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jack in the loop
chapter 07 of 11

chapter 07

When Claude hands back to you

Money, contracts, anything sent in your name, family, and final picks. What Claude does in each case, what you do, and the words that make it stop and ask.

A good assistant knows where its job stops. The project instructions in chapter 2 tell Claude to put "FOR YOU:" at the top of anything in these areas and stop. Here's what that looks like in practice, area by area.

AreaClaude doesYou do
MoneyAdds up quotes, tracks what's due, warns when you're overPay, agree amounts, decide what to cut
ContractsFinds clauses, explains them, drafts questionsNegotiate, decide, sign, get a lawyer when it matters
Sent in your nameDrafts emails and messagesRead, edit, send
Family and guestsHelps you find the words, lays out optionsHave the conversation, make the call
Final picksNarrows the field, lays out trade-offsChoose

Money

Claude should never touch a payment, and it shouldn't hold the details to make one. Keep card numbers, bank details and logins out of chats, out of project files and out of the sheet.

What Claude is good at here is warning you early. Ask it, in the weekly check-in, what's due in the next 30 days and where the budget is heading.

Read the Budget and Quotes tabs. What payments are due in the next 30 days, and to whom? Compared with the total budget in Details, are we on track, and if not, which three categories are furthest over their estimate? Don't suggest cuts to anything in our top three priorities.

Anything sent in your name

Covered in chapter 6, and worth repeating: Claude drafts, you send. That includes emails, texts, comments on a vendor's portal, RSVPs on someone else's site and messages to family. If someone thinks they're hearing from you, it should be you.

The same goes for any tool that can act for you. Gmail's connector can send once you approve it. Cowork, on paid plans, can work with files on your computer. Anthropic's safety page for Cowork advises not giving it access to files with sensitive information, such as financial documents, and to keep backups. For wedding planning, there's no need to give any tool the power to send or pay for you, so don't.

Family and guests

This is where you want Claude's help with words and not with judgement. It doesn't know your family, and the most important facts are usually the ones nobody writes down.

Good uses:

I need to tell my aunt we're not inviting children. She has two. Help me write a kind, clear message that doesn't over-explain. Give me two versions: one for a text, one for a phone call I can glance at.
Here are four ways we could seat the head table. For each, list who's next to whom and what could go wrong. Don't pick one.

Two privacy notes. Keep the private detail out: "keep these two apart" is enough. And remember that a shared chat link shows the whole conversation up to the moment you shared it, so don't share a chat that has family business in it.

Final picks

Claude can get you from forty venues to three. It shouldn't pick the one. It hasn't stood in the room, and it can't tell whether the coordinator made you feel looked after or rushed.

Ask for the decision laid out, not made:

FOR US: we need to pick between Hollow Pine Barn and Stone Mill Hall (both made up for this example). From the sheet, give us a side-by-side: total cost, deposit and refund terms, date-change terms, capacity, access, what's included, and what we'd still have to rent. Then list the questions that would change the answer. Don't recommend one.

Then decide together, and log it in the Decisions tab: what you chose, what else you looked at, and why.

When Claude is just wrong

It will be, sometimes: a venue that closed, a capacity from an old page, a total that missed a line. Anthropic's help page asks you to check Claude's sources and scrutinize high-stakes advice. A good habit: nothing becomes a fact in the sheet until one of you has seen it at the source.

sources · checked October 25, 2026