already Solved. The Trust Problem Isn’t.
One of the biggest hesitations I hear from founders: “How do I give them access to my finances? My passwords? My personal information?”
It’s really not hard.
Most major credit cards let you issue a virtual card with a spending limit. I just checked myself. Capital One, Amex, Chase. All allow some version of this. If you’re using ho-dunk-town small savings bank, don’t know what to tell you.
Add a virtual with a $300 cap. Review the expenses. Pay it off. If they hit the limit, it declines. Start there and raise it as trust builds.
Password access?
Use 1Password or any password manager with a vault system. Anything you want them to have goes in the EA vault. Anything you don’t stays out. Two minutes to set up.
Personal information like birthdays, preferences, dietary restrictions?
We live in a world where cameras are on every street corner. Your Instagram shows where you had dinner last Tuesday. Nothing is truly private anymore.
Does it really matter that your EA knows your wife’s birthday and reminds you to buy a present a week early?
No. What matters is whether you trust them.
And trust isn’t built by withholding access.
It’s built by giving access in stages and watching what they do with it.
Start with a $50 budget to solve a problem. See how they handle it.
Raise to $100. Then $300. Review. Adjust. Repeat.
One more thing:
Talk to your spouse before you make this hire.
Your EA is going to know intimate details about your family’s life. Travel schedules, spending habits, personal appointments, children’s school logistics. Your partner should be comfortable with that — and involved in the process.
I’ve brought my wife to meet EA candidates.
When you know the role bleeds into personal territory — and it almost always does — having your spouse in the room changes the dynamic. It makes the hire feel less like a business transaction and more like what it actually is.
Bringing someone into your inner circle.
How Our Process Works
We don’t post a job description and hope for the best.
When you book a call with us, we start by understanding how you work. Not what tasks you need handled — how you think, how you communicate, what drives you crazy, what your team looks like, and where the actual bottlenecks are.
From there, we source from our network of pre-screened global candidates. We test for judgment, not just skills — with an internal scoring system we’ve developed over the last half-decade.
We screen for the ability to operate independently, anticipate problems, and push back when something doesn’t make sense — because that’s what separates the hire that lasts from the one that flames out at month three.
Candidates in your inbox within 5 business days. One all-in monthly fee. Replacement guarantee built in. If it doesn’t work, we find someone else — on us.
Click Here to Start Hire an Executive Assistant
Frequently Asked Questions
How much does an Executive Assistant cost?
It depends on the level.
A task-focused VA might run $500-800/month. In the US, the same hire costs $60,000-120,000 per year.
What’s the difference between an Executive Assistant and a Virtual Assistant?
Judgment.
A Virtual Assistant follows instructions. An Executive Assistant makes decisions. The VA asks, “Should I book Hotel A or Hotel B?” The EA books Hotel A because she knows your loyalty program, your room preference, and your meeting location — and she’s already confirmed late checkout.
Can this be done remotely?
All of our placements are remote.
Slack, Google Workspace, 1Password, Zoom — the tools make it seamless. The question isn’t whether remote works. It’s whether you’re willing to trust someone you don’t see every day. If you are, your talent pool goes from your zip code to the entire world.
How long does onboarding take?
Expect a ramp.
Week one is learning your systems, preferences, and communication style. Month one is drafting emails for approval and managing calendar with guidance. Month three is operating at 80% autonomy. Month six is when they start anticipating. Don’t expect month-six performance on day one.
What skills should I look for?
Beyond organizational skills, the ones that matter most are judgment, discretion, and emotional intelligence.
Can they read a room? Can they handle sensitive information without being told it’s sensitive? Do they ask one clarifying question or seventeen?
Should I use a staffing agency or hire directly?
If you have time to post the role, screen 200 resumes, run four rounds of interviews, check references, design a trial task, and onboard — hire directly.
If you’d rather spend that time on the work that actually grows your business, that’s what we’re here for.
