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Your AI Chief of Staff — a personal operating system starter kit that adapts to your role. No coding required.
A personal operating system powered by Claude. Strategic work management, meeting intelligence, relationship tracking, daily planning — all configured for your specific role. No coding required.
Companion to Episode 8 of The Vibe PM Podcast and the full blog post.
Total time: ~10 minutes. Three steps: install tools → get the code → tell it your role.
Pick one of these to get started:
| Option | Cost | What It Is |
|---|---|---|
| Cursor | Free tier works, or $20/month for Pro | An app with a built-in AI assistant (Claude). No separate Claude account needed. |
| Claude Code Desktop | Claude Pro $20/month | Anthropic's own app. Better experience — guaranteed self-learning hooks, automatic context loading. |
| Claude Code Terminal | Claude Pro $20/month | Same as Desktop but runs in Terminal (Mac) or PowerShell (Windows). |
You do NOT go to claude.ai and type commands. You need one of the apps above. Cursor is the easiest starting point. Claude Code (Desktop or Terminal) gives you a better experience with self-learning hooks — setup instructions for those are further down this page.
Not sure which? Start with Cursor — it's free and gets you running in minutes. You can add or switch to Claude Code later.
All installers walk you through setup with default options.
Why Python 3.10+? The MCP SDK (Model Context Protocol) requires Python 3.10 or newer. This powers the Work MCP server that enables task sync - when you check off a task in a meeting note, it updates everywhere automatically (person pages, project files, Tasks.md).
Mac users: If this is your first time using command-line tools, macOS will prompt you to install "Command Line Developer Tools" during setup. Click Install when prompted - it's safe and required. Takes 2-3 minutes.
You'll use something called a "command line" (or "Terminal" on Mac, "PowerShell" on Windows) during setup. This is a text-based way to give your computer instructions - think of it as typing commands instead of clicking buttons.
Don't worry if this feels unfamiliar. You'll copy and paste a few commands, press Enter, and you're done. Takes less than 2 minutes.
Want to verify everything's ready? Open your command line:
Cmd+Space, type "Terminal", press EnterWin+R, type "powershell", press EnterCopy and paste this line exactly as you see it, then press Enter:
git --version
You should see a response like: git version 2.x.x (any version number is fine)
If you see "command not found": Download Git from git-scm.com, install it, then close and reopen your command line and try again.
Now copy and paste this line, then press Enter:
node --version
You should see a response like: v18.x.x or v20.x.x (must be version 18 or higher)
If you see "command not found": Download Node.js from nodejs.org, install it, then close and reopen your command line and try again.
Finally, check Python:
python3 --version
Windows users: Try python --version if python3 doesn't work.
You should see a response like: Python 3.10.x or higher (3.11, 3.12, etc.)
If you see Python 3.9 or older: The MCP SDK requires Python 3.10+. Download and install a newer version:
If you see "command not found":
Why Python 3.10+ matters: It powers the MCP servers that sync tasks everywhere. Check off a task in a meeting note → it updates in your Tasks.md, person pages, and project files automatically. Python 3.9 and older won't work - you need 3.10 or newer.
That's the technical heavy lifting done. If you got through that, the rest is straightforward - just clicking buttons and answering questions.
Cmd+Shift+P (Mac) or Ctrl+Shift+P (Windows) - this opens a search bar at the tophttps://github.com/davekilleen/dex.git
Can't get this working? No problem:
dex-main)dex-main folderInside Cursor, you'll see a panel at the bottom (or go to View → Terminal). This is where you'll type commands.
Copy and paste this command and press Enter:
./install.sh
What's happening: This installs the automation that makes Dex work (task sync, career tracking, meeting intelligence). Takes 1-2 minutes. You'll see text scrolling - that's normal.
When it's done: You'll see your cursor blinking again, ready for the next command.
Your system Python stays clean: The installer creates a project-local virtual environment (.venv) inside your vault and installs all Python dependencies there — your system, Homebrew, or pyenv Python is never modified. No global installs, and no pipx needed.
⚠️ IMPORTANT: You're not done yet. Complete Steps 2B and 3 to finish setup.
Verify MCP servers: Cursor should automatically detect .mcp.json and enable the MCP servers. Look for the MCP icon in Cursor's bottom panel - you should see server names with green checkmarks.
If you see errors: The most common issue is Python dependencies not landing in Dex's virtual environment. Recreate it and reinstall — this keeps everything inside .venv and never touches your system Python:
python3 -m venv .venv
.venv/bin/pip install --upgrade pip
.venv/bin/pip install -r core/mcp/requirements.txt
Then restart Cursor.
