Run a personal chief of staff with daily briefings and reviews
A consultant set up Claude Cowork as a chief of staff that reads three calendars, a task board and notes, sends a morning briefing and a Sunday review, and keeps a personal contact file up to date.
What they did
He pointed Cowork at a synced folder organised by projects and areas, with a CLAUDE.md of preferences and people, a markdown task board capped at three items in progress, and a process file. Connectors cover Google Calendar across two accounts, Trello, Apple Notes, Perplexity and an email address the assistant uses. Scheduled tasks run a briefing at 8:00 each day and a weekly review on Sundays, and he dictates notes from his phone that get filed under the right project.
What happened
The poster says it caught a rental car cancellation deadline, a breach of his work in progress limit, and a promise he had made to tell bandmates about a vacation.
Keep in mind
Cowork forgets anything not written to files, Google Calendar auth and Chrome debugging took workarounds, and forwarded email is only processed while a session is open. It reacts rather than acting on its own.
Try it with your agent
Act as my chief of staff using the files in <your work folder>. Every morning at <time>, brief me on today's events from <your calendars>, open tasks, follow ups I owe people, and any deadlines in the next two weeks. Every <day>, run a weekly review that looks three weeks ahead. Write everything you learn about my projects and contacts into files so nothing is lost between sessions.
Replace the <angle brackets> with your own details.