The weekly check-in

Everything in this guide only works if the sheet stays current and somebody looks at it. A long project doesn't fail in one big moment. It drifts: a follow-up that nobody sent, a deposit date nobody saw, a decision made in one chat that the other person never heard about.

The fix is small and boring. Once a week, the two of you sit down together for half an hour with the sheet and one chat.

Before you sit down (five minutes each)

• Log any emails or calls from the week in Outreach. If you haven't, ask Claude to find them (chapter 6).
• Update the stage and next action on every vendor you own.
• Tick off tasks you finished.

The check-in prompt

Start a new chat in one of your projects each week. A fresh chat reads the sheet as it is today, without last week's conversation getting in the way.

Weekly check-in. Read our "Wedding planning" sheet and give us:

1. What moved this week (vendors that changed stage, tasks done, replies in).
2. Overdue: next actions and follow-ups past their date, with owner.
3. Waiting on: who we're waiting for, and since when.
4. Money: payments due in the next 30 days, and contracted vs. total budget.
5. Guests: RSVPs in and still pending, against the target.
6. Decisions we need to make this week, marked FOR US, with the options.
7. Your suggestion for our top three for next week, with an owner each.

Keep it short. Tables where it helps. Then give me the row for the Check-ins tab (week of, what moved, decisions needed, waiting on, money due, top three).

Then talk. Make the decisions you can, log them in Decisions, add the check-in row, and agree the top three. That's it.

Sam and Riley's check-in (made up)

Two venue quotes in. Stone Mill hasn't answered about date changes after five working days, so Riley's sending the follow-up. Nothing due for 30 days. Decision for this week: Hollow Pine or Stone Mill, once Stone Mill answers. Top three: pick the venue, first pass at the guest list, email two bands.

Keeping the project healthy

Once a month, add five minutes for upkeep:

• Re-read the project instructions. If you keep correcting Claude on the same thing, the fix belongs in the instructions doc, then in both projects.
• Refresh the brief in project knowledge if anything changed.
• Check memory. Each project has its own memory, and you can see and edit what it holds in Settings. Delete anything out of date, so it doesn't creep back into answers.
• Filter the Vendors tab to hide Booked and Passed, so you see only what's still live.

Can it run itself?

Partly, if you're on a paid plan. Cowork, on Pro, Max, Team and Enterprise, can save a task and run it on a schedule you choose, and scheduled tasks run in the cloud, so your computer doesn't need to be on. A Sunday-morning summary of the sheet, waiting for you when you sit down, is a reasonable use.

Keep a scheduled task to reading and summarizing. Don't give it a job that sends, books or pays. Anthropic's own safety guidance for Cowork warns that content Claude reads mid-task can carry hidden instructions it might act on before you notice. Your inbox is full of content from strangers. The check-in itself, the half hour where you two decide, is the part that shouldn't be automated anyway.

On the day

In the last couple of weeks the sheet becomes a run sheet. Ask Claude to turn the Vendors tab into a one-page list for whoever's coordinating on the day: every vendor, arrival time, contact name and phone, what they're bringing, and what's already paid. Print two copies. Give one to someone who isn't either of you.

Then put your phones away. The project's done.