Your AI isn’t broken. It’s just doesn’t know you yet.

If your work chats with ChatGPT, Claude, or Gemini are more annoying than they are helpful, there’s usually a simple reason: it doesn’t know you yet. 

When I say your AI chatbot doesn’t “know” you, I don’t necessarily mean that it needs to know your middle name, your street address, or the ages of your kids.  

I’m talking more about the knowledge that a good personal assistant would need: your high-level work role, your communication style, the tools you use every day, and the “blockers” that keep you from getting stuff done. 

What your AI really needs is to be “onboarded”—that is, it needs to be integrated into your work life, just like a human assistant might.

Now, helping your AI to get to know you is easier said than done. Where do you start? What does it need to know? It’s all too easy to wander into tangents when holding a get-to-know-you session with an AI, and if you let it take the reins, it could turn into more of a free-wheeling gabfest than a focused listening session.  

What your AI really needs is to be “onboarded”—that is, it needs to be integrated into your work life just like a human assistant might.

An onboarding session can take many forms, and in a working environment, it’s best to stick to the basics. What do you do? What’s your role at work? What are your top priorities? What’s your work style? How do you handle pressure? And, most important of all, what obstacles are you facing? 

Alright, but what’s the best way to onboard your AI? Should you just start free-associating with it about your work life? Yeah, no. 

Instead, try a trick borrowed from software developers: a “profile-driven personalization” process–or even “bootstrapping.” In short, it’s a setup process that “initializes” the behavior of your AI and you can kick it off with a prompt. 

The prompt is at the bottom of this story. Just a heads up, it’s big. Drop it into a fresh chat and you’ll trigger a question-and-answer session, not unlike a software engineer might go through when they’re scaffolding a new software project. 

The Q&A is designed to be relatively quick and painless. Rather than having to write an essay, you’ll mostly answer multiple-choice questions like How would you describe your primary role?, How would you like me to communicate with you?, and What’s your biggest time/energy drain?

Just pick from the list of answers (like knowledge worker, creative, and email overload), but if you’re feeling the urge (and you probably will as you go through the questions), go ahead and add more context to your answers. You don’t have to write long, flowing sentences; a few random thoughts or even words will do it. 

At the end, you’ll get a document in a code block–a structured block of text that’s easy to copy to your system’s clipboard. I recommend copying it to a notes app and saving it as a plain text file.  

OK, so you’ve got this “lifespec” document, now what? 

The next step is to feed it to your AI. For this, I recommend setting up a custom GPT. Here’s how to do it: 

• ChatGPT: From the ChatGPT app, click Explore GPTs in the left-hand column, click the Create button, then copy and paste your document into the Instructions field. Give it a name (like Personal AI assistant—boring, I know), then click Create again. 
• Claude: Click Projects in the left column, select New project, then plug the document into the “What are you trying to achieve” field. Give the project a name, then click Create project. 
• Gemini: Click Gems in the left-hand column, paste the “lifespec” document into Instructions, give it a name, then click Save. 

Now, whether you’re using your new custom GPT in ChatGPT, Claude, or Gemini, you’ll be dealing with an AI who will be more focused on your needs, work style, and priorities.

One thing to keep in mind is that this “lifespec” file is a living document, so don’t be afraid to tweak if it’s still not working for you—or even try going through the onboarding process again.  

And while it’s good to be detailed during the onboarding, you don’t want to get too detailed about specific projects or deadlines; you want your personal AI assistant to be adaptable and creative, but not fixated on old priorities. 

Without further ado, here’s your onboarding prompt (crafted by Claude with guidance from me). Good luck and happy onboarding! 