If you use Google Calendar, you can have Dex show your real meetings when you run /daily-plan or ask "what's on my calendar today?" Two steps, one-time setup (Mac only):
Step 1 — Add Google to your Mac's Calendar app
Open the Calendar app (the one that came with your Mac). In the menu bar, click Calendar → Add Account… → choose Google → sign in with your Google account. Your Google events will sync into Calendar. Dex reads from this app, so once Google is here, Dex sees your meetings.
Step 2 — Let Cursor use your calendar
Open System Settings → Privacy & Security → Calendars. Turn Cursor on, then click Cursor and choose Full access (not "Add Only") so Dex can read your events. If macOS pops up asking "Cursor would like to access your calendars", click Allow.
That's it. The installer already set up the rest on Mac. Your meetings—including recurring ones like weekly 1:1s—will show on the correct days in Dex.
More detail and troubleshooting: Calendar_Setup.md (in your vault after setup).
On Windows? Calendar connection is supported on Mac via Apple Calendar. We don't have Windows instructions in this repo yet.
⚠️ IMPORTANT: Complete Step 3 now to configure your role - this is what makes Dex work.
If you see a popup asking to install "Command Line Developer Tools":
This only happens once. Future updates won't need this.
What if I accidentally clicked "Cancel"?
Run this command, then run ./install.sh again:
xcode-select --install
This means Python wasn't added to your PATH during installation.
Fix:
./install.sh againGit for Windows isn't installed.
Fix:
./install.sh againThe installer tries two methods automatically. If both fail, your pip version might be too old.
Fix (reinstall into Dex's virtual environment):
python3 -m venv .venv
.venv/bin/pip install --upgrade pip
.venv/bin/pip install -r core/mcp/requirements.txt
Windows:
python -m venv .venv
.venv\Scripts\pip install --upgrade pip
.venv\Scripts\pip install -r core/mcp/requirements.txt
If you see red error indicators next to MCP server names in Cursor:
"No server info found" error:
This means the Python MCP servers can't start. Most common fix — reinstall the dependencies into Dex's virtual environment:
python3 -m venv .venv
.venv/bin/pip install --upgrade pip
.venv/bin/pip install -r core/mcp/requirements.txt
Then restart Cursor completely (Cmd+Q and reopen, or File → Quit).
If you get "ERROR: Could not find a version that satisfies the requirement mcp":
Your pip is too old. Run the pip upgrade command above first, then try installing packages again.
"Command 'python' not found" error:
Your .mcp.json might have the wrong Python command. Open .mcp.json in your vault and change all instances of:
"command": "python"
to:
"command": "python3"
(Or vice versa on Windows - use whichever command works in your terminal)
Then restart Cursor.
Still not working?
Check the MCP server output:
If /daily-plan doesn't show your meetings, or your recurring meetings (e.g. weekly 1:1s) show on the wrong day or are missing:
.venv/bin/pip install -r core/mcp/requirements.txt, then restart Cursor.See Calendar_Setup.md for the full guide.
In Cursor, look for a chat panel (usually on the right side of the screen). This is Claude - your AI assistant.
Here's exactly what to do:
/setupJust type your answers like you're texting a colleague. Takes about 2 minutes total.
When it's done: You'll see confirmation that your workspace is configured. All folders, commands, and automation are now tailored to your specific role.
You just used Cursor to run setup. That works great for daily use.
There's also Claude Code - a more powerful option available via command line or Desktop app. Both give you guaranteed hooks (automatic behaviors that run deterministically, unlike CLAUDE.md which Claude might skip).
| Access Method | What You Get | Hooks? | Setup |
|---|---|---|---|
| Cursor | Easy, already working | No | Already done |
| Claude Code (command line) | Guaranteed hooks, persistent learning | Yes | 5 min install |
| Claude Code (Desktop app) | Guaranteed hooks, persistent learning | Yes | 5 min install |
What are hooks? Automatic behaviors triggered by events (session start, file read, etc.). They're deterministic - they ALWAYS run. Context loads guaranteed, learnings surface guaranteed, person details inject guaranteed.
Which to use?
Cursor:
Claude Code (command line or Desktop):
| Hook Example | What It Does |
|---|---|
| Session start | Loads Quarter Goals, Week Priorities, Strategic Pillars, Urgent Tasks automatically |
| Person context | When Sarah is mentioned in a file, her person page context injects automatically |
| Company context | When Acme Corp is referenced, company page details inject automatically |
| Mistake patterns | Surfaces active patterns so Claude avoids repeating them |
| Learning reminders | Prompts review when you have 5+ unreviewed learnings |
Command line vs Desktop: Same core capabilities, different interfaces. Command line is text-based terminal. Desktop is a GUI with visual session management and side-by-side diffs.
