Remote assistant onboarding checklist

The week before the start

• Send the signed agreement and confirm the start date, hours and payment date in writing.
• Create a work email address for the assistant instead of sharing yours.
• Set up a password manager with a shared vault for the accounts they need, so passwords are never sent in chat or email.
• Prepare delegated access: calendar delegation, inbox delegation or shared labels, a shared drive folder. Delegation can be removed in one click; a shared login cannot.
• Write a one-page “how I work” note: your priorities this quarter, who gets an instant reply, your meeting rules, how you like updates.
• List five real starter tasks with clear outcomes.
• Book the day-one call and a daily 15-minute check-in for the first two weeks.

Access: least privilege, written down

Give the access each task needs, not everything at once. Start with the calendar, a shared inbox label and the document folders, and add finance or customer data later, once trust is built and the need is clear.

• Turn on two-factor authentication on every account the assistant uses, with their own device.
• Keep a simple access list: tool, level of access, date given. You will need it at reviews and if the person ever leaves.
• Agree where documents live (a shared drive, not personal folders) and that work happens on work accounts only.
• If you handle personal data of customers in the EU, check your data protection obligations before you give access; this is general information, not legal advice.

Tools to set up

Keep the stack small. An assistant needs a place to talk, a place to track tasks, a place for documents and a way to share passwords:

• Chat: Slack or Teams, with one channel or thread for your daily exchange.
• Tasks: one shared list in Notion, Asana, ClickUp, Trello or Todoist that both of you open every day.
• Documents: Google Workspace or Microsoft 365, with a folder structure you agree on.
• Passwords: a password manager with sharing.
• Calls: the video tool you already use, plus a recording tool if you want to explain processes once and reuse the video.

Days 1 to 5: learn the way you work

1. Day 1. A long call: walk through the “how I work” note, the tools and the first tasks. The assistant checks that every access works before the call ends.
2. Day 2. The assistant takes over calendar scheduling with your approval on each booking.
3. Day 3. Inbox triage: they sort, flag and draft; you review the drafts.
4. Day 4. The first starter tasks are done; they write down each process they learn.
5. Day 5. Review the week: what worked, what to change, what they can now do without approval.

Days 6 to 10: hand over ownership

1. Day 6. Scheduling without approval, within the rules you agreed.
2. Day 7. Routine emails sent in your name; you read a sample at the end of the day.
3. Day 8. The first recurring process documented by the assistant, such as expenses or travel booking.
4. Day 9. A small project with a deadline, so you see how they plan.
5. Day 10. A longer review and a written list of goals for the first 30 days.

From here, the first 90 days guide covers the rhythm of the following months, and the trial period guide covers the checkpoints and the decision.

Common onboarding mistakes

• Sharing your own login instead of delegated access.
• Waiting for the assistant to “find work” in week one.
• Feedback only when something goes wrong.
• Changing priorities daily without saying why.
• Giving every access on day one and losing track of it.

If you hired through Silkstaff and the match does not work despite a good onboarding, tell us early. Silkstaff replaces the person free of charge if they leave or do not work out within 180^[1] days of the start date: one replacement per placement, once the placement fee has been paid and as long as the role, hours and pay stay as agreed. The fee itself is not refunded.