How to Hire an Executive Assistant: The Complete Guide
When to hire, what to pay, how to screen for judgement rather than skills, and the onboarding sequence that decides whether it works.
Most founders hire their first executive assistant about a year later than they should, and then get it wrong on the first attempt. This guide covers the whole sequence: knowing when, deciding on a model, screening properly, and onboarding in the order that actually works.
It is written from the operator side. Our founders, Sarosh Farid and Ahmad Virk, spent five years as executive assistants and private operations managers before building this company, and most of what follows is what that job teaches you about why these hires fail.
When to hire
The usual signal is not workload. It is bottleneck.
You are ready when decisions are waiting on you to reply, when you are the reason things stall, or when more than a day a week disappears into scheduling, inbox and travel. If you are choosing between two meetings because you did not have time to look at the calendar properly, you passed the threshold some time ago.
The signs, concretely:
- You spend more time organising your calendar than deciding what should be on it
- Follow-ups stall because you are the only person who can move them
- You are hard to reach, and your team has started working around you
- You are permanently reactive — responding rather than choosing
- Every function in the business still reports to you
Choose the model before you choose the person
There are three, and picking the wrong one is the most expensive mistake at this stage.
Direct hire. You recruit, employ and manage. Cheapest over three years, most demanding of your time. Right if you already have someone who manages people well.
Placement. Someone else sources and vets; you hire and manage. A one-time fee, typically from 20% of first-year compensation. Right if you want them on your own team but do not have forty hours to screen candidates.
Managed support. A provider recruits, employs, trains and manages; you delegate work. $1,500 to $4,000 a month. Right if you want the output without acquiring another direct report.
We cover the cost side of this in detail in the cost guide.
Screen for judgement, not skills
This is the single most common failure. People screen against a checklist — calendar, email, travel, CRM — and every serious candidate passes it. Then the hire fails anyway, because the checklist never tested the thing that actually matters.
What to test instead. Give a scenario with deliberately incomplete information and watch the reasoning. “I am flying to Chicago Thursday for a 2pm. The flight is cancelled at 6am. What do you do, and what do you tell me?” A weak candidate asks what you would like them to do. A strong one rebooks, checks whether the meeting can move, flags the two things they could not resolve, and sends one message rather than six.
What else to test:
- Writing. Ask for a reply to a difficult email. Tone is the hardest thing to teach and the easiest to test.
- Prioritisation. Give six competing tasks and ask for an order plus a one-line reason each.
- Escalation judgement. Ask what they would interrupt you for and what they would not. The answer reveals how they think about your attention.
References matter more than interviews here. Ask a previous manager one question: “What did they handle that you never had to think about?” The silence or the specificity tells you everything.
Onboarding decides the outcome
A good assistant with poor onboarding underperforms a mediocre one with a proper ramp. The work happens before day one.
Before they start. Write a playbook: your working hours and how you like to be contacted, calendar rules (buffers, no-meeting blocks, which meetings can move), inbox conventions, the people who always get a fast reply, and the decisions they can make without asking. That last section is the important one and almost nobody writes it.
Week one. Access and tools. Shadowing rather than doing. They should be reading your inbox before they answer any of it.
Weeks two to four. Calendar first, always. It has explicit rules and cheap mistakes, which makes it the right place to build confidence in both directions.
Weeks four to eight. Inbox triage, then drafting for your approval. Sending unsupervised comes when the voice is right, not on a date.
Weeks eight to twelve. Travel, projects, follow-through. By the end of the quarter they should be surfacing things you had not thought about.
The full sequence is in the delegation guide.
The first ninety days, measured
You should be able to answer these at day 90:
- How many hours a week has this returned? (Four to six from calendar control alone is normal.)
- What has stopped landing on my desk entirely?
- What did they handle that I did not know about until afterwards — and was it handled well?
- Am I managing them more or less than a month ago?
If the last answer is more, something is wrong with the setup rather than the person.
Common mistakes
Hiring the cheapest option. There is a direct relationship between pay and retention. A $3-an-hour assistant is not a bargain; they are a churn event with a lead time.
Delegating outcomes before tasks. Nobody can own a result on week one. They can own a task on week one and an outcome on month three.
Never writing anything down. If the only copy of your preferences is in your head, you will re-explain them every time somebody leaves.
Not meeting the person first. If a provider will not let you meet the assistant before you commit, that is not efficiency. That is a roster allocation.