How to Hire an Executive Assistant: Steps, Tests and Scorecard

To hire an executive assistant, start by tracking a week of your own time so you know exactly what you want to hand over. Then choose a hiring route, write a short brief, and test finalists with a paid task built from your real calendar and inbox. Interviews tell you who is pleasant. The test tells you who can run your day.

This guide covers each step of how to hire an executive assistant, with a work test you can copy, a scorecard, interview questions and a setup plan for the first week.

Not sure an EA is the right hire yet? Read what an executive assistant does, or compare the two assistant roles in executive assistant vs virtual assistant.

Step 1: Track a week of your own time

Before you write a job post, keep a simple log for five working days. Every time you do something that does not need your judgment, write it down with the minutes it took. Typical entries for a founder:

• Moving meetings and replying to scheduling emails
• Sorting the inbox and chasing replies
• Booking travel and filing expenses
• Preparing notes before calls and sending recaps after
• Reminding people about deadlines

At the end of the week, group the entries and add up the hours. This list does three jobs. It tells you whether you need a full-time EA or a few hours of help. It becomes the job brief. And it becomes the onboarding plan, because the first tasks you hand over are the ones that took the most time.

Step 2: Decide what kind of EA you need

"Executive assistant" covers very different jobs. Decide which one you are hiring for:

• Calendar and inbox EA. Owns scheduling, email triage and follow-ups. This is what most founders need first.
• Operations-leaning EA. Adds light project management, vendor coordination, invoicing and team reminders.
• Personal and travel EA. Handles travel, events and some personal logistics.

Also decide hours. An EA earns their keep by reacting during your day: a meeting moves, a client replies, a flight is delayed. If you need that cover, you need someone working your time zone, not someone who checks in twice a day.

Step 3: Choose how to hire

Route	Good for	Trade-off
Hire directly (LinkedIn, job boards)	Teams with time to screen and an HR process	Weeks of sourcing and screening, plus payroll and contracts
Recruiter or placement agency	Senior, on-site EAs for executives	A placement fee, and you still handle employment
Freelancer or assistant agency	A few hours a week of light admin	Often shared across clients, may not be the same person
Staffing partner, full-time and dedicated	A founder who needs one person on their day, every day	A monthly commitment

Each route has a different price structure. We compare them line by line in how much an executive assistant costs.

Step 4: Write a one-page brief

Keep it short. A good executive assistant job description has:

• The top five tasks, from your time log, in order of importance
• Your tools, such as Google Workspace or Microsoft 365, Slack, Notion, Calendly
• Your hours and time zone
• Your rules, for example "no meetings before 10am" or "investors always get a reply the same day"
• What good looks like after 30 days, for example "I no longer touch my calendar"

Write the post around a real day: "You start by triaging overnight email, then confirm today's meetings and send me a one-page plan." Candidates who like that day will apply.

Step 5: Run a paid work test

This is the most important step when hiring an executive assistant. Give your three or four finalists the same task, cap it at about two hours, and pay for their time.

The executive assistant skills test

Build it from your real work, with names and private details changed.

Part 1: The calendar puzzle. Share a week with 12 to 15 meetings, two conflicts, one meeting across time zones and a personal block. Ask them to fit in three new requests and explain what they moved and why.

Part 2: Inbox triage. Send 15 sample emails: a few urgent, a few that can wait, some newsletters, one that needs your decision and one that looks urgent but is not. Ask them to sort each into reply, delegate, schedule, archive or escalate, and draft two replies in your voice.

Part 3: A meeting brief. Name a real company you are meeting next week. Ask for a half-page brief: who you are meeting, what they do, recent news and two questions worth asking.

What to look for:

• Did they protect your rules, or just fill gaps?
• Did they ask a sensible question when something was unclear?
• Are the drafted replies short, polite and sendable as written?
• Did they flag the email that needed your decision?

You will learn more from these two hours than from three rounds of interviews.

Executive assistant scorecard (template)

Score each finalist from 1 to 5 after the test and the interview. Write what "good" means before you see any results.

What you are scoring	What a 5 looks like	What a 1 looks like
Judgment	Knows what to handle alone and what to escalate	Asks about everything, or decides things they should not
Written communication	Clear, short, matches your tone	Long, vague or overly formal
Accuracy	Right times, right time zones, right names	Small errors that you would have to catch
Discretion	Treats sample data carefully, asks about confidentiality	Casual with private details
Follow-through	Closes every loop and confirms when done	Leaves tasks half finished without saying so
Tool fluency	Comfortable in your calendar, email and notes tools	Needs hand-holding on basics

Weight judgment highest. Tools can be learned in a week. Knowing when to interrupt you cannot.

Executive assistant interview questions

Use the interview to test thinking, not to repeat the CV.

• "Two people I care about both need my only free hour this week. What do you do?" Look for a clear rule, such as asking which one is tied to revenue or a deadline, not a coin toss.
• "You see an email from an investor at 9pm and I am offline. What happens next?" Good answers depend on the content and mention your rules.
• "Tell me about a mistake you made with someone's calendar and how you fixed it." Everyone has one. Listen for ownership.
• "How do you keep track of follow-ups you promised on my behalf?" Look for a system, not "I remember."
• "What would you need from me in the first week?" Strong candidates ask for your preferences, priorities and key contacts.
• "Which tools have you used to manage an executive's day?" Experience with your stack shortens ramp time.

Red flags when hiring an EA

• No questions during the work test. Real calendars are messy. A good EA asks.
• Loose with confidential details from past bosses during the interview. They will be loose with yours.
• Wants your passwords rather than delegated access.
• Juggling several clients while applying for a full-time role. Your urgent request will wait behind theirs.

Step 6: Set up access safely

Do not share your password. Use the delegation features your tools already have. In Gmail, you can add a delegate who can read, send and delete email on your behalf without knowing your password or changing your account settings. Calendars can be shared with edit rights in the same way. Store any other logins in a password manager with a shared vault.

This keeps you in control. Every account stays yours, and you can remove access in one click if things change.

Step 7: Plan the first 30 days

• Week 1: Calendar first. They manage scheduling while you review each change. Share your rules and a list of key contacts.
• Week 2: Inbox triage. They sort and draft using a simple inbox triage system. You approve before anything is sent.
• Week 3: They send routine replies on their own and prepare meeting briefs.
• Week 4: Add travel, expenses and follow-ups. Agree a daily end-of-day summary and a short weekly check-in.

For the wider routine, see our guide to onboarding a remote employee in the first 30 days.

Hiring an executive assistant through Zenstack

Zenstack does steps 3 to 5 for you. On a 30-minute call you tell us what you want off your plate, your tools and your hours. Within 48 hours you meet a shortlist of experienced, already-vetted EAs, each with a 2-minute video introduction. You run your own work test if you like, and you choose.

Your full-time remote executive assistant works only for you, during your hours, inside your inbox, calendar and tools. Rates start at $12 an hour, about $1,920 a month full-time, with recruiting, contracts, payroll and weekly check-ins included. If the fit is wrong in the first 30 days, we replace them at no cost. See pricing to plan the budget, or tell us about your week and we will match you with an EA who has done that work before.