Playbook · Less checking up · 6-min read

Stop bossing your agent around

If you have to keep checking on an agent, it isn’t saving you much time. Set a few rules up front and let the built-in approvals do their job. Then do one short check-in each week.

1. Write the rules once

Paste this into your custom instructions or project instructions, or into the rules for an always-on agent. These are my rules, not a vendor’s. Change them to fit your family.

Ground rules for helping my family (read these before every task):
1. Ask me before you buy, book, send, post, cancel or delete anything. No exceptions.
2. If a task needs a login, a payment or a form with our personal details, stop and hand it back to me.
3. If you're not sure, do the smaller, safer version and tell me what you skipped.
4. Keep results short: what you did, what's waiting on me, and anything that went wrong.
5. Don't contact anyone on my behalf. Draft it, and I'll send it.
6. If something keeps failing, stop after two tries and tell me. Don't keep retrying.

2. Know what each assistant already asks you about

AssistantBuilt-in brakes
ChatGPT tasksActions that send a message or change outside data may need your approval, and the task pauses until you review it.[1]
ChatGPT Dot (Pro only)The always-on agent supports custom rules, like “ask before…”. It’s only on Pro (from $100/mo) and Business Premium.[2]
Claude scheduled tasksWhen you set up a task by hand, you choose an approval mode.[3]
Copilot TasksAsks for approval or hands control back before payments, sending personal info, emailing or messaging people, account changes and sensitive actions. For recurring tasks, it may ask for approvals during setup so the task can run unattended.[4]

My advice: don’t pre-approve “send” or “buy” on anything that runs on a schedule. Reviewing a draft takes a few seconds, and fixing a wrong email to the school takes a lot longer.

3. The 10-minute weekly check-in

Weekly check-in (Sunday, 10 minutes):
[ ] Open the Scheduled / Tasks page. Did every task run this week? Any paused?
[ ] Any approvals waiting on me? Approve or say no.
[ ] Read last week's results. Was each one actually used? If not twice in a row, pause it.
[ ] Fix one thing: tighten one prompt that gave a bad answer.
[ ] Check connected apps (Gmail, Calendar, Drive). Still the right account? Anything to disconnect?
[ ] Skim the last few digests and briefs. Anything we skip every week? Cut it.

This matters because tasks can stop without telling you. ChatGPT pauses inactive tasks and ones waiting on you,[1] and Gemini can switch off a schedule you’ve stopped opening.[5] Microsoft also warns that Copilot can make mistakes or be tricked by hidden instructions on websites, and says to watch results closely for anything involving payments, personal info or messages.[4]

4. When to use an agent at all

  • Use a scheduled prompt for anything that ends in a list or a plan: the school email digest, the week ahead, the grocery list, chores. No agent needed.
  • Use an agent only for multi-step chores on websites you trust, like comparing three quotes or finding open appointment slots. Watch the first few runs, and keep booking and paying for yourself.
  • Skip it if you’d spend more time checking its work than doing the job yourself.

These are my rules of thumb, not cited facts.

Tested by Dave Not yet

I haven’t run this exact setup with my family for a full week yet. When I do, this box will say what happened, good or bad.