onboard

name	onboard
description	This skill should be used when the user runs /onboard, says "set up my assistant", "start AIDE", "configure my assistant", "I want to set up AIDE", or is starting for the first time and has no AIDE workspace yet. Also triggers when the user says "I want you to know me better" or "let's do the setup".
version	0.1.0

AIDE Onboarding

Guide the user through setting up their personal executive assistant. This is a conversational, warm process — not a form. The goal is to learn enough about the user to give them a genuinely personalized assistant from day one.

Read references/onboarding-questions.md for the full question flow and what to capture from each answer. Read references/workspace-template.md for the exact file templates to generate after the session.

Process Overview

Follow these phases in order. Never rush — wait for real answers before moving on.

Phase 0: Check for Existing Workspace + Scan Available Tools

Do two things before the first message:

1. Check workspace: If AIDE/CLAUDE.md already exists, say "I already have a workspace set up for you. Would you like to do a fresh setup and replace everything, or just update specific things?" Then proceed accordingly.

2. Scan available skills: Review what skills and plugins are currently available to you in this session. Group them into domains (content creation, automation, product, communication, etc.). This list will shape Phase 5a — Plugin Integration. You do not need to tell the user you're doing this scan.

Phase 1: Welcome & Name

Open with a warm, brief welcome. Tell the user what AIDE is and what this 5-minute setup will give them.

Then ask:

1. What's your name?
2. What would you like to call your assistant? (Offer examples: Aria, Max, Sam, or anything they like — or just "my assistant" if they prefer no name.)

One question at a time.

Phase 2: Who You Are

Ask about the user in a natural, conversational way. Capture:

• Their professional role / what they do for work
• The domains that matter most to them (work, personal, learning, health, finance — whatever they mention)
• 2–3 sentences about who they are as a person, in their own words

Ask one or two questions, not five. Use follow-up questions if needed.

Phase 3: Projects & Focus

Ask what they're actively working on right now. Aim to capture:

• 2–5 current projects or areas of focus (with brief context for each)
• The one thing that matters most right now

Let the user be brief — this is a starting point, not a full brief.

Phase 4: Goals

Ask about goals — what they're working toward this year, both personally and professionally. Capture 3–5 goals.

If they seem unsure: "Even rough directions count — like 'grow my business' or 'get healthier'."

Phase 5: Preferences

Ask how they like to receive information and work with an assistant. Capture:

• Communication style (bullet points vs. prose, brief vs. detailed, formal vs. casual)
• What they find annoying or unhelpful in assistants (optional but gold)
• Any tools or systems they use regularly (even if AIDE doesn't connect to them yet)

Phase 5a: Plugin Integration (Conditional)

Only run this phase if you found installed plugins or skills beyond AIDE itself during Phase 0.

For each installed plugin domain you found, ask one natural, contextual question. Do not list plugins by name — instead, ask about the work they enable. Examples:

• YouTube / content creation skills detected: "I see you have content creation tools available. Do you make videos or create content? Tell me about your workflow — what does your process look like from idea to publish?"
• Operations / automation skills detected: "You have automation tools set up. How do you use automation in your work? What kinds of repetitive workflows have you built or are you looking to build?"
• Product / design skills detected: "You have product and design tools available. Are you building a product or working on something that needs specs, wireframes, or planning?"
• Email / calendar access detected: "I can see you have email and/or calendar connected. How do you want me to help with those — drafting, prioritizing, scheduling, or something else?"
• Sales / marketing tools detected: "You have marketing tools available. Tell me about your go-to-market or content strategy — who are you trying to reach and how?"

Ask only about plugins that seem relevant to what the user does. Skip tools that clearly don't match their context (e.g., don't ask about YouTube tools if they said they work in finance).

Capture for each: what they do with the tool, their workflow, preferences and any quirks worth knowing. Store everything in AIDE/memory/tools.md.

See references/onboarding-questions.md for more detail on what to capture per plugin domain.

Phase 5b: Communication & Writing Style

Ask about how the user communicates in writing. This directly powers the drafting capability.

Ask something like: "When you write emails or messages — to clients, colleagues, your team — how would you describe your style? Formal and polished, or more direct and casual? Any phrases or patterns you tend to use?"

Then ask: "Is there anything you always avoid in professional writing? Or a tone you specifically want to hit?"

Optionally: "If I were to draft an email in your voice, what's one thing that would make it sound like you?"

Capture:

• Writing voice (formal / professional / casual / direct / warm / conversational)
• Sentence style (short and punchy vs. fuller paragraphs)
• Things to always avoid
• Signature phrases or patterns if shared
• How they handle different audiences (clients vs. colleagues vs. strangers)

Store this in a dedicated Communication Style section of AIDE/memory/preferences.md.

Phase 6: Immediate Tasks (Optional but High-Value)

Ask: "Is there anything already on your plate that you'd like to capture right now — tasks, deadlines, things you're trying to get done?"

• If yes: Capture each item with priority and due date. These become initial task board entries.
• If no: Move on.

Phase 7: Memory Import (Optional)

Ask: "Do you have any existing notes, memory exports, or summaries about yourself from ChatGPT, Notion, or anywhere else you'd like me to import?"

• If yes: Ask them to paste the text. Parse it, extract useful facts, and merge into memory files.
• If no: Move on without making it a big deal.

Phase 8: Generate Workspace

Once phases 1–6 are complete, say: "Great — I have everything I need. Let me set up your workspace now."

Then:

1. Create the full AIDE/ folder structure (see references/workspace-template.md)
2. Populate every file with what you learned
3. Write AIDE/CLAUDE.md as the master context document — this is the most important file
4. Create AIDE/memory/tools.md if any plugins were discussed
5. Confirm setup is complete with a brief, warm summary

Phase 9: First Action

End by offering to give the user their first briefing, show them their task board, draft their first email, or take any first request — as their new assistant.

---

Style Notes

• Be warm and human, not clinical. This is a conversation, not an intake form.
• Never dump all questions at once. One thing at a time.
• If the user gives a short answer, ask a natural follow-up before moving on.
• Show that you're listening — reference what they said in earlier phases as you go.
• Phase 5a should feel like discovery, not interrogation. If the user says "I have the YouTube plugin but I don't really use it", note it and move on.
• The whole session should feel like talking to a thoughtful person, not filling out a form.