Executive Assistant Initialize Prompt

I want you to set up this project folder as my personal executive assistant / second brain in Claude Code. You’re going to do this in 3 phases. Complete each phase fully before moving to the next.

Phase 1: Create the folder structure

First, initialize a git repo in this folder if one doesn’t exist already.

Then create the following template structure. Don’t put any content in the files yet – just create the skeleton with placeholder files where noted.

CLAUDE.md                           # Main brain file (we'll fill this in Phase 3)
CLAUDE.local.md                     # My personal overrides (git-ignored)
.gitignore                          # Ignore .env, CLAUDE.local.md, settings.local.json
.claude/
  settings.json                     # Empty JSON object for now: {}
  rules/                            # We'll add rule files in Phase 3
  skills/                           # Empty -- we'll build skills over time
context/
  me.md                             # About me (filled in Phase 3)
  work.md                           # My business/work details (filled in Phase 3)
  team.md                           # My team (filled in Phase 3)
  current-priorities.md             # What I'm focused on right now (filled in Phase 3)
  goals.md                          # Quarterly goals and milestones (filled in Phase 3)
templates/
  session-summary.md                # Template for session closeout
references/
  sops/                             # Standard operating procedures (empty for now)
  examples/                         # Example outputs and style guides (empty for now)
projects/                           # Active workstreams (empty for now)
decisions/
  log.md                            # Decision log (append-only, empty for now)
archives/                           # Completed/outdated material (empty for now)

For empty directories, create a .gitkeep file inside them so git tracks them.

For templates/session-summary.md, use this starter template:

# Session Summary


**Date:**
**Focus:**


## What Got Done
-


## Decisions Made
-


## Open Items / Next Steps
-


## Memory Updates
- Preferences learned:
- Decisions to log:

For decisions/log.md, use this starter:

# Decision Log


Append-only. When a meaningful decision is made, log it here.


Format: [YYYY-MM-DD] DECISION: ... | REASONING: ... | CONTEXT: ...


---

For .gitignore:

.env
CLAUDE.local.md
.claude/settings.local.json
node_modules/

For CLAUDE.local.md:

# Local Overrides


Personal preferences and overrides that don't get shared via git.
Add anything here that's specific to your local setup.

Phase 2: Ask me onboarding questions

Before filling in the context files, rules, and CLAUDE.md, interview me. Ask these questions one section at a time. Don’t dump all questions at once – go section by section and wait for my answers before moving on.

Section 1: About You

• What’s your name?
• What’s your role/title? (e.g., CEO, freelancer, content creator, developer)
• What’s your timezone?
• In one sentence, what do you do?
• What’s your #1 priority – the thing everything else should support?

Section 2: Your Business / Work

• What’s your company or business called? (or describe your work if you’re not a business owner)
• What are your products, services, or revenue streams? (List each with a one-liner)
• Roughly how much revenue does each generate? (optional, but helps me prioritize)
• What tools do you use day-to-day? (ClickUp, Notion, Slack, Google Workspace, etc.)
• Do you have any MCP servers already connected to Claude Code? (If you don’t know what this means, just say no)

Section 3: Your Team

• Do you have a team? If yes, how many people?
• Who are the 2-3 key people I should know about? (name, role, when to loop them in)
• Where does your team communicate? (ClickUp, Slack, etc.)
• What’s your biggest pain point with managing your team?

Section 4: Priorities, Goals & Projects

• What are the 3-5 things you’re most focused on right now?
• Are there any deadlines or time-sensitive items I should know about?
• Do you have quarterly goals or milestones you’re tracking? (If yes, list them. If you don’t do formal goals, that’s fine – your priorities above will work.)
• What active projects or workstreams are you managing right now? (These are specific initiatives, not ongoing responsibilities. E.g., “launching a new course”, “hiring a VA”, “redesigning the website”)

Section 5: Communication Preferences

• How do you like information presented? (bullet points, detailed paragraphs, etc.)
• Any writing pet peeves? (e.g., “never use emojis”, “no em dashes”, “keep it under 3 sentences”)
• What tone do you want internally (casual, professional, etc.)?
• What tone do you want for external/public-facing content?

Section 6: What Do You Want Help With?

• What are the recurring tasks that eat up your time? (List as many as you want)
• What would you hand off to an assistant first if you could?
• Are there any specific workflows you want to automate or templatize?

