Week 1 · Thursday hack

Let AI Interview You

Walk away with an interviewed Personalized AI Profile, and see the same request get clearly better after the interview.

  • Aug 18, 2026Last verified
  • 4 platformsChatGPT, Claude, Copilot, Gemini
  • 30–40 minTimed hack

Download Guide Edit copy

Step

Step 1: Check the thin profile

New Chat. Attach Tuesday's file. Paste the sample request. Keep the answer. This is the weak baseline. Same words come back in step 5, after the interview. Paper path.

1. Open a new Chat

Stay on Chat — not Work, not Cowork, not Code. If the product is Gemini, use Gemini Enterprise. If the product is Copilot, use Microsoft 365 Copilot Chat. Do not create a Project or an Agent.

2. Attach the existing profile

Attach the Personalized AI Profile from Tuesday to this chat. A new Chat does not already have it.

3. Paste this sample request

Paste the block below. Keep the answer. You will paste these exact words again after you save the interviewed file.

You do

Open a new Chat, attach Tuesday's Personalized AI Profile, then paste this block.

AI does

Answers from the thin first-pass file. Often generic.

Sample request
Propose a one-page outline for the type of document I have to produce regularly. Match audience, cadence, and what I am not allowed to include. If the profile is too thin, say what you cannot yet decide.

Step

Step 2: Start the interview

A second new Chat. Attach the same Tuesday file. Paste the interview prompt.

1. Open a second new Chat

Do not continue the before-check thread. Open a second new Chat. Stay on Chat — not Work, not Cowork, not Code. If the product is Gemini, use Gemini Enterprise. If the product is Copilot, use Microsoft 365 Copilot Chat.

2. Attach the same file and paste the interview

Attach the same Tuesday Personalized AI Profile. Then paste the interview prompt in that chat.

You do

Open a second new Chat, attach the same Tuesday file, then paste this block.

AI does

Interviews you one question at a time, with options plus Other, from what is already in the file.

Interview prompt
You have my Personalized AI Profile attached.

Treat me as a new coworker who just received this file. Interview me so you can fill the gaps a capable new employee would still need in order to actually help. Use what is already in the attached file. Do not start a new file. Do not run FIRST SETUP CHECK now.

Ask one question at a time. Wait for my answer before the next question. Never send a list of questions. Never ask ten questions at once.

Each question must:
- Target a gap in the attached file that would change the help: role, recurring deliverables, audience, cadence, constraints, or terminology.
- Present a short set of options based on what is already in the file, plus Other so I can type something else.
- Stay simple. First-question shape: "What types of documents do you have to produce regularly?" with options such as PowerPoints, Word documents, Excel, Other, and a way for me to type whatever I want. Then the next question. If the file already names likely options, use those. If it does not, use simple work-document options like the example.

Do not ask for, or accept, passwords, credentials, protected customer information, private employee data, confidential financial details, regulated information, or anything an organization would not allow in an AI tool. If a useful question would require that, skip it.

Do not invent company, customer, employee, product, pricing, policy, or project facts. If you would have to guess, leave the line as it is.

Add only working context that would change the help. Do not add extra biography. Do not fill every blank. Do not invent a new outline, new section names, or a personal biography dump. Keep the same headings and section order as the attached file, including FIRST SETUP CHECK.

Keep going only until the gaps that would change the help are filled. Then stop interviewing.

After my last answer, output the complete updated Personalized AI Profile as plain text I can copy and save over my existing file. No preamble. No interview questions in that output. Do not claim you attached a file.

Start now with your first question.

Step

Step 3: Answer the questions

One question at a time. Detail that is allowed. Never-enter stays out. Answer every question with as much detail as you can, without giving information you are not allowed to put in an AI tool. Relevance does not override permission. If a question would need a name, a figure, or a record you cannot share, answer with the pattern instead — the type of document, the kind of audience, the cadence — or skip that question. Stay in this same interview Chat until it returns the updated file.

It asked for restricted or sensitive facts

Next Do not answer that question with restricted information. Reply: never add passwords, credentials, protected customer information, private employee data, confidential financial details, or regulated information. Ask the next allowed question. If you already provided restricted information, follow your company's incident process.

Step

Step 4: Save the updated file

Copy the returned file. Save over your existing Personalized AI Profile.

1. Copy and save over the file

At the end of the interview, the assistant should return the full updated Personalized AI Profile as plain text. Products do not reliably attach a file back. Do not wait for an attachment. Copy the returned text and save it over your existing Personalized AI Profile on disk. The returned file must keep the same headings and section order as Tuesday's file, including FIRST SETUP CHECK. If it invented a new outline, ask it to return the file again with the attached headings, in that order.

2. Scan added lines

Read the returned file before you save. Both questions still apply to every added line: 1. Does the assistant need this to help with the work? 2. Am I allowed to provide it? If either answer is no, delete that line. Relevance does not override permission. Do not keep extra biography, filled blanks, or guessed company facts.

It invented company, customer, or project facts

Next Delete guessed lines. Reply: do not invent company, customer, employee, product, pricing, policy, or project facts. If you would have to guess, leave the line as it is. Return the file again, same headings and order as the attached file. Then save that version.

Step

Step 5: Check the interviewed profile

A third new Chat. Attach the updated file. Paste the same sample request.

1. Open a third new Chat

Open a third new Chat. Do not continue the interview thread. Do not reuse the before-check thread. Stay on Chat — not Work, not Cowork, not Code. If the product is Gemini, use Gemini Enterprise. If the product is Copilot, use Microsoft 365 Copilot Chat.

2. Attach the updated file and paste the sample

Attach the updated Personalized AI Profile. Paste the exact same sample request as step 1.

You do

Open a third new Chat, attach the updated file, then paste this block. Same words as step 1.

AI does

Answers from the interviewed file. Should be clearly more specific.

Sample request
Propose a one-page outline for the type of document I have to produce regularly. Match audience, cadence, and what I am not allowed to include. If the profile is too thin, say what you cannot yet decide.

Done when

You should see a clearly better answer. That difference should only work because the interview happened.

Done when

You have saved the interviewed file over your Tuesday copy, and the same sample request is clearly better with that file attached.