Bottom line: Cursor works great and is what most people use. Claude Code guarantees hooks run every time, making the system more intelligent and persistent. Many people use both - Cursor for heavy editing, Claude Code for workflows where reliability matters.
You're already set up with Cursor. If you want guaranteed hooks (automatic context loading every session), here are your two options:
If you prefer visual interfaces over command line, use the Desktop app.
Requirements:
Setup (2 minutes):
That's it. Hooks run automatically - session start context loads, person details inject when mentioned, mistake patterns surface.
Desktop app benefits:
For those comfortable working in Terminal (Mac) or PowerShell (Windows), Claude Code runs from the command line.
Requirements:
Step 1: Install
You can install from your system's native terminal or from within Cursor (easiest since you're already there).
Option A: Native Terminal/PowerShell
Mac - Terminal:
curl -fsSL https://claude.ai/install.sh | bash
Windows - PowerShell:
irm https://claude.ai/install.ps1 | iex
Option B: From Inside Cursor (Easiest)
Mac:
curl -fsSL https://claude.ai/install.sh | bash
Windows:
irm https://claude.ai/install.ps1 | iex
The installer automatically updates itself in the background to keep you current.
Step 2: Authenticate
In your terminal (native or Cursor's), run:
claude auth
This opens your browser. Log in with your Claude Pro or Max account.
Step 3: Start Claude Code
From your terminal, navigate to your Dex folder and run claude.
Note: Folder name depends on how you got the code:
dexdex-mainMac:
cd ~/Documents/dex # or dex-main if you downloaded ZIP
claude
Windows:
cd %USERPROFILE%\Documents\dex # or dex-main if you downloaded ZIP
claude
Need help? See official Claude Code setup docs for troubleshooting.
Which option? Desktop app for visual interface. Command line for those comfortable in Terminal/PowerShell. Both give you the same guaranteed hooks capability.
Non-engineers. Product managers, marketers, sales leaders, designers, executives, HR leaders, consultants, coaches, analysts — anyone who wants the same leverage from AI that technical people have had access to.
You don't need to know how to code. Just follow the setup above and talk to your AI assistant.
If you're an engineer: Share this with your non-technical colleagues. Distribute Dex across your organization to accelerate AI fluency adoption.
Want to share this? Point colleagues to the companion blog post for the full story. At the bottom of this README, there's a ready-to-use message you can copy and paste.
Eight jobs that happen reliably every day:
| Job | What It Solves |
|---|---|
| Start Each Day Focused | One command gives you three priorities. Heavy meeting day? Drops to two. Won't let you overcommit. |
| Never Miss a Commitment | Promises made in meetings extracted automatically. Three days old? Flagged. You can't forget. |
| Track Relationships | Before any call: what you discussed last time, open items, what they care about. Never walk in cold. |
| Accelerate Career Growth | Captures evidence automatically. Feedback from 1:1s, achievements, skills growth. Review-ready when you need it. |
| Manage Tasks Reliably | Work MCP syncs tasks with unique IDs across all files. Check off once, updates everywhere. Deduplication prevents doubles. Priority limits stop overcommit. Strategic alignment required. |
| Reflect & Improve | Captures mistakes → rules. Learns preferences. Each session makes the next better. |
| Keep Projects Moving | Auto-detects stalls (12+ days no update). Surfaces blockers. You know what needs attention. |
| Evolve Itself | System suggests improvements based on usage patterns. Monitors Claude Code releases daily - when new capabilities drop, explains what they mean for YOUR system and suggests implementations. Captures your improvement ideas too. AI ranks all by impact. /dex-improve plans implementation. System adapts to you. |
Want deeper context? See Dex_Jobs_to_Be_Done.md for the full framework.
Out of the box, working immediately:
/daily-plan, /meeting-prep, /career-coach, /week-review and more - invoke with /skill-name/dex-level-up suggests capabilities you haven't tried yet based on your usage patternsWeek 1: Use the scaffolded system. Value is immediate - commitments don't slip, meetings have context, day starts focused. System teaches you as you go.
Week 2: Start extending. Tell Claude what you need, it builds it. Not coding - just describing. Add integrations, customize workflows, adapt to your exact role.
