Questions to ask when hiring an executive assistant

Ask about real situations, not strengths: how they sorted an inbox, handled a scheduling clash, kept a confidence, said no for a boss. Then pay for a short trial task. The trial shows you how they work, which the interview can only describe.

What you are testing

An executive assistant needs five things. Every question below tests at least one.

1. Judgment: knowing what matters, and what can wait.
2. Discretion: keeping confidential information confidential.
3. Writing: clear, short, in the right tone.
4. Systems: a way of keeping track that does not depend on memory.
5. Initiative: spotting problems before you do.

Interview questions

Judgment

• Walk me through how you would sort my inbox on your first day.
• Two important people want the same hour on my calendar. How do you decide?
• Tell me about a time you made a call without asking your boss. What happened?
• What would you never decide without asking me?

Discretion

• Tell me about a time you handled confidential information. What did you do to protect it?
• A team member asks you what I think of their work. What do you say?

Listen to how they talk about past employers. If they share private details about a former boss, they may share yours too.

Writing and tone

• How do you learn to write in someone else's voice?
• Show me an email you wrote that you are proud of. Why does it work?
• How would you decline a meeting request from a client I like but have no time for?

Systems

• What tools do you use to track tasks, follow-ups and deadlines?
• How do you make sure nothing falls through when you are out sick?
• How do you hand over your work when you go on leave?

Initiative

• Tell me about a problem you caught before your boss noticed it.
• What did you change in the way your last boss worked? Why?
• What do you need from me to do this job well?

Working style

• How do you prefer to get feedback?
• How often do you want to check in with me?
• What kind of boss have you found hard to work with?

The paid trial task

Give the top two or three candidates the same short task. Keep it to about two hours, and pay for it at the rate you would pay in the role. As a reference, the BLS median wage for executive assistants is $36.82 an hour in the US, per BLS data on O*NET for May 2025. Experienced freelancers on Upwork charge $38 to $50 or more an hour, per Upwork's rate page, as of October 2026.

Use made-up data. Never share real client emails or personal details with a candidate.

Good trial tasks:

• Inbox sort. Send 20 sample emails. Ask them to sort each into needs you, they answer, waiting or archive, and draft replies to three.
• Calendar puzzle. Give a messy week with clashes and new requests. Ask them to rebuild it with your rules, and list what they would ask you.
• Trip plan. A two-day trip with three meetings in another city. Ask for one itinerary document.
• Meeting brief. Name a public company and a meeting goal. Ask for a one-page brief.

What to look for: did they follow your rules, ask good questions, write clearly, and spot the thing you hid in the task? Put one trap in each test, such as a meeting that clashes with a focus block, or an email that sounds routine but is urgent.

Red flags

• Answers with no real examples, only general claims.
• Shares confidential details about a past employer.
• Typos or careless writing in the application or the trial.
• No questions about your priorities or how you work.
• Asks you to send passwords by email or chat.
• Cannot name the tools they use to track work.
• Blames every past problem on a former boss.
• Takes much longer than the trial time and does not say so.

Check references with specific questions

Ask past managers questions they cannot answer with yes:

• What did you trust them to handle without checking?
• Tell me about a mistake they made and how they handled it.
• What did you have to explain more than once?
• Would you hire them again for the same role?

The template

Candidate: [Name] Date: [Date]

Judgment

1. Walk me through how you would sort my inbox on day one.
2. Two important people want the same hour. How do you decide?
3. Tell me about a call you made without asking. What happened?

Discretion 4. Tell me about handling confidential information. 5. A team member asks what I think of their work. What do you say?

Writing 6. How do you learn someone else's voice? 7. How would you decline a meeting from a client I like?

Systems 8. What tools do you use to track follow-ups? 9. How does nothing fall through when you are out?

Initiative 10. Tell me about a problem you caught before your boss did. 11. What do you need from me to do this well?

Paid trial: [Task], [hours], [pay], due [date]

Score each area from 1 to 5:

• Judgment: [score]
• Discretion: [score]
• Writing: [score]
• Systems: [score]
• Initiative: [score]

Red flags noted: [Notes]

Reference check done: [Yes or no, notes]

Next steps

For general interview structure, see interview questions to ask candidates. Write the role clearly first with how to write a job description, and plan the first weeks with the onboarding checklist. If this is your first hire, how to hire your first employee covers the paperwork. Employment rules differ by state and country, so check with an employment lawyer on trial work and contracts.