Automate Your Week with Cowork Routines

The one sentence behind each question, say these as you go: (1) If it needs your judgment, taste or relationships, it is a task you run and review, not a schedule. (2) Nothing that touches sensitive files, sends messages for you, makes purchases, or is hard to undo. (3) If the real trigger is an event, you will run it when nothing changed or miss the thing that did. (4) A schedule does not fix a process, it repeats it on time, forever, broken parts included.

This is the slide the signup page actually sold, so give it the time. Take two or three answers from chat and run them through the four questions out loud. Half will fail and saying exactly why is the lesson. The one that passes cleanly becomes your live build, say so on air. Question 3 is the one people argue with, so have the example ready: "tell me when a contract is signed" is an event, not a schedule, and a daily timer gives you 364 useless runs and one late one. Question 2 is Anthropic's own written guidance, quote it as such.

The diagram replaces cards 1 and 2. The full line behind each: (1) No "as we discussed", no "the usual format". Write it for someone who has read nothing. (2) To compare against last week it must write last week's result down and read it back. (3) Exact format, exact sources, exact scope. A first day hire cannot infer your standard.

This frame explains every rule in the rest of the session, so land it properly. The contrast worth saying out loud: a reminder tells you to do the work and only needs a time and a label, a scheduled task does the work and needs everything you would give a person on their first day. The state on disk point is what people thank you for later, it is the difference between a tracker that says "here are their prices" every week and one that says "they changed this since Monday". If asked whether it remembers across runs: no, and that is a feature, because a fresh session cannot drift.

Presenter reminder: narrate the decisions, not the clicks, then press Run Now before you leave the screen. This slide stays up for the whole build, timer top right. Use the task you picked from chat. Narrate the decisions, not the clicks, the clicks are obvious and the decisions are the content. Do Run Now at the end so they see a real result before you leave the screen, that is what makes the promise true. Read this strong prompt out loud as your model of a good one: "Every Monday open these three URLs, read the pricing page on each, compare against competitor_notes_last_week.md in this folder, write a new dated file listing only what changed with the URL and date beside each claim, and if a page did not load or nothing changed say that at the top instead of writing a normal report, then overwrite competitor_notes_last_week.md with this week's findings." It works because it tells a stranger where to look, what to compare, what to write, and what to do when things go wrong. Contrast with "check our competitors every Monday and tell me what changed".

The full line behind each card: (1) Read the execution log, not just the output, then watch the first three to five runs. (2) Put this in the prompt: if a step failed, a source was unreachable, or nothing changed, say so at the top.

Be honest here, it buys the room. The Cowork changelog from the last two months is full of real scheduling bugs: cron using 7 for Sunday never firing, every N days schedules landing on the wrong days, re enabling a task kicking off catch up runs for every missed slot, runs dying behind a VPN after the machine woke. Anthropic has since added automatic retries at 5, 15 and 30 minutes when a run cannot reach the model. Naming one of these is worth more than polish because everyone here has been burned by a cron job. Also worth saying: Automatically Approve uses more of your allowance because of that safety checking, and Skip All Approvals meaningfully raises prompt injection exposure, which is why it is never right for anything reading the open web.

Tell them to screenshot the table. One spoken mention of the course, then straight to questions, no selling. Maven adds every signup to the waitlist and emails the recording in 48 hours, the work is done. Held for Q&A: how Cowork scheduled tasks differ from desktop local routines, slash loop and cloud routines, running against a git repo, chaining tasks, usage cost.