Month 1: You're thinking like a builder. Understanding capabilities, spotting opportunities to automate, designing systems. AI fluency - the kind that compounds.
Why this matters: Time saved → invested in learning → deeper fluency → more sophisticated builds → greater impact → career advantage. The gap is widening now. People building these systems in Q1 2026 will have a year's advantage by summer.
Total investment: 30 minutes to set up. Two weeks to competence. The fluency compounds weekly.
Ideas die between having them and recording them. Deciding where things belong kills momentum.
Dex handles this through natural conversation. Just tell Claude things naturally:
You: "Sarah seemed worried about timeline but interested in Q2 pilot"
Claude: "I see you have 'Sarah's team onboarding' and 'Q2 Planning'
in your Week Priorities. Should I add this to Sarah's person page
and the Q2 Planning project?"
You: "Yes"
That's it. No special commands. No files to organize.
Strategic intelligence:
One decision instead of many. Immediate filing.
Great work happens daily, but evidence disappears. Review time becomes a scramble to remember what you accomplished.
Run /career-setup once (job description, career ladder, recent review, growth goals). From that point forward, Dex automatically captures career evidence:
| When | What Gets Captured |
|---|---|
| Daily reviews | Achievements worth saving for promotion discussions |
| Manager 1:1s (via Granola) | Feedback and development context |
| Project completions | Impact and skills demonstrated |
| Weekly reviews | Work tagged with career skills |
Run /career-coach anytime for:
| Mode | What It Does |
|---|---|
| Weekly Report | Generate professional update for your manager in 30 seconds |
| Monthly Reflection | Spot patterns — what's working, where to focus |
| Self-Review | Build annual review from accumulated evidence |
| Promotion Assessment | Gap analysis with specific development plan |
The coach adapts to your career level. Evidence compounds. The longer you use it, the more powerful it becomes.
Your data stays on your laptop. It's yours.
Tasks in multiple places (meeting notes, project files, person pages) don't sync in traditional systems. Check off one, others stay open.
Dex handles this with the Work MCP server - a Python-based automation layer that syncs tasks with unique IDs across your entire vault. When you process a meeting, action items get IDs like ^task-20260128-001. Tasks appear in both the meeting note and 03-Tasks/Tasks.md with the same ID.
Just tell Dex what you finished in natural language:
The Work MCP finds the ID, updates everywhere automatically (Tasks.md, meeting notes, person pages, project pages), adds timestamp: ✅2026-01-28 14:35.
No manual syncing. No duplicates getting out of sync. One source of truth.
This is why Python installation is required - the Work MCP server is the automation engine that makes task sync reliable and automatic.
Everything connects — from strategic pillars down to today's work:
%%{init: {'theme': 'neutral'}}%%
flowchart TD
A[Strategic Pillars] --> B[Quarter Goals]
B --> C[Week Priorities]
C --> D[Daily Plan]
B -.-> E[Tasks.md]
A -.-> E
C -.-> E
E --> D
D --> F[Daily Review]
F -.Tomorrow.-> D
style A fill:#e1f5e1
style B fill:#ffe1e1
style C fill:#e1e1ff
style D fill:#fff5e1
Strategic Pillars (your focus areas) → Quarter Goals (3-5 outcomes over 3 months) → Week Priorities (Top 3 this week) → Daily Plan (today's work) → Tasks.md (backlog tagged to goals).
Work backwards from career impact: What would make you incredibly happy you accomplished three months from now? Quarterly goals become the north star connecting daily work to career-defining outcomes.
See Dex_System_Guide.md for details.
You're likely using 20% of the system's capabilities because you don't know what you don't know.
Run /dex-level-up for progressive disclosure based on your actual usage. The system tracks which features you've used (stored locally in System/usage_log.md). When you run the command, it:
Week 1: suggests daily review workflows. Week 3: suggests custom MCP integrations.
The system teaches you progressively. You learn what you need, when you need it.
Want to explore without adding your data? Want to show colleagues what's possible before they commit?
Run /dex-demo on for pre-populated sample content that demonstrates all 8 Jobs to Be Done:
What's included:
/triage to demonstrate cleanup workflowEverything happens in System/Demo/ - your real vault stays untouched. Run /dex-demo off to switch back. Reset demo content anytime with /dex-demo reset.
Useful for:
/career-coach, /dex-backlog, etc.)The system captures learnings and improves over time:
/daily-review - captures learnings to System/Session_Learnings//week-review) - turns learnings into system improvements/dex-whats-new - surfaces learnings and new capabilities you can useWhat gets captured:
Day 1: helpful but generic. Week 2: knows your preferences, catches common mistakes. Month 1: adapted to your specific work style.
