How to Run a First Week With a New Remote Executive Assistant

Part of our guide: How to hire an offshore executive assistant

The first week decides whether a remote executive assistant becomes indispensable or stays a task-taker. Here's a day-by-day plan we use. It belongs to our offshore EA hiring guide.

Day 1: access and context

Set up named accounts with the minimum permissions they need, MFA and a password manager. Spend 30 minutes on a live call explaining your priorities this quarter, the people who matter most, and how you like to communicate. Share a short "how I work" note: response times, meeting preferences and pet peeves.

Day 2: shadowing

Let them watch your inbox and calendar (delegated access, not your password). Ask them to write down every recurring pattern they notice: which senders always need replies, which meetings always need prep.

Day 3: first owned workflow

Hand over one complete workflow, usually calendar scheduling. They propose times and draft invites; you approve. Agree a template for scheduling emails so their messages sound like your office.

Day 4: inbox rules

Agree labels (for example Action, Waiting, FYI, Read later) and what they can answer on your behalf. Start with low-risk categories such as scheduling requests and vendor confirmations.

Day 5: review and expand

Hold a 30-minute review. What worked, what was unclear, what they should take next week. Ask what they'd change about your process; good assistants will have ideas.

What should you avoid in week one?

• Handing over everything at once.
• Sharing your personal passwords.
• Giving vague feedback. Be specific: "Put agenda links in the invite body, not as attachments."

How do you know week one went well?

By Friday the assistant should own scheduling with light review, have drafted at least three checklists, and know your top priorities. Use our weekly check-in template from week two on.