Quick answer
Assistant work repeats four jobs daily: inbox and calendar triage, meeting capture, briefing documents, and the research behind a trip or a vendor. AI helps with all four the same way — a first pass you correct. It should not hold the judgement that makes the role valuable: what the principal needs to see, who gets prioritised when the day collapses, and what never leaves a personal inbox.
What an assistant should not hand over
- Approvals and commitments. A draft saying "confirmed for Tuesday" commits someone else's time. Accept after the calendar and the principal both say yes.
- Personnel and candidate material. Performance notes, interview feedback, salary, and health details do not belong in a consumer tool, whatever the prompt — it is not covered by your employer's agreements with the employee.
- Access decisions. Delegated calendar and mailbox access, and any assistant that can send mail or book rooms, needs the approval a person would get. Check whether it reads or acts before you authorise.
The shortlist, by job
ChatGPT
4.8/5 editorialThe general first pass: a thread turned into a three-line update, an agenda from a topic list, a difficult email rehearsed in two tones. Its weakness is the one that matters here — it will state a fact about a person, a date, or a policy with no basis. Feed it the real material and keep the verification line.
Claude
4.7/5 editorialLong documents and instruction-heavy work: a board pack, a supplier contract, a policy summarised without losing its exceptions. It holds a long brief more steadily; the other rewrites more gracefully. Test both on your own material before paying.
Shortwave
4.5/5 editorialInbox triage on top of the mail account rather than beside it — summaries, grouping, and draft replies in a Gmail-shaped client. It fits a work account you control; delegated access to a principal's mailbox is an IT permissions question, not a vendor feature.
Fathom
4.3/5 editorialCapture with the summary, decisions, and action items separated — the structure that turns a call into follow-ups without re-listening. Its free tier covers recording and summaries at useful volume. A shared recording of a sensitive conversation is a data-handling decision, not a convenience.
Notion AI
4.3/5 editorialWhere briefing material lives: principal preferences, recurring logistics, supplier contacts, travel notes, and the "how we do this" pages that make a role transferable. AI drafts from those pages, so answers are grounded in your notes. It only works if the pages exist and are current; the free tier's AI is a trial.
Perplexity
4.6/5 editorialCited lookups — a venue's capacity, a visa rule, a supplier's ownership. The citations are the point: you can hand over a link rather than an assertion. Open the source first, since a citation proves the page exists, not that the number is current.
Where the four jobs rank
- Inbox triage — highest return, lowest risk. Summarise, group, draft. Nothing sends itself, and the time saved is daily.
- Meeting capture — high return, easy to get wrong on data. The summary is useful; recording a confidential call is a deliberate decision.
- Briefing and deck drafting — moderate return, high visibility. One page per trip or meeting is a strong use. Gamma or Canva can lay out your outline; the content stays yours.
- Judgement calls — keep off the list. Prioritising the principal's day and choosing what to escalate are the role, not the overhead.
Permissions before subscriptions
Most risk in this role arrives through access, not prompts. Three questions decide whether a tool is usable: can it read the principal's mail and calendar or only yours; can it send, book, or invite on its own, and is that logged where you can audit it; and is the tier you are on covered by the organisation's data terms, or is it a personal plan with consumer retention. Supporting more than one principal, assume it can see everything unless you set it otherwise. What to ask before connecting an AI tool to company data is the checklist for that conversation with IT.
Before you pay for anything
Start with what your organisation already licenses — many assistants are bundled into a workspace plan, and a second personal subscription buys the same model with worse terms. Then test against one real week: how many drafts you accepted unchanged, how many you rewrote, which limit interrupted you first. Record it on the free scorecard and fold the result into a monthly cost review. Do you need paid AI plans? is the test for where free stops working.
Frequently asked questions
Can an executive assistant use AI on a principal's calendar?
Only with access granted the way you would grant it to a colleague, and only if the tool is covered by your organisation's terms. Reading a calendar is one permission; accepting invites or booking rooms for someone else is another.
Which AI tool is best for meeting notes?
A recorder that separates decisions and action items from the transcript is the useful shape. Free tiers are usually enough to test one meeting type twice and compare the notes.
Is it safe to put confidential documents into an AI assistant?
Not by default. Board papers, contracts, and personnel material need a tier whose retention terms your organisation has accepted. A personal subscription is not a data-processing agreement.
Related reading
Meeting notes to CRM, automatically covers capture end to end, how to pick one notes tool is the keep-one test, and best AI tools for project managers is the adjacent guide.