Guide Library

Week 2 · Guide 5 of 5

Prompting

Write the Ask Your Boss Can Say Yes To

Field Guide

  • 20–30 minGuided walkthrough

When you need something approved, the way you ask shapes how fast you get an answer. Your agent asks you the questions your boss is likely to ask, drafts a short request that opens with the decision you need, then reads it the way your boss might, so you can fill the gaps before you send it.

You’ll leave with

A request in your voice for a decision you really need, ready to send, that opens with what you’re asking for and by when.

What You Need for This Guide

  • Something you need your manager or leadership to approve, and what you know about it so far.
  • Your approved AI tool, with your and, if you have it, your saved My Communication Style Guide.
  • The email, chat or memo where the request will go.

Build Your Communication Style Guide

Choose the tool you’re allowed to use

Your approved tool

The tool your company approved.

Pick your approved tool above to see the steps and screenshots for it.

Start guide
5 steps · At your own pace
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Standard Data rules for AI at work

Data Rules

Data rules for AI at work

Check with your IT Team before you paste any work data into an AI tool. Avoid names, account numbers, customer data, or anything sensitive without explicit permission from IT. If you aren't sure, redact anything sensitive and replace it with generic information. AI makes mistakes, make sure to fact check your agents outputs even if they sound right.

Before you start

  • Check with your IT teamAsk what your company allows before you put anything from work into an AI tool. Your company policy is the one that counts, and it is the one this library cannot see.
  • Use the tool your company approvedChatGPT, Claude, Microsoft 365 Copilot Chat and Gemini are all covered here. Use the one your company approved, not the one you like best.
  • Sign in with your work accountA work account keeps your chats inside the agreement your company signed. A personal account in the same product sits outside it.
  • No approved account yetFollow the steps with made-up example text, or on paper, until IT gives you one.

Never put this into an AI tool

  • Customer or personal detailsNo names, email addresses, phone numbers, home addresses or account numbers. That covers colleagues as well as customers.
  • Regulated recordsHealth, financial, HR and legal records stay in the systems built to hold them, unless IT has told you in writing that this tool may see them.
  • Passwords, keys and access codesNo credentials of any kind, yours or anyone else’s, and nothing that grants access to a system.
  • Anything under an NDA or not yet publicUnreleased plans, contracts, pricing and source code need clearance before they go near a chat window.
  • Anything your company policy prohibitsYour company’s rules win over anything in this library. If policy keeps something out of AI tools, it stays out, whatever a guide suggests.

Do this instead

  • Swap real details for placeholdersWrite “Customer A”, “[client name]”, “$X”. You get the same quality of answer, and you put the real details back yourself.
  • Describe the situation rather than pasting the documentMost of what an agent needs is the shape of the problem, not the file it arrived in.
  • Trim a file before you upload or paste itTake out the identifying columns and pages first, or work from a short extract.

Check the answer before you use it

  • Read it as if a colleague had drafted itAn agent states wrong things with complete confidence. Your name goes on the work, so the check is yours.
  • Say where the agent helpedFollow your company rule on disclosing AI assistance, especially in client-facing or formal work.

When you are not sure

  • Ask before you paste or upload, not afterA question to your IT team takes a minute. Cleaning up after a data incident takes a great deal longer.
  • When in doubt, leave it outIf you would not put it in an email to someone outside the company, keep it out of the chat.

On this guide

  • Choosing what to ask forDo not use this guide for a request about one person’s pay, performance, conduct or health, whether yours or a colleague’s. Describing someone by role does not hide who they are, so take it to your manager or HR directly. A request for staffing or overtime for a team is fine.
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Step

Choose your ask and name the decision

Pick something you need someone above you to approve, the kind of request that tends to sit in your drafts while you work out how to put it. For example:

  • Money for a tool, a subscription or equipment
  • Training, a conference or time to learn something
  • A change to a process or schedule, or more time on a deadline
  • Outside work, a request to a committee, such as a school or homeowners’ association

Nothing in mind? Send the prompt below in a new chat with your attached or pasted, or in its Project or Notebook. Replace the bracketed words in its What I’m looking for line with a request I need my manager or leadership to approve, answer its questions and pick a suggestion.

Find a task or decision
Using my Agent Profile and my answers, help me choose one small task to try or decision to think through. If my profile is missing from this conversation, ask me to attach or paste it before continuing. Do not assume I have a pending task or decision, or that it relates to a project in my profile.

What I'm looking for: [a task to try or a decision to make]

For now, help me identify and describe what I want to work on. Do not carry out the task, compare the decision's options, decide for me, or make a plan.

Ask me up to three short questions, one at a time, about work I need to get done or a choice I expect to face. If nothing is pending, ask about a recurring task or choice.

