I want to describe a feeling and see if you recognise it. You open your inbox on a Monday. There are sixty-three unread. Four of them matter a great deal, nine need a two-line reply, and the rest are noise. You know this. And yet the act of finding the four, deciding about the nine, and ignoring the fifty costs you something that has nothing to do with time. It costs you nerve. Every message is a small decision, some of them carry a little dread, and by the time you have worked through them you have spent the best hour of your day on sorting.

I run several businesses and that was my Monday for years. It isn’t any more, and the reason is not discipline. I built myself an executive assistant.

What it actually does

Nothing exotic. Before I am up, it reads the inbox, the calendar and the task board across each of my businesses. It works out what is waiting on me as opposed to what merely arrived. Then it hands me one brief in four parts: your turn, due, in flight, watch. The things only I can move. The things with a date on them. The things other people are moving. The things that might go wrong.

For the mail that needs a reply, it drafts one. Not a template. A reply that has read the thread, knows who the person is, knows what we agreed last time, and says the thing I would have said, in about a third of the words I would have used.

Then it stops. It never sends anything. Every outward action is a draft waiting for me, and that rule is enforced in the code rather than in my good intentions. I read, I change a word, I press send. The relationship is still mine. The thirty minutes of composing is not.

How much of the job is this?

Here is the claim I would make about most knowledge roles, and about an executive assistant in particular: somewhere between half and four-fifths of the work is repetitive. Reading, sorting, chasing, filing, reminding, summarising, drafting the predictable reply. That part a well-built AI does very well, every day, without getting bored and without forgetting the thing you said in March.

The remaining part is judgement and relationship: knowing that this client needs a phone call rather than an email, that this meeting should be declined kindly, that this week is not the week to raise it. That part stays human. For most founders and small teams there was never a human assistant to do it, so in practice the judgement stays with you, and you get to spend your nerve there instead of on sorting.

The question I keep asking myself

Is a hand-written email still the point?

I have come to an answer I did not expect. For years I believed the personal touch was the value: I wrote it, in my voice, with care. What I actually produced, a lot of the time, was a long email written late, slightly defensive if the topic was awkward, with the one thing the reader needed buried in the third paragraph. It took half an hour and it was not my best work.

What people want from me, clients, team, leads, is clarity. What is happening, what I need from them, by when. Professional, succinct, unemotive in the good sense: no heat, no hedging, no throat-clearing. An assistant that drafts that, in thirty seconds, from the actual thread, lifts the standard of my communication across the board. I will happily accept a slightly less personal feel for that. And the honest truth is that the emails where the personal touch really matters, a condolence, a hard conversation, a thank you that needs to land, are perhaps one in fifty. Those I still write by hand. Now I have the energy to.

If you want to build one

You do not need my setup. The small version takes an afternoon.

  1. Connect Claude to your mail, calendar and files on a paid plan, with training on your data switched off.
  2. Ask it one question every morning: what is waiting on me, ranked, and what can wait? Correct it when it gets the ranking wrong. It learns your priorities faster than a new hire.
  3. Have it draft, never send. Make that a rule you do not break, however good it gets.
  4. Give it your voice. Paste in ten emails you are proud of and tell it what you like about them. Short. Plain. No exclamation marks. Whatever yours is.
  5. Let it run on a schedule once you trust the morning question, so the brief is there before you are.

The bigger version, the one that spans several businesses and talks to the accounting system and the task board, is a build. It is also the most valuable thing I own, and it is the kind of thing I build for other people now.

The honest caveat

It will occasionally be confidently wrong about who someone is or what was agreed. That is why it drafts and you send. Treat it like a very good new assistant in their second month: fast, tireless, right most of the time, and not yet someone you would let sign for you.

If your inbox costs you more nerve than time, send me a description of your week and the tools you live in. I will tell you honestly how much of it an assistant could carry, and whether you need me to build it or an afternoon to set it up yourself.