Phase 3: Build out the files

Based on my answers, fill in all the files:

Context files

• context/me.md – My profile based on Section 1 answers
• context/work.md – My business/work details based on Section 2 answers
• context/team.md – Team structure based on Section 3 answers (if I have a team; if solo, note that and skip this file)
• context/current-priorities.md – Priorities from Section 4, dated today
• context/goals.md – Quarterly goals and milestones from Section 4. If no formal goals, use their top priorities as informal goals. Date it with the current quarter (e.g., “Q2 2026”). Include a note at the top: “Update this file at the start of each quarter.”

Projects

If the user listed active projects in Section 4, create a folder for each inside projects/. Each project folder gets a brief README.md with:

• One-line description of the project
• Current status (active, planning, on hold)
• Key dates or deadlines mentioned

If no specific projects were mentioned, leave projects/ empty.

Rule files in .claude/rules/

Create rule files based on my communication preferences (Section 5). Suggested files:

• communication-style.md – Writing tone, formatting preferences, pet peeves
• Any other domain-specific rules that emerged from my answers (e.g., if I mentioned specific tool conventions, content guidelines, etc.)

Keep each rule file focused on ONE topic. Don’t create more than 3-4 rule files to start.

CLAUDE.md (the main brain file)

This is the most important file. Keep it UNDER 150 lines. It should contain:

1. One-line identity – Who you are to me (e.g., “You are [Name]’s executive assistant.”)
2. Top priority – The #1 thing everything supports
3. Context imports – Use @context/me.md, @context/team.md, @context/goals.md, etc. to reference files instead of repeating their content
4. Tool integrations – What tools are connected (ClickUp, etc.)
5. Skills directory – Point to .claude/skills/ and explain how skills work
6. Decision log – Point to decisions/log.md and explain append-only convention
7. Memory – Add a section explaining how memory works:
   • “Claude Code maintains a persistent memory across conversations. As you work with your assistant, it automatically saves important patterns, preferences, and learnings. You don’t need to configure this – it works out of the box.”
   • “If you want your assistant to remember something specific, just say ‘remember that I always want X’ and it will save it.”
   • “Memory + context files + decision log = your assistant gets smarter over time without you re-explaining things.”
8. Keeping context current – Add a brief maintenance section:
   • Update context/current-priorities.md when your focus shifts
   • Update context/goals.md at the start of each quarter
   • Log important decisions in decisions/log.md
   • Add reference files as needed
   • Build skills when you notice you’re repeating the same request
9. Projects – Point to projects/ and explain that active workstreams live there
10. Templates – Point to templates/
11. References – Point to references/
12. Archives rule – Don’t delete, archive

Do NOT put communication style rules in CLAUDE.md – those go in .claude/rules/communication-style.md.

Do NOT repeat context from the context files – just import them with @.

Do NOT include a “Session Start Protocol” that tells Claude to read a bunch of files – the import system and rules handle that automatically now.

Skills directory

Leave .claude/skills/ empty. Don’t create any skills yet. Just make sure CLAUDE.md mentions that skills live there and explains the pattern:

• Each skill gets a folder: .claude/skills/skill-name/SKILL.md
• Skills are built organically as recurring workflows emerge
• Include a note about the answers from Section 6 (what they want help with) as a “Skills to Build” backlog in CLAUDE.md or a separate file

Final Step

After everything is created:

1. Show me a tree view of every file and folder you created
2. Show me a brief summary of what’s in each file (one line per file)
3. List the “Skills to Build” backlog based on my Section 6 answers – these are the workflows we’ll turn into skills over time
4. Show me this maintenance cheat sheet:

Keeping Your Assistant Sharp

• Weekly: Nothing required. Auto-memory handles daily learnings for you.
• Monthly: Glance at context/current-priorities.md. If your focus has shifted, update it.
• Quarterly: Update context/goals.md with new goals and milestones.
• As needed: Log decisions in decisions/log.md. Add reference files. Build new skills.
• Pro tip: If you want your assistant to remember something permanently, just tell it: “Remember that I always prefer X.” It will save it across all future conversations.

5. Create the first git commit with all the files
6. Ask me if I want to build any of those skills right now

Important Rules for You (Claude)

• Do NOT create any skills yet. The skills directory should be empty after setup.
• Keep CLAUDE.md UNDER 150 lines. If it’s getting long, you’re putting too much in it.
• Use @ imports (e.g., @context/me.md) in CLAUDE.md instead of repeating information.
• One rule file = one topic. Max 3-4 rule files to start.
• Ask onboarding questions ONE SECTION AT A TIME. Wait for my response before asking the next section.
• If I say “skip” or “I’ll fill that in later” for any section, create the file with a placeholder and move on.