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What to hand an executive assistant first

The first month decides whether an assistant becomes indispensable or stays underused. Here's an order for handing work over that builds trust on both sides.

JiveTalent team

Many founders who hire an executive assistant have the same first week. There's a long list of things to hand over and no clear place to start. So they hand over a little, worry about the rest, and end up doing most of it themselves for another month.

The fix is to delegate in a deliberate order: start with work that's easy to check, then move to work that needs your judgment once you trust theirs. This guide sets out that order, what to keep for yourself, and how to share access without sharing your passwords.

  1. 1

    Before day one: look at two weeks of your time

    Before your assistant starts, spend 20 minutes going back through the last two weeks of your calendar and inbox. Write down every task that:

    That list is your first handoff plan. It's also the start of the role brief. If you haven't written one yet, our one-page hiring framework covers what to include.

    • repeats (weekly reports, invoice reminders, meeting scheduling)
    • follows a pattern you could explain in a few sentences
    • you put off because it's tedious, not because it's hard
  2. 2

    Week one: the calendar

    The calendar is the best place to start. Mistakes are visible and easy to fix, and handing it over gives you time back from the first day.

    Write a short page of calendar rules, for example:

    Then share your calendar with the right permission level. In Google Calendar you can let someone see event details, make changes, or make changes and manage sharing. An assistant running your calendar needs "make changes" from day one. "Manage sharing" can wait.

    • the hours you take meetings, and in which time zone
    • the days you keep free for focused work
    • how long a standard call is, and how much buffer goes between them
    • who gets priority (customers, investors, your team) and who should be offered a later slot
    • which meetings you always want to approve before they're booked
  3. 3

    Week two: meeting prep and follow-ups

    Once your assistant runs your calendar, the next step is to make your meetings better:

    This is where a good assistant starts to show judgment, and you'll see quickly whether their notes are useful. Give feedback on the first few, then let them settle into a format.

    • Before each external meeting: a short brief with who you're meeting, the context, the last email exchanged and what you want out of it.
    • After each meeting: a follow-up email drafted for your review, and action items added to your task list.
  4. 4

    Weeks three and four: the inbox

    The inbox is usually what founders want off their plate most, and it needs the most trust. So it comes after the calendar and meeting prep, not before.

    Start with triage, not replies. Ask your assistant to sort your inbox into a few clear buckets:

    After a couple of weeks of approving drafts, you'll know which kinds of reply you can let them send directly. Write those down as "send without asking" rules and add to the list as trust grows.

    1. 1

      For you to answer:

      anything that needs your voice or decision.

    2. 2

      Draft ready:

      replies they've written for you to approve and send.

    3. 3

      Handled:

      scheduling, confirmations, receipts, routine requests.

    4. 4

      Archive:

      newsletters, notifications, anything that needs no action.

  5. 5

    After the first month: the bigger handoffs

    Once the basics run smoothly, your assistant can take on work with more moving parts:

    The order matters less here than the principle: hand over one area at a time, agree what "done" looks like, and check in weekly before you move on to the next.

    • Travel: flights, hotels and itineraries within rules you set (budget, airlines, seat preferences).
    • Expenses and invoices: collecting receipts, chasing unpaid invoices and preparing expense reports, with someone else approving payments.
    • Recurring reports: pulling together weekly numbers or updates from your tools.
    • Projects: event planning, vendor research, organizing a hiring process or an offsite.
    • Gatekeeping: handling requests for your time so only the right ones reach you.

What to keep for yourself

Delegation isn't about handing over everything. Keep these, at least at first:

  • Decisions only you can make, such as hiring, pricing, strategy and anything with legal weight.
  • Relationships that depend on you personally, like key customers, investors and your co-founder.
  • Approving payments. Your assistant can prepare them. Someone else should click "pay".
  • Your own thinking time. Ask your assistant to protect it, not fill it.

Share access the safe way

This is where many first handoffs go wrong. Don't send your passwords by email or chat. There are better tools, and they're free or close to it.

Use delegation features instead of your login

Gmail lets you add a delegate who can read, send and delete email on your behalf without knowing your password. Their own address appears when they send. You can remove a delegate at any time from Gmail's settings. Calendar sharing works the same way.

Use a password manager for everything else

For tools that don't support delegation, share individual logins through a password manager's sharing feature rather than copying passwords around. The US Cybersecurity and Infrastructure Security Agency (CISA) suggests passwords that are at least 16 characters, random and unique to each account, stored in a password manager.

Turn on multifactor authentication (MFA)

CISA's guidance is to require MFA, starting with admin and high-value accounts, and to use phishing-resistant options where possible. Agree up front how your assistant will handle codes for shared accounts, so you're not texting codes back and forth across time zones.

Grant the least access the work needs

Add access as each new area is handed over, not all on day one. Keep a simple list of what they can reach, so it's easy to review. Our cybersecurity roles page has more on building access controls as you grow.

Make time zones work for you

If your assistant is in South Africa and you're in the US, the time difference can become an advantage. Your inbox can be triaged, your day prepared and your follow-ups drafted before you're up. The key is agreeing a daily overlap window for anything urgent. Our guide to South Africa and US time zones covers how to plan it, including the twice-yearly daylight-saving shift.

A weekly rhythm that keeps it working

A 30-minute weekly check-in keeps everything on track:

what went well and what needed fixing

any rules to add or change

what to hand over next

the week ahead: priorities, travel and anything unusual

Keep a running "how I like things done" doc that your assistant updates after each check-in. Within a couple of months, it becomes the playbook for the role.

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See how we find executive assistants and the wider range of virtual assistant roles. Or book a call to talk through what you'd hand over first.

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