Each session makes the next one better.
31 role configurations. The scaffolding changes completely based on your answer.
Core Functions: Product Manager, Sales, Marketing, Engineering, Design
Customer-Facing: Customer Success, Solutions Engineering
Operations: Product Operations, RevOps/BizOps, Data/Analytics
Support Functions: Finance, People (HR), Legal, IT Support
Leadership: Founder
C-Suite: CEO, CFO, COO, CMO, CRO, CTO, CPO, CIO, CISO, CHRO, CLO, CCO
Independent: Fractional CPO, Consultant, Coach
Investment: Venture Capital / Private Equity
| Item | Cost |
|---|---|
| Cursor Pro | $20/month (Claude included) |
| Cursor Free | $0 (limited usage, enough to try it) |
| Time | 10 minutes to set up |
| Coding skills | None required |
Comprehensive guides included in the repo:
Start with what you need. Go deeper if you're curious. No forced learning paths.
These guides live in your vault after setup.
Get updates with one command - no technical knowledge needed.
Dex checks for updates every 7 days during /daily-plan:
🎁 Dex v1.3.0 is available. Run /dex-update to see what's new and update.
/dex-update
That's it. Dex shows you what's new, you confirm, and then it handles everything:
Time: 2-5 minutes
Technical knowledge: None
Risk: Zero - your data is always safe
/dex-rollback
Instantly restores the previous version.
Updates never touch:
For detailed instructions: See Updating_Dex.md
Dex works with Claude by default, but you can also use cheaper cloud models or offline local models.
Why configure alternatives?
Configure your options:
/ai-setup
What this offers:
Check your configuration:
/ai-status
For detailed guide: See AI_Model_Options.md
Dex works great with Obsidian for visual graph navigation.
Why Obsidian?
Enable Obsidian mode:
/dex-obsidian-setup
What this does:
Time: 1-2 minutes even for large vaults
Safe: Creates git backup before any changes
New to Obsidian? Watch this beginner's guide (5 min).
Obsidian is completely optional - Dex works perfectly in Cursor/terminal alone. Some users love the graph visualization for navigating their knowledge, others prefer the speed of terminal/Cursor. Both are first-class experiences.
Learn more: See Obsidian_Guide.md
Found this useful? Share with colleagues:
I've been using an AI operating system for the past few weeks that completely changed how I think about AI tools. It's not just another chat interface — it's a personal chief of staff that manages my day-to-day work (meeting prep, task sync, relationship tracking, strategic planning).
Here's what surprised me: the system teaches you AI fluency as you use it. You start with pre-built workflows, but within two weeks you're extending it yourself — not coding, just describing what you need and watching it build. It's basically a hands-on course disguised as a productivity tool.
If you're thinking about where AI is going and how to build organizational muscle around it, this is the best learning environment I've found. Real stakes, real work, immediate feedback. Non-engineers set it up in 10 minutes.
Check out Episode 8 of The Vibe PM Podcast for the full walkthrough, or dive straight into the GitHub repo. Would love to hear what you build with it.
Built with Claude. Created by Dave Killeen, Field CPO for EMEA at Pendo and host of The Vibe PM Podcast.
Thanks to Noah Brier for the Claudesidian repository that inspired me to bring AI into my markdown files with Obsidian last year and pulled me into this rewarding rabbit hole, and to Aman Khan from Arize for opening my eyes to the power of MCP servers for task management, and more broadly, for making PKM systems more deterministic and less wishy-washy.
Made an improvement to your Dex setup? Fixed something that was bugging you? Built a skill that others could use? Dave would love to see it.
You don't need to be a developer. Just tell Claude "I want to share my changes with the Dex community" and it'll walk you through the process. See CONTRIBUTING.md for the full guide.
PolyForm Noncommercial 1.0.0.
Commercial use is not allowed without a separate written commercial license from Dave Killeen. See LICENSE and COMMERCIAL_LICENSE.md for details.
Ready to start? Follow the setup instructions above — install Cursor, get the code, run /setup inside Cursor's chat panel.
💻 A curated list of papers and resources for multi-modal Graphical User Interface (GUI) agents.
An AI-powered custom node for ComfyUI designed to enhance workflow automation and provide intelligent assistance
Deterministic multi-agent pipeline for end-to-end software development, orchestrating CLI-based AI tools (e.g. Gemini, C
Native macOS app to monitor Claude AI usage limits and watch your coding sessions live