AI for Executive Assistants in 2026: Delegated Inboxes, Holds and Travel

AI can summarize threads, draft replies, build itineraries and sort receipts for an executive assistant today. It can't decide who gets your executive's time, and some of the best-known tools stop working or stop acting inside a delegated mailbox. So the first question isn't which tool is smartest. It's whose account it runs on.

Much of what you'll find on this topic reviews software meant to stand in for an assistant, written for the executive buying it. This page is for the person holding delegate access, and it's honest about the awkward part: most AI products assume one person, one inbox. Tools below are examples checked on each vendor's own pages, not a ranking.

Does the AI work in a mailbox that isn't yours?

Often only partly. Google lists Gemini in Gmail among the features delegates can't use, and Microsoft says Copilot in a delegated mailbox can summarize and draft but can't yet send or schedule. Check this before you pay for or learn anything.

Your own access has edges too. A Gmail delegate can read, send and delete, and Google says your outgoing messages show both your address and your executive's, so the signature shouldn't pretend otherwise. Calendar is a separate grant. If you have calendar access but not mail, Google warns that answering an invite from the email notification puts the event on your calendar, not theirs. Answer from their calendar instead.

For a third-party assistant, ask the vendor three things before connecting anything: does it work through delegate access or does it need the executive's own sign-in, does it send anything without a person confirming, and who else can see the history? Fyxer and similar inbox assistants pitch themselves on connecting an inbox and drafting in the owner's voice, which is a different setup from two people working one mailbox. On Google Workspace, your admin also can block third-party apps or restrict their Gmail and Calendar access, so a tool may simply refuse to connect.

Where an executive assistant's week goes

Calendars and email take the largest share. In a 2025 survey of 600 executive assistants, 29.3% said scheduling and calendar management took most of their time, 21.5% said email, 13.5% travel booking and 7.2% event and meeting prep. Respondents came from a calendar vendor's EA community and the answers are self-reported, so read it as a rough sketch of the job.

O*NET's task list fills in what the survey groups together: sorting incoming correspondence, deciding whether visitors get access, arranging catering for board and committee meetings, recording and distributing minutes. The same survey found 70% of respondents use ChatGPT and 43% use Microsoft Copilot. It doesn't say on whose account, and that's the question your IT team will care about.

Five jobs, and how far AI gets in each

Holds and rebooking

Calendar software is further along here than chat assistants, because it can touch the calendar. Vimcal EA sits on top of Google Calendar or Outlook, creates holds when you offer times and removes them when someone confirms, and shows up to five time zones. It costs $85 a month, or $68.75 a month billed yearly. Its features page doesn't name AI features, so this is plain automation, which is what most stale-hold problems need. Vimcal also ran the survey above.

Reclaim's guide for assistants, written for its older version, has you and your executive on separate accounts in one team. They grant access, and you switch into their account under a warning banner. You can do nearly everything they can, except delete the account, change its calendars or manage API keys. Check the current steps with Reclaim before relying on this. See how Reclaim compares if it isn't a fit.

No tool knows that the Thursday 1:1 only looks movable. Keep that judgment, and let a chat assistant do the arithmetic once you've stripped out the titles:

My executive's flight now lands at [new time], not [old time].
Affected meetings, titles removed:
A: external, [duration], [other party's time zone]
B: internal, [duration], can be remote
C: internal, [duration], must be in person
Open slots in the next five working days: [list]
Rules: nothing before [time]. Leave [minutes] between the airport and the first meeting.
Give me two ways to rearrange these and say what each one costs.
Don't invent a slot that isn't on my list.

One more limit is worth raising with your executive. On a shared Google Calendar, a private event marked Busy shows as a block with no details, and one marked Free doesn't appear at all. A scheduling tool can only protect time it can see, so agree how the medical appointment should be marked.

Travel

Itineraries are the safest place to start, because the input is already a booking confirmation. TripIt builds a trip from booking confirmations forwarded to plans@tripit.com for free, and its Pro plan adds real-time flight alerts, fare refund monitoring and check-in reminders for $49 a year. If your company books through Navan, its delegate page says traveler preferences and passport and loyalty details are already there when you book for someone else, and Navan says its AI travel agent handles rebookings and hotel changes, with human agents for harder cases.

What stays yours is knowing that your executive would rather land at midnight than risk a tight connection before a board day. Keep passport numbers and home addresses out of general chat tools, since a travel platform is built to hold them and a chat history isn't.

