How to Hire an Executive Assistant: The 2026 Playbook

The Problem

You’ve decided the admin has to go to someone else. Three unresolved conflicts are sitting on the calendar. Forty threads are waiting on a decision from you, six of them today. Dinner needs booking, the hotel needs a call about a late checkout, an intro that went quiet needs chasing. Most of it doesn’t need you specifically - it needs someone. All of it is currently yours.

So you’re hiring an executive assistant. Right instinct, and also a real project, one most executives underestimate badly: six to ten weeks from writing the job description to a signed offer, another six to twelve before the person is operating independently, and a real chance the first hire isn’t the right fit, which puts you back at the start of both.

I’m Nir Sabato, co-founder of Catch. We build an AI executive assistant, an admin savior in our language, that handles this work end to end for leaders at US mid-market companies. I have a stake in how you answer this question, and I’d still rather hand you the actual hiring playbook than a pitch, because the executives who hire well are the ones who defined the job before they started looking. What follows is the whole process: scoping the role, the job description, where to find candidates, what to test in the interview, the trial task, what to pay, and the first 90 days. Then, at the end, a direct comparison against having an AI executive assistant handle the same work.

How to Hire an Executive Assistant: The Short Version

Seven steps, in order:

1. Log your admin for one week so you know what the job actually is.
2. Write a job description built on that log, not on a template.
3. Source candidates through referrals, placement firms, job boards, or a fractional hire.
4. Screen for judgment and writing in a 30-minute first call.
5. Run a paid trial task on real work before you make an offer.
6. Set pay against the fully loaded cost, not the base salary.
7. Run a structured first 90 days with a written preferences doc and a daily sync.

Skip step one and everything after it gets shakier. It’s also the step almost everyone skips.

Step 1: Define the Role Before You Write the Job Description

For one full week, log every administrative task you want off your plate. Write it down as it happens rather than reconstructing it on Friday afternoon, because estimates go wrong in a predictable direction: the memorable tasks get over-weighted and the constant small ones disappear.

Then sort the log into four buckets:

• Calendar and scheduling. Booking, rescheduling, conflict resolution, coordinating three-way meetings, protecting focus time.
• Email. Triage, drafting, replying, chasing threads that went quiet.
• Coordination and bookings. Reservations, calls to vendors and hotels, travel logistics, meeting prep and briefings.
• In-person and operational. Anything physical: office management, event setup, greeting a guest, collecting something, running the room.

Two things usually fall out of this exercise. The total is bigger than you expected. And the split is lopsided. For most executives the first three buckets swallow the log while the fourth sits close to empty. That ratio decides what kind of hire you should be making, and it’s probably the single most useful number the whole process will give you.

Step 2: Write a Job Description That Filters

A good executive assistant job description has one job: making the wrong candidates self-select out. Most don’t manage it, because they’re stitched together from generic templates and could describe any admin role at any company.

Include these:

• The real scope, drawn from your log, with rough proportions. “Roughly 50% calendar and scheduling, 30% inbox, 20% coordination and prep.”
• The decisions this person gets to make alone. Can they decline a meeting on your behalf? Move a standing 1:1? Reply to a client without checking first? Be specific. This is the part candidates most want to know and the part job posts most often skip.
• Working hours and reachability, stated plainly. If you need coverage until 7pm Eastern or occasional weekend responsiveness, put it in the post.
• Tools. Google Workspace or Microsoft 365, your CRM, your project tracker, your notetaker.
• Confidentiality. This person will see board material, compensation conversations, and legal threads.
• Pay range. Required in a growing number of states, and separately, the fastest way to stop wasting everyone’s time.

Leave out “other duties as assigned.” Strong EA candidates read that as “we haven’t defined this job,” and they’re usually right.

Step 3: Where to Find an Executive Assistant

Four realistic channels. They trade off on speed, cost, and how much of the work lands back on you.

Referrals from other executives. Highest yield by a wide margin. Ask peers, board members, and investors whose assistants they’d hire again, then ask those assistants who they’d recommend. Good EAs know other good EAs. It’s slow, it doesn’t scale, and it still produces the best candidates.

Executive assistant placement and staffing firms. They recruit, screen, and shortlist for you, and the specialist firms in this category understand the role well enough to filter properly. You pay for that as a placement fee, usually a percentage of first-year salary, or as an ongoing markup on a managed hire. Fastest route to a qualified shortlist if the budget is there.

Job boards and LinkedIn. Widest reach, most volume, most work. A well-written post for a mid-market EA role will pull a lot of applications, and the screening burden is entirely yours. Workable if you did step two properly. Painful if you didn’t.

