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Field Guide · level 5 · Office work, by task

How do you plan a project or a week with AI?

Turn a goal into a tested plan with owners and dates.

5 min · try it 10 min · as of Oct 2026
Bring this to your team · Team workshopsA planning workshop on your team's real projects, from goal to tested plan. Get in touch
01

The sticky note plan

Monday, the plan fits on a sticky note. Thursday, it falls off.

02

Four moves, goal to plan

Before you share:

  1. Hand it the facts
  2. Owners and dates
  3. Test it for gaps
  4. Check the calendar
03

Hand it the facts

The goal and deadline. Who's on it. What can't move: leave, other deadlines.

04

One owner and a date

Each step gets one owner and a date. Ask which step waits for which.

My pick for handing over a task

Claude logoClaudeAlso good: ChatGPT logoChatGPT Work

Hand over a task in any chat: it plans the steps, works with your files and asks before important actions.

All my picks
05

Test it before you share

Ask it three things:

  1. What's missing?
  2. What breaks first?
  3. What goes if we lose a week?
06

Check the real calendar

Let a calendar connector read it, where your company allows. Fix clashes yourself.

07

It drafts. You own it.

Tested on Monday, it's still on the wall on Thursday.

Try it · 10 minutes

Plan one small project

Use roles, not names.

  1. Pick a small project, or next week.2 min
  2. Paste the text, fill the brackets, send.3 min
  3. Fix the table using its three answers.3 min
  4. Check each date against your calendar.2 min

The planning brief

Help me plan this. Goal: [what done looks like]. Deadline: [date]. Who's on it: [roles]. What can't move: [leave, other deadlines]. List the steps in a table: step, owner, start, due, waits for. Then tell me what's missing, what could go wrong first, and what we'd cut if we lost a week. Ask before you guess.

Good looks likeOne owner and date per step, plus a cut list.

In your assistant · as of Oct 2026 · Claude, ChatGPT, Gemini

Plan it in your assistant

Menus move often. Missing something? A rollout, your plan, country or admin may be why.

  • CheckCalendar allowed at work
  • CheckChanges need your yes
  • CheckYou check every date

My pickFor a plan that matters, Claude: Opus 5.5 at High first, then Sonnet 5.5 at High or Extra high.

Write “away” for leave, never the reason. Health and personal details stay out of the chat.

Claude

In the new Claude (Pro and Max first), no mode to pick: plan in any chat. Its calendar link is a connector.

Ask
New chatthenPaste the facts

If something's unclear, Claude asks. Still see Chat and Cowork? Use them as before.

Read
+thenConnectorsthenGoogle Calendar

Switch it on for this chat. Team or Enterprise: an owner enables it first.

Brake
Always allowNeeds approvalBlocked

By default, each action waits for your yes. Keep it so for the tools that create, change or delete events: in Customize, then Connectors.

ChatGPT

Work for a plan you want as a file. Calendars are apps, in Plugins.

Ask
WorkthenDescribe the outcome

Add “any files, constraints, and review criteria”. Chat works for a quick plan.

Read
PluginsthenGoogle CalendarthenInstall plugin

Connect your account if asked. Or Outlook Calendar. Then type @ and pick it in the chat.

Brake
Always askAllow read actionsAllow low-risk actionsAllow all actions

Allow low-risk actions is the default. Start with the first two. At work, your admin may set it.

Work and the calendar apps depend on your plan and workspace.

Gemini

Plan in a chat. Calendar comes with the Google Workspace app.

Read
@thenGoogle Calendar

Connect Google Workspace when it offers. Keep Activity must be on.

Keep
Export to Sheets

At the bottom right of a table: a new spreadsheet in your Drive.

Brake

Ask it to read only

It can also create and manage events. Move meetings yourself.

Work or school account: your admin must first allow connected apps.

Quick check · three questions

Did it stick?

  1. 1Two of the three people on a launch are away for a week in November. Where does that go?

    The answer: B It plans only around what it can see. Leave and other deadlines go in first.

  2. 2Before you share the plan, which question tests it best?

    The answer: A Owners you can check in the table yourself. Shake it in the chat before a real week does. Ask what's missing and what breaks first, too.

  3. 3Your calendar connector is on, and the plan says you're free on the 12th. Now what?

    The answer: C It drafts; you own it. The plan goes out under your name, so the dates get your eyes.
0 of 3 answered
A week, not a projectSide note
The same moves plan your week: the goal, your fixed meetings, three must-dos with a day each, and what you'd drop if Wednesday goes.
What waits for whatSide note
A step that can't start until another ends depends on it. When one slips, everything waiting on it slips too. That's why the plan shows the arrows.
Keep the plan aliveSide note
For a long project, keep the plan and its files together: a project in Claude or ChatGPT, a notebook in Gemini. When things change, ask the three questions again.
Sources, checked 18 Oct 2026Source

Product details as of Oct 2026, each checked on the vendor's own page on 18 Oct 2026. Recheck by 18 Nov 2026. The examples in the pictures are made up for this lesson.

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Turn a goal into a tested plan with owners and dates.

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