Expenses

AI reads the receipt; you supply the reason. Expensify's Concierge creates expenses from receipt images, auto-categorizes them and can flag receipts that may be AI-generated. For delegated work, Expensify's Copilot access (a role name, unrelated to Microsoft's product) labels your actions as done on the owner's behalf. Ask for Limited rather than Full: Limited lets you manage expenses and reports but blocks approvals, payments, rejections and holds.

The IRS shows why the human part remains. Publication 463 calls for receipts for all lodging and for other expenses of $75 or more, plus a record of the business purpose. A dinner receipt gives the amount and the restaurant. Only you know what the dinner was for, and your finance policy may ask for more than the IRS does.

Gatekeeping

Gatekeeping is the job AI should touch least, and it gets harder as AI spreads. The FBI has warned of AI-generated voice messages impersonating senior U.S. officials, and says clones can sound nearly identical to the real person. The campaign it describes targeted government officials, but a request in your executive's voice to move money or share a code should get the same treatment: call back on a number you've confirmed independently, and verify any request for money or gift cards.

Reading mail with an AI also adds a new way in. Google describes indirect prompt injection as instructions hidden in content the AI later reads, such as an email, and uses confirmation steps for risky actions as one defense. So an assistant with send rights on an executive's mailbox should stop and ask you before it acts. Summaries are lower risk than actions, and a first draft of "they can't make that work this quarter" is a fine use. Deciding that the sender is someone your executive will always make time for isn't.

Meeting logistics

Agendas and run-of-show drafts are good chat work, as long as the catering headcount and the room booking get confirmed by a person. Minutes need more care. The law firm Cooley advises that AI note-taking tools should not be used in board or committee meetings, citing confidentiality, privilege, candor and discoverability, and because human note takers choose what goes in. If you take those minutes, this protects you too: the judgment about what belongs in the record is the skill.

For ordinary meetings, say when a call is being recorded. California, for one, requires consent from everyone in a confidential conversation, and one call can include people in several states.

Merlin for an EA: your own desk, not the executive's mailbox

Merlin suits your own relationships better than your executive's mailbox. Our Mac assistant reads whichever Google account you connect by signing in to it, which isn't the same as acting as a delegate on one. Don't assume a delegated mailbox appears under your own login.

• Your own desk: the People panel names the fellow assistant or caterer whose message to your own address has gone without a reply for anywhere from two days to a month. Calls don't clear them, since the panel only looks at mail.
• Attendee availability: ask whether someone is free Thursday at 3 and Merlin checks free and busy times for up to ten people, for calendars shared with your connected account. When it can't see a calendar, it says so.
• Prep: for events on your connected calendar, a Meeting Brief shows up about ten minutes beforehand, and Prep me builds a sourced one on request from past notes and email threads.
• Web errands: browser tasks can handle a check-in or a booking in Merlin's own browser, and they're told to wait for you before paying for that seat or hotel. Cards and passwords aren't saved; it asks each time.
• Sending: request a reply or a moved meeting in chat and nothing happens until you've confirmed the card it shows you. Routines (scheduled tasks with nobody watching) work unattended, so don't point one at anything sent in your executive's name.

Connecting your executive's Google account is possible only by completing Google's consent screen as that account, and Merlin then reads it alongside yours. Do that only with their agreement and your IT team's, and note that an admin can block it. In an Outlook and Microsoft 365 office, Merlin has no way into your mail or calendar.

Merlin doesn't answer phones, and it isn't an expense or hold-tracking tool. It can record meetings on your Mac, with transcription on paid plans only, and there's no share button, just a way to copy the transcript. On paid plans the audio is uploaded for transcription and transcripts and notes are stored in your Merlin account, so read the privacy policy before any executive material goes near it.

Your first five moves as an EA

1. Write down your actual access: mail delegate, calendar permission level, and which private events you can't see. Most tool decisions follow from this list.
2. Ask IT one question in writing: which AI accounts are cleared for your executive's mail, calendar and travel details, and are third-party apps allowed to connect?
3. Put your executive's rules on one page: earliest meeting, buffer after flights, who always gets through. Leave out names and health details so you can paste it into a cleared tool.
4. Run one trip through an itinerary tool and compare the result with the confirmations before you trust it with the next one.
5. Agree two lines with your executive: what never goes out without you reading it, and how you'll verify an urgent request that claims to come from them.