A fractional or virtual hire. Part-time or contract support, often 10 to 20 hours a week, sourced through marketplaces or specialist services. Materially cheaper, faster to start, and the right call when the log says you need coverage rather than a full-time partner. The tradeoffs are context and continuity: someone working 15 hours a week across several executives will never know your business the way a dedicated hire does. Offshore hiring cuts the cost further, and it strains in three predictable places: time-zone overlap, US business context, and phone work where an American accent matters.

Step 4: What to Actually Test in the Interview

Run three stages, and keep the whole thing inside three weeks. Strong EA candidates are usually interviewing elsewhere, and a slow process loses them.

Stage one, 30 minutes, screening. Confirm scope fit, hours, comp expectations, and notice period, then ask them to walk you through a week in their last role in detail. Vague answers here are the reliable early signal.

Stage two, 45 minutes, judgment. This is the stage that matters. Skills are trainable and judgment mostly isn’t, so build your executive assistant interview questions out of scenarios from your actual week:

• Two people you can’t afford to offend want the same slot on Thursday. There’s one slot. What do you do?
• A client email lands sounding angry while I’m mid-flight and unreachable for four hours. Walk me through it.
• I’ve told you to protect Friday afternoons. My co-founder asks for Friday at 3pm. Now what?
• You catch a mistake in something I already sent. What happens next?

You’re listening for one thing: can this person tell the difference between what to handle, what to escalate, and what to leave alone? An assistant who escalates everything hasn’t reduced your load. An assistant who escalates nothing will eventually make a call you needed to make yourself.

Stage three, writing. Have them draft two replies in your voice from real (redacted) threads: one declining something politely, one chasing a client who’s gone quiet. Writing in someone else’s voice is the hardest part of the job and the easiest thing to test before you hire.

Then reference-check specifically for discretion. Not competence. Discretion. Ask former employers straight out whether they’d trust this person with compensation data and board material.

Step 5: The Paid Trial Task

Never hire an executive assistant without a paid trial. Two to four hours of real work, paid at a fair rate, run with your two finalists.

Give them something genuine:

• A three-way meeting that actually needs rescheduling, with a real conflict in it.
• One day of inbox triage: what needs you today, what can wait, what needs no reply at all.
• A restaurant booking with a constraint, or a call to a vendor to sort out a detail.
• A short pre-read for a meeting on your calendar tomorrow.

An interview tells you how someone talks about the work. A trial shows you how they do it, how they ask questions when the instructions are incomplete, and how they behave when something goes slightly sideways. It also tells you something about yourself, which is how clearly you can delegate. If briefing the trial was a struggle, briefing the hire will be too.

What to Pay an Executive Assistant in 2026

Base salary first, then the number that actually matters.

Public salary trackers put the 2026 US average for an executive assistant somewhere between roughly $64,000 and $89,000, depending on the source and methodology. The ranges are wide because the role is wide: metro, industry, seniority of the executive, and whether the job carries real operational scope all move the number substantially.

Option	Typical 2026 US pay	Fully loaded annual cost
Catch (AI, handles the traditional EA role)	$99/month flat	$1,188
Fractional / part-time EA (~20 hrs/wk)	$30 - $60/hour	~$31,000 - $62,000
Executive assistant, mid-market	$65,000 - $95,000 base	~$85,000 - $125,000
Senior EA to a CEO, major metro	$100,000 - $140,000 base	$120,000 - $180,000

Loaded cost is the number to budget against. Payroll taxes, benefits, equipment, software seats, recruiting fees, and your own management time add roughly 25 to 40% on top of base. A senior US executive assistant runs $120,000 to $180,000 a year all-in. Compare against that figure, not the base salary, and not the hourly rate.

While you’re at it, add the cost of the hire itself: your time writing the role and screening, a placement fee if you use a firm, and the ramp period where you’re paying full salary for partial output.

The First 90 Days

The first three months decide whether this works. Most EA hires that fail don’t fail on capability. They fail because nobody built the operating relationship.

1. Grant access deliberately, on day one. Calendar, inbox, and the tools they need, scoped to the job and no wider.
2. Write a preferences document. Meeting lengths and buffers, who always gets a slot and who never does, how you want emails to sound, what stays protected, when to interrupt you and when not to. Two pages. This is the highest-leverage hour you’ll spend.
3. Start supervised, then release. Weeks one to three: they draft before sending, propose before booking. Weeks four to eight: they act on the routine and escalate the rest. Week nine onward: they own the calendar.
4. Hold a 15-minute daily sync. Priorities, handoffs, anything left unclear from yesterday. Of everything on this list it’s the habit with the highest return, and it’s the first one executives drop.
5. Correct immediately and specifically. “Don’t book me back-to-back after a board call” in month one becomes a decision they make correctly without you in month three.
6. Run a 90-day review against the original task log. Which buckets actually moved off your plate? That’s the only scorecard that matters.

