Have you connected an AI assistant to your email and calendar to list what you owe and what you are waiting on?

Copilot, Gemini, Claude or ChatGPT, when connected to your work accounts, can scan recent messages and give you a daily list of open loops and meeting prep. It reads; it does not send anything.

How to automate it

How to automate “keep track of what I delegated and whether it got done”

Here are 2 ways to spend less time on this, best first. Each comes with steps you can follow today and, for AI fixes, a prompt to copy.

20 min

typically, every day

50%

of the time can be automated

Easy

to set up

Fix 1 of 2

AIBest fix

Run a daily AI chief-of-staff brief across email, calendar and notes

Assistants connected to your email, calendar and documents can list what you promised, what you are waiting on and what today's meetings need, so fewer things slip.

Typically saves about 40% of the time20 min to set up

1Use an assistant that can connect to your work email and calendar with IT approval: Microsoft Copilot, Gemini in Google Workspace, Claude (connectors) or ChatGPT (plugins) for Gmail and Google Calendar or Outlook.
2Each morning, run the prompt below (save it as a reusable prompt or scheduled task if your tool supports it).
3Move the open loops into your task list or tracker.
4At the end of the week, ask for everything you delegated that has had no reply.

Prompt to copy

Act as my chief of staff. Look at my email and chat from the last [3] days, my calendar for today and tomorrow, and my meeting notes. Give me: 1) things I promised to do, with who and when, 2) things I delegated or asked for that have had no reply, 3) for each meeting today, one line on the purpose and what I need to bring or decide, 4) anything that looks urgent that I have not answered. Link to the source for each item. Do not send anything.

Tools: Microsoft Copilot · Gemini in Google Workspace · Claude with Gmail and Calendar connectors · ChatGPT with Gmail and Calendar plugins

Fix 2 of 2

Process fix

Keep one list of delegated actions, each with an owner and date

Follow-up time drops when every delegated item lives in one place that the owner updates, and you review it at a set time instead of asking around.

Typically saves about 30% of the time30 min to set up

1Create one list or board: action, owner, due date, status.
2Every time you delegate something in a meeting or message, add it before you move on (or let your AI notetaker add action items).
3Ask owners to update status themselves.
4Review the list once a week, or in each 1:1, and close or re-date items.

Tools: Asana, Linear, Jira, Monday, Todoist or Microsoft Planner

Quick wins

Have you tried…

Have you connected an AI assistant to your email and calendar to list what you owe and what you are waiting on?: Copilot, Gemini, Claude or ChatGPT, when connected to your work accounts, can scan recent messages and give you a daily list of open loops and meeting prep. It reads; it does not send anything.

Who does this task

Roles in our library that list this as one of their common tasks. Each guide covers the rest of that role’s week.

CEO / Founder General Manager / VP Chief of Staff

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