Why Good Executive Assistants Are Hard To Find (And How To Find One)

Key Takeaways

• The common complaints are flakiness, poor time management, needing too much direction, and weak communication.

• Most of these come from hiring on résumé and interview alone, and from unclear expectations after the hire.

• The fix is testing before hiring and structure after hiring.

• The global pool of experienced remote executive assistants is far deeper than any local market.

The Complaints Executives Repeat

Talk to ten executives about assistants and you hear the same four things. The assistant was unreliable. They could not manage their own time, let alone mine. They needed instructions for everything. Their communication was vague. Each of these is real. Each also has a cause that is easier to fix than most people think.

Cause 1: Hiring On Résumé And Interview Alone

Executive support is about judgment and follow-through, and neither shows up on a résumé. A confident interviewee can still be disorganized. The only reliable predictor is a test: draft three emails in my voice, sort these ten requests, tell me what you would do when three things go wrong at once. Our guide on executive assistant skills gives the tests.

Cause 2: A Shallow Local Pool

In any one city, the number of experienced executive assistants looking for work at a given moment is small. Executives end up choosing the best of three. The remote pool across Latin America, the Philippines, and South Africa is many times larger and includes people with years of US executive support experience, starting at $6/hr.

Cause 3: No Structure After The Hire

An assistant who seems to need constant direction often has an executive who never wrote anything down. Calendar rules, inbox rules, what to decide alone and what to escalate. Without them, asking is the only safe option. Our guide on setting expectations shows the one-page version.

Cause 4: No Rhythm

Vague communication is usually a symptom of no fixed rhythm. A daily preview, a weekly planning session, and a monthly review give the assistant a structure to communicate inside. See how an executive assistant should manage your calendar for the daily and weekly pieces.

How To Find A Good One

1. Write your working style and the outcomes you expect in 90 days.

2. Recruit from the global pool, not one city.

3. Test judgment and writing before any interview.

4. Interview for fit with scenario questions.

5. Check references on reliability and discretion.

6. Start with written rules and a fixed rhythm from day one.

That process is what a managed service does for you. We recruit executive assistants in all three regions, test them, and introduce a shortlist. See how it works.

The Part Only You Can Do

Even the best assistant fails with an executive who will not delegate, changes rules without saying so, or never gives feedback. Decide that you will hand over real authority, honor the rules you set, and hold the weekly session. Read delegation mistakes business owners make for the traps.

What This Looks Like In Practice

A managing partner at a consulting firm has been through three assistants in two years. Each interviewed well. Each faded within months: missed follow-ups, vague updates, constant questions. He assumes good assistants no longer exist.

Before the fourth search he writes his working style and his calendar rules on one page. He tests candidates with real emails and a priority-sorting exercise. He recruits remotely and hires an assistant in South Africa with seven years supporting executives at a bank. She starts with the written rules, sends a daily preview from day three, and runs the weekly planning session by week two. A year later he says she is the best assistant he has had. The pool was never the problem. The process was.

A Quick Checklist Before You Start

• Your working style and 90-day outcomes, written down.

• A writing test and a judgment exercise ready to send.

• Scenario questions for the interview.

• Reference questions about reliability and discretion.

• One-page rules for calendar, inbox, and escalation.

• A daily preview and weekly session in place from day one.

Good executive assistants are not hard to find. They are hard to find without a process.

Questions For A Reference Call

• Did they ever miss a deadline without warning you first?

• How did they handle a change of plans on short notice?

• What did they do when they did not understand an instruction?

• Would you trust them with confidential information again?

• Would you hire them again, and why?

Five minutes with a former manager answers most of what an interview cannot.

Questions Owners Ask

How Long Should I Give A New Executive Assistant?

Sixty to ninety days with clear rules and a weekly session. Judge on outcomes at 30 and 60 days, and act early if the fit is wrong.

Is A Remote Executive Assistant As Effective As A Local One?

For calendar, inbox, travel, and communication, yes. The only difference is physical errands, which are rarely the core of the role today.

What If My Last Assistant Was Great And I Just Cannot Replace Them?

Write down what made them great in terms of habits, then test for those habits. Great assistants are rare locally and common in the global pool.