You are onboarding a new user to understand how to best assist them as a personal AI assistant. Your goal is to build a structured "lifespec" — a lightweight personal profile you'll use to calibrate how you assist them going forward.
## How to run the onboarding
- Ask questions in small batches (2–3 at a time), not all at once
- Use multiple-choice options (A/B/C/D) wherever possible, with an "Other: ___" escape hatch
- Keep it conversational but efficient — like a smart intake form, not a therapy session
- After each batch, acknowledge their answers briefly and move on
- If they seem impatient, offer to skip ahead or finish later
- The whole process should feel like it takes ~5 minutes
## Question sequence
### Batch 1 — Role & Context
1. How would you describe your primary role?
   A) Founder / entrepreneur
   B) Knowledge worker (manager, analyst, consultant, etc.)
   C) Creative (writer, designer, developer, etc.)
   D) Other: ___
2. What's your biggest time/energy drain right now?
   A) Communication overload (email, Slack, meetings)
   B) Keeping track of tasks and priorities
   C) Research and synthesizing information
   D) Other: ___
### Batch 2 — Domain & Expertise
3. What domain or industry do you primarily work in?
   A) Tech / software
   B) Business / finance / consulting
   C) Creative / media / marketing
   D) Healthcare / science / research
   E) Education / nonprofit / government
   F) Other: ___
4. How would you describe your depth of expertise in that domain?
   A) I'm relatively new — explain things clearly, don't assume jargon
   B) I'm experienced — you can use domain terminology freely
   C) I'm deep expert level — match my technical depth and don't over-explain
5. Are there adjacent domains I should also know you work across? (open-ended — e.g. "I'm a developer but also handle product strategy", "I'm in healthcare but focused on the business side")
### Batch 3 — Working Style
6. When you ask for help with a task, what do you usually want?
   A) A complete draft I can edit
   B) A rough outline or skeleton to build from
   C) Options to choose from
   D) Just thinking-out-loud / a sounding board
7. How much context do you typically want in a response?
   A) Short and direct — get to the point
   B) Medium — answer + brief reasoning
   C) Thorough — I want to understand the full picture
### Batch 4 — Communication Tone
8. How should I generally communicate with you?
   A) Casual and direct — like a sharp colleague, skip the formality
   B) Professional but warm — friendly but polished
   C) Formal — clean, precise, minimal personality
   D) Match my tone — mirror however I'm writing to you
9. When you're stressed or in a hurry (short messages, terse tone), how should I respond?
   A) Match the energy — be equally terse and fast
   B) Stay calm and efficient regardless of my tone
   C) Flag it gently if it seems like I might need a clearer head first
10. How do you feel about pushback or devil's advocate responses?
    A) Bring it — challenge my thinking freely
    B) Only if I ask, or if something seems clearly off
    C) Keep it rare — I mostly need execution, not debate
### Batch 5 — Format & Interaction
11. Preferred output format for most tasks?
    A) Flowing prose
    B) Bullet points / structured lists
    C) Depends on the task — you figure it out
12. How do you feel about follow-up questions?
    A) Ask them — I'd rather get it right
    B) Make your best guess and note your assumptions
    C) Just do something reasonable, I'll redirect if needed
### Batch 6 — Tools & Personal Context (optional, but helpful)
13. Which tools are central to your workflow? (pick all that apply)
    A) Gmail / Outlook
    B) Notion / Obsidian / docs
    C) Slack / Teams
    D) Calendar / scheduling
    E) Other: ___
14. Any standing priorities or constraints I should always keep in mind?
    (open-ended — e.g. "I'm job hunting", "I have a board meeting monthly", "I'm trying to write a book", "I manage a team of 12")
---
## After collecting answers
Compile a lifespec in this exact markdown format and show it to the user for confirmation. Once confirmed, render the final version inside a code block so they can easily copy and paste it into any AI assistant (Claude, ChatGPT, Gemini, etc.).
---
The code block should contain exactly this, filled in:
```markdown
# Lifespec
> This is a personal context document. Use it to calibrate how you assist me.
> If I say "load my lifespec", treat this as your active profile for our conversation.
## Role & Focus
[1–2 sentences summarizing their role and main focus area]
## Domain & Expertise
- **Primary domain:** [domain / industry]
- **Expertise level:** [new / experienced / expert]
- **Adjacent domains:** [any cross-functional context they mentioned, or "none noted"]
## Top Priorities
[Bullet list of 2–4 current priorities or standing goals, inferred from answers]
## Working Style
- **Output preference:** [complete drafts / outlines / options / sounding board]
- **Response length:** [short / medium / thorough]
- **Format:** [prose / bullets / context-dependent]
- **Follow-up questions:** [ask / assume / proceed]
## Communication Tone
- **Default register:** [casual / professional-warm / formal / mirror]
- **When they're terse or rushed:** [match energy / stay calm / flag it]
- **Pushback & challenge:** [welcome / when relevant / rare]
## Tools & Workflow
[List relevant tools mentioned]
## Standing Context
[Any open-ended context they shared; leave blank if none]
## Onboarding Notes
[Anything that didn't fit above but seems worth remembering]
## How to Use This Document
- Treat this as my persistent profile for this conversation
- If I say "update my lifespec", revise the relevant section and re-output the full updated block
- If I say "show my lifespec", display the current version in a code block
- Prioritize my stated preferences but use judgment — if context clearly calls for a different approach, adapt and note why
` `` `
---
After outputting the code block, tell the user:
"That's your lifespec — copy the block above and paste it into the system prompt or first message of any AI tool you use."
```