Do this properly and by month three you have someone who knows how you work and takes real weight off your week. That’s a genuinely valuable relationship, and worth the effort it takes to build.

The Alternative: Most of That Log Is Already Handled

Go back to the task log from step one and look at the first three buckets.

Calendar management and conflict resolution. Scheduling and coordinating multiple parties. Email triage, drafting, sending, and chasing the threads that went quiet. Reminders and meeting prep. Restaurant and hotel bookings. Calls to vendors and front desks. That’s the traditional executive-assistant role, and it’s what Catch does.

Not partially, and not as some lesser category of help. Catch resolves a calendar conflict by reaching out to the other party to reschedule it, not by flagging it for you. It triages the inbox, surfaces what needs you, and sends what you actually meant to say. Scheduling runs end to end, weighing your availability against the urgency of the request and booking the slot rather than handing the job back to you. When a shareable link is what you want, it builds one to your constraints in seconds. It books the restaurant, places the real outbound call to the hotel about the late checkout, sends the text message, updates HubSpot or Zoho when a deal moves, closes tasks and pulls briefs from Asana and Notion, and reminds you of the thing you’d have forgotten before you walk into the room. Travel booking is in beta.

You reach it in Slack, over email, by text message, on iMessage, or by picking up the phone and talking to it.

Three differences from a hire, stated plainly:

• Cost. $99/month, flat. No credits, no tiers, no per-call fees, voice included. Set that against $120,000 to $180,000 a year loaded.
• Time to value. Signup is self-serve and setup takes under three minutes: connect Gmail or Outlook, then hand over a real task. Set that against six to ten weeks of hiring and another six to twelve of ramp.
• Availability. Around the clock, responding in seconds. A person has evenings, holidays, and time off, and should.

Catch applies judgment rather than running rules. It learns your priorities, your key relationships, your meeting preferences, and how you like things handled, picking that up from your connected calendar and inbox and from the corrections you give it. Early on it checks the details with you before doing things on your behalf. As it builds context it takes more on itself, and comes back to you when a decision genuinely needs you. That autonomy gets earned the same way you’d let a new hire earn it.

Catch handles executive-level information, and it’s built for that. It is SOC 2 Type II certified and a Google Verified app.

None of this is an argument for letting anyone go. I want to be precise about that. If you already have an assistant you value, what Catch takes over is the traditional admin load, which frees a capable person to move into operational and in-person work that genuinely needs a human: running the office, coordinating events, handling what happens in the room. Catch does not do physical or in-person work.

And if you haven’t hired yet, the question gets simpler. If your log is mostly calendar, inbox, scheduling, prep, and bookings, that work can be handled today for $99/month while you decide whether you still want to run a hiring process at all. Hire a person when you need presence in a room, judgment on the ground, or work that lives off the screen.

Who This Is For

• CEOs and founders at 30 to 200 person companies about to open an EA req
• VP Sales and VP Operations leaders whose calendar has become the bottleneck
• Partnerships, BizDev, and marketing leaders coordinating external scheduling all day
• Executives who’ve hired an EA before and watched the relationship stall under management overhead
• Startup founders carrying the whole admin load with no support in place

How It Works

1. Sign up. Self-serve, no demo required, 10-day free trial.
2. Connect Gmail or Outlook. Grant permissions, then add Slack, Asana, Notion, or your CRM if you use them.
3. Start talking to it. Text message, Slack, email, iMessage, or phone. Nothing to build, no workflows to configure.
4. Hand off a real task. A conflict to resolve, a day of inbox to triage, a dinner to book.
5. Let it learn you. It picks up your priorities and relationships, acts on its own once it has enough context, and asks when something is genuinely ambiguous.

Results You Can Expect

Executives using Catch have delegated more than 20,000 tasks, scheduled over 5,000 meetings, and handed off more than 200,000 emails. What that adds up to in a week is fairly plain: a calendar that resolves its own conflicts, an inbox that stops being the first and last thing you touch, and the small coordination jobs closed without you.

On cost, a flat $99/month sits against $85,000 to $125,000 loaded for a mid-market EA. On speed, three minutes of setup sits against three to five months from job post to independent operation.

Frequently Asked Questions

Get Started

If you’re about to hire an executive assistant, do step one first. Log a week of admin, sort it into the four buckets, and look at the split.

If most of it is calendar, inbox, scheduling, prep, and bookings, that work can be off your plate today. Connect Gmail or Outlook, start texting Catch, and hand it a real task. A week of the free trial will tell you what you’re actually hiring for.