---
id: prj-plan-with-clarifying-questions
schema: project/1
layer: garden
title: Let AI ask before it plans
outcome: A plan for a real piece of work that fits your situation on the first or second try, because the details that were in your head made it into the request.
roles: [team lead, programme coordinator, event organiser, project manager, anyone planning work for others]
time_box: 20 minutes
tool_access: Any general AI chat assistant (free tier is fine). Being able to edit a sent message helps but isn't required.
practises: [cmp-frame-the-outcome, cmp-describe-the-task, cmp-steering]
concepts: [con-clarifying-questions, con-context-engineering, con-prompting, con-prompt-engineering]
skills: [frame-the-problem, build-brief]
resources: [res-anthropic-prompt-design-intro, res-openai-prompt-best-practices, res-google-workspace-gemini-prompting-guide]
source:
  claim: Adding "ask me clarifying questions before you begin" to a request shows you which context you left out. Answering those questions, by editing the original request, gives a noticeably better fit than starting over.
  evidence: Inspired by the context lesson in WDAI's AI Basics course. The evidence is WDAI's experience teaching it to beginners, not a study.
  limits: The questions a tool asks vary between tools and between runs, and some won't matter for your task. This card doesn't show that the plan is correct, only that it fits your request better.
origin:
  kind: ai-proposed
  by: "seed agent 2026-10-16"
  rationale: Rewrites the AI Basics clarifying-questions exercise for a work setting and adds a check, a contradiction test and a reflection.
---

## Why this matters

"Plan a half-day offsite for my team" sounds clear to you, because you already know the team size, the budget, who works remotely and what the day is for. The AI doesn't. It fills each gap with a guess and gives you a plan that looks finished but fits someone else's team. Asking it to question you first shows you exactly which details were missing.

## Smallest useful build

Two versions of the same plan: one from your bare request, one after you've answered the AI's questions. Comparing them shows you which details changed the result. It takes about 20 minutes.

## Sample inputs

Use something you really have to plan: a team offsite, a programme launch, an onboarding week, a volunteer day. If you don't have one, use this:

```text
Plan a half-day offsite for my team.
```

Details hidden in that sentence include what the day is for, how many people, who joins remotely, budget, location, date, accessibility needs and what has to come out of it.

A household version works too. "Give me three easy weeknight dinners" leaves out how much time you have, how many people, diet, budget and equipment, so "easy" could mean almost anything.

## Steps

1. **Write your request and your own list.** Write the one-line request. Then, on paper or in a note, list the three to five details you think matter most. Keep that list away from the AI for now.

2. **Ask it to question you first.**

   ```text
   Plan a half-day offsite for my team. Ask me clarifying questions before you begin. Don't write the plan until I've answered.
   ```

   Compare its questions with your list. Circle any question you hadn't thought of.

3. **Answer the questions that matter and edit your original message.** Skip questions that don't change anything. Add your answers to your first message (most tools let you edit it and run it again) instead of opening a new chat.

   ```text
   Plan a half-day offsite for my team. Purpose: agree on next quarter's three priorities. 9 people, 3 joining by video. Budget $600 including lunch. Must be step-free. Output: a timed agenda and a one-paragraph note to the team. Don't add activities beyond what fits in four hours.
   ```

4. **Put the two plans side by side.** Note which of your answers moved the plan most, and which made no difference.

## Check it

- At least one question surfaced a detail you hadn't listed in step 1.
- Every answer you gave shows up in the second plan.
- The second plan contains nothing you didn't ask for. If it added extras, cross them out.

## Break it

Give an answer that contradicts your request, such as "budget is $0" while also asking for catered lunch. Does the AI point out the conflict and ask which one wins, or does it pick one without telling you? If it picked, ask it to list every assumption it made.

## Reflect

- Which detail was so obvious to you that you never thought to say it?
- Next time, which two questions could you answer before anyone asks?

## Next iteration

Use the same request with a different kind of plan, such as a launch checklist. Keep the details that keep coming up as a short checklist you add to future requests, so you're asked fewer questions each time.