People waiting on the founder: a reply, a decision, an intro.
Checklist · For founders
The first 30 days with your first EA
The Handover: 3 lists, 4 stages. So nothing you already owe slips while your new EA learns your inbox.
Download the PDF · Markdown for your AI assistant · Use it with ChatGPT or Claude
I've sat on both sides of this desk: as a remote assistant to a US executive, and as a founder. The executive once told me she sometimes forgot what she'd asked me to do, and that my updates were how she remembered. That is the whole job: make the work visible before anyone has to ask.
An EA or another AI agent?
An agent does what you remember to ask. An EA catches what you forgot. If your bottleneck is tasks, get an agent. If it's people waiting on you, get a human.
Signs it's time for a human:
- More people are waiting on you than tasks are.
- You find out something slipped by accident, because you happened to ask.
- Your team says "waiting on you" every week. You are the approval queue.
- You write "I'll send it" more often than you send it.
- Your best investors and customers get your leftovers.
- You reread your own inbox to remember what you promised.
A good EA isn't hours you buy. It's the part of your head that keeps track of everyone, handed to someone you trust. That's the time you get back.
The 3 lists
Everything the founder said they would do: "next week", "I'll send it", "let me check".
Threads that mattered and went silent: a warm investor, a customer who stopped replying.
Every stage below moves these three lists from the founder's head to the EA's hands.
The 4 stages
Build the 3 lists together from the last 30 days of email. Then ask: "who would you be embarrassed to make wait?" The names they hesitate on go to the top.
The EA drafts, the founder sends. Agree which emails the EA answers alone, which need a draft first, and which never. The EA sends the update before the founder asks.
The EA owns Waiting and Promised, and writes in the founder's name by the rules you agreed, from the inbox you agreed. The founder gets one message a day: decisions only.
A 20-minute review of the 3 lists every week. Two tests: nobody waits more than 2 days, and no promise is found by accident.
The daily 10 minutes
- Start with yesterday's sent folder: look for "I'll", "next week" and "let me check". Then the calendar. New mail last.
- Never close a thread with "noted". If it can't be closed, write down who's waiting and by when.
Use it with your AI assistant
Paste the markdown version into ChatGPT, Claude or your own agent, then this prompt. If your agent can read your email, it drafts the 3 lists for you.
You are helping a founder hand their inbox over to a new executive assistant using The Handover (sidekicklog.com/handover.md). 1. Ask me 5 short questions about my work, my most important relationships and how I like to be interrupted. 2. Draft my 3 lists (Waiting, Promised, Quiet) from what I share with you. For each item: who, what they're waiting for or what I promised, since when. 3. Put the names I'd be most embarrassed to make wait at the top. 4. Then write a one-page plan for the 4 stages, with my EA's name, the start date and what my EA can answer alone, draft first, or never touch. Keep it short. Ask before assuming.
Skip Day 1
Sidekick Log reads the founder's Gmail and builds the lists for you: who's waiting, what was promised, what went quiet. Read-only, it never sends.