With each question:
- Offer two or three short suggested answers based on my role, responsibilities, priorities, or projects in my Agent Profile.
- Write these options directly in your response as a numbered list.
- Present them as possibilities for me to confirm, not tasks or decisions you assume I have.
- Include “Something else / none of these.”
- Let me choose a number, combine options, or answer in my own words.

Wait for each answer before continuing. Use my answer to shape the next question, and stop asking as soon as we have a clear task or decision I want to work on.

If we still have several possibilities, suggest up to three specific tasks or decisions of the kind I'm looking for, grounded in my profile and answers. Show them as a numbered list. Describe each in a sentence or two, including what I would give you, what you could help me produce or compare, and what I would still need to check or decide myself. Keep them small enough for me to try. Include “Something else / none of these” alongside those choices. Ask which one I want to work on, and wait for my choice.

Once I choose, write one sentence in my voice naming only the task I selected or the decision I want to think through. Use the details I confirmed in my answers; do not add details from my profile to the description unless I confirmed their connection to this task or decision. Omit details I have not provided rather than making a statement about them. For a decision, describe what needs to be decided without making the decision.

Return that description in one copyable code block. Include only the selected task or decision description. Then stop and wait for my next prompt.

If I have already named a clear task or decision I want to use, skip the questions and options and give me that description directly.

Use only facts in my profile and answers. Do not invent details, commitments or authority. If details should not be shared, let me describe the general pattern instead, and keep missing details uncertain.

Now write one sentence that names the decision you need, in the form approve what, by when. A request without a clear decision tends to get “let’s discuss” instead of a yes. If you can’t write it yet, ask yourself what you want your boss to reply.

Under it, jot down what you already know: why you need it, what it costs in money or time, what else you considered, and what happens if nothing changes. Rough notes are fine, and so are gaps, because your agent asks about them next. Check the data rules before you paste your notes into a chat.

Step

Let your agent ask what your boss might ask

  1. Open a new chat where your agent can see your and Communication Style Guide. If they’re saved in your agent’s Project or Notebook, start the chat there. Otherwise, attach or paste both files.

  2. Copy the prompt below and fill in its brackets: your decision sentence, who decides, described by role with what they care about if you know it, where the request will go and your notes. Add a setting from your My Voice Dial if you’ve built one. Then send it.

  3. The agent asks up to five questions, one at a time, about what your decision-maker would want to know that your notes don’t cover. Answer each one the way you’d answer your boss in the hallway, describing people by role rather than by name. Every question you answer now is one less round of back-and-forth after you send the request. After your last answer, the agent writes the draft and lists what it marked [CHECK] and any claim that rests on your opinion.

Step

Read the draft the way your boss will

  1. A busy decision-maker often decides from the first two sentences whether to deal with a request now, so read only those first. Can you tell what’s being asked, and by when? If not, ask the agent in the same chat to rewrite the opening so it says both.

  2. In the same chat, copy the prompt below and replace the bracket with who decides. In this read-back, the agent reads your request as that person and tells you what would get a yes, a no or a “not yet”.

  3. Compare the reader’s one-sentence summary with your decision sentence from step 1. If they don’t match, the opening needs work. The reasons for a no and the follow-up question show what to add, but add only what’s true.

Step

Make the fixes and check every fact

  1. In the same chat, ask for the specific changes you want, in your own words, such as “Add one sentence comparing the repair quote with the price of new.” Skip any suggestion that doesn’t fit your situation.

  2. Fill in each [CHECK]. Then check every number, date and claim against your notes and your answers, including totals the agent worked out and any claim it listed as resting on your opinion. Keep an opinion only if you’d say it to your boss yourself, and take out anything you can’t stand behind. Your name goes on the request.

  3. Reread the first two sentences after your edits. They should still say what you need decided and by when.

Step

Send it yourself and save the prompts

  1. Copy only the final request, not the lists under it, into your email, chat or memo and send it yourself. If the agent suggested a subject line, check that it names the decision.

  2. Copy both prompts from this guide into a note or file in My Agent Files, or another folder you can find again. Edit your saved copies to fit your work. If you usually ask the same person, put their role and what they care about into the Who decides line for good.

The next time a request sits in your drafts, start with the decision sentence and these two prompts.

Write the Ask Your Boss Can Say Yes To

Confirm your result

Confirm the outcomes below to finish this guide.

Final checks

You have a request in your voice whose first two sentences say what you need decided and by when, and every number and date in it matches your notes and your answers.

Your request answers the follow-up question the read-back raised, or says when you’ll have the answer.

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Week 2 field guides

Keep exploring when you’re ready

Revisit this week’s guides whenever they fit something you want to do.