20 interview questions for a remote executive assistant

How to use these questions

Pick eight to ten for a 45-minute call and ask the same ones to every finalist. Take notes against the “good answer” column, not against your overall impression: people who interview smoothly are not always the ones who manage a calendar best. Follow up with “what happened next?” and “what would you do differently?”; real examples hold up, invented ones get thin.

Do the call on video and in English for the whole time. It is the most reliable English check you have; our guide to checking English level explains what to listen for.

Calendar and inbox

1. Two senior people ask for the same slot with me. What do you do? Good: checks priorities you have set, offers alternatives to one of them politely, tells you what they did. Warning: asks you every time, or decides silently.
2. How do you organise an inbox you take over for the first time? Good: a few clear labels or folders, a daily triage routine, a list of what needs you. Warning: a complex system with no routine.
3. Tell me about a scheduling mistake you made. Good: owns it, fixed it, changed a habit (for example always writing the time zone in invites). Warning: “I don't make mistakes”.
4. How do you handle meetings across three time zones? Good: uses a tool, writes both times in the invite, checks daylight-saving changes. Warning: does the maths in their head.
5. Which emails would you answer without asking me? Good: a clear line, such as scheduling, receipts and routine requests, and asks you to confirm the line.

Priorities and judgement

1. It is 17:00, you have three urgent requests and time for one. How do you choose? Good: asks what each blocks, picks the one with the nearest deadline or highest stake, tells the others when they will get an answer.
2. When did you push back on a manager? Good: a specific case, respectful, with a reason and an alternative. Warning: never, or always.
3. What do you do when instructions are unclear? Good: asks one precise question, proposes a default, moves on. Warning: waits.
4. How do you keep track of follow-ups? Good: a list or a tool, checked daily, with dates. Warning: “I remember”.
5. Tell me about a time you noticed a problem before your manager did. This is the question that separates assistants who carry work from those who wait for it.

Written and spoken communication

1. Write a two-line reply declining a meeting on my behalf. Ask them to type it in the chat. Good: polite, short, offers an alternative.
2. How do you update a busy manager? Good: one daily message with done, waiting and decisions needed; urgent items separately.
3. How do you write to someone senior you have never met? Good: context first, one clear ask, easy to say yes to.
4. Tell me about a difficult conversation with a vendor or client. Good: calm, specific, a result. Listen also for how clearly they tell the story.

Tools and remote work

1. Which tools have you used daily, and for what? Good: specifics, such as “shared calendars in Google Workspace for four people”. Warning: a long list with no detail.
2. How do you work with a password manager and shared accounts? Good: knows not to share passwords in chat, understands delegated access.
3. What does your working day look like when your manager is asleep? Good: a plan for the async part of the day and a clear handover.
4. What do you need from me to do this job well? Good: specific asks, such as priorities, a weekly call and access. It also shows whether they have done the job before.
5. How do you protect confidential information working from home? Good: separate work accounts, screen lock, no shared devices, care with documents.
6. Why this role, and why remote? Listen for a real reason and realistic expectations about hours.

Score the answers, not the impression

Score each question from one to three straight after the call: one for vague or worrying, two for acceptable, three for specific and convincing. Add a separate score for English and one for the questions the candidate asked you. Compare finalists on the sheet, then give the best two a short paid test, which you can plan with our test task guide.

If you would rather receive candidates who have already passed a written task, a recorded voice answer and a live call, ask Silkstaff for a shortlist.