Build a personal executive assistant that turns calendar and inbox signals into a focused daily brief, while keeping permissions narrow and every consequential action visible to you.
Source episode · 05:00
How I AI: Webflow CPO Rachel Wolan's AI Chief of Staff & Org Adoption Playbookwith Claire Vo
Rachel connects a personal chief-of-staff app to read-only calendar access and limited Gmail actions, then uses it to critique her schedule, suggest delegation, and triage her inbox.
A daily brief that identifies priorities, schedule conflicts, delegation candidates, and emails needing attention, with drafts rather than autonomous sends.
Anthropic AI assistant
Claude for coding tasks
Step by step
Follow the sequence once, then adapt the prompts, checks, and handoffs to your own setup.
4 steps
Connect the private app to Google Calendar and Gmail through official APIs. Store secrets outside the repository, grant calendar read-only access, and limit Gmail to reading, labeling, archiving, and creating drafts.
Run a daily calendar prompt that compares the next day with your stated priorities, flags conflicts and missing preparation, and suggests meetings to shorten, move async, or delegate.
Analyze tomorrow’s calendar against these priorities: [priorities]. Return: top three outcomes, preparation needed, schedule conflicts, meetings that could be async, delegation candidates with a reason and suggested owner, and protected focus time. Cite the event title and time for every recommendation. Do not change the calendar.
Add a direct feedback section that compares recent time allocation with the executive work you intend to do. Require evidence from the calendar and separate observed patterns from interpretation.
Using the last [period] of calendar data, compare my time with these responsibilities: [responsibilities]. State the most important mismatch, cite the events behind it, name one high-leverage change, and identify any data limitation. Be direct, but do not exaggerate certainty.
Add inbox triage in report-only mode first. Classify messages that need a decision, document, relationship response, or no action; draft replies only for defined cases and never send them automatically.
Triage messages from [window]. Keep: decisions, requested documents, active partner or customer threads, and messages from [important people]. Suggest labels and archive candidates with reasons. Draft replies only for [approved cases]. List every proposed archive and draft so I can inspect them before any action.
Turn an idea into a PRD, user stories, and a plan.
After the steps
How to recover when the loop fails and where human judgment helps.
Recover
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