How a Personal OS
Compounds Over Time

Setup vs. Compounding: What Changes

The biggest shift is moving from telling Claude what to do to Claude already knowing what to do. Here's what that looks like:

Memory in Cowork

You want Claude to remember how you work without re-explaining it every session. In Cowork, two things carry that memory:

• Your CLAUDE.md — the instructions and rules you write at the root of your folder. Claude reads it at the start of every session. When you correct Claude, say "add that as a rule to my CLAUDE.md."
• A learnings file — ask Claude to keep 99_System/learnings.md, a running list of preferences and corrections it should honor. Point Claude at it when you start something new.

The Workflow Library

The first guide kept it to a couple of saved shortcuts. A mature Personal OS leans on many more — each one a few lines of instructions Claude reuses, so you stop re-explaining a workflow. In Cowork these live as plain prompt files in 99_System/Prompts/: write the steps down once, then ask Claude to run one by name. The auto-firing /slash-command version, where each becomes a real installed skill, is the Claude Code build.

What I Actually Run

Here's how mine cluster, by job:

How a Workflow File Looks

A prompt file is just instructions — a title and the steps. The same file works as a Claude Code skill if you add a frontmatter header; in Cowork you can skip it. Here's the call workflow:

---
name: call
description: Create or update a call note in 20_Areas/Calls/.
  Auto-populates People and Companies directories.
allowed-tools: Glob(*), Read(*), Write(*), Edit(*)
---

# /call

Create a structured call note.

## What to do

1. Ask for contact name and date (default today).
2. Check if the person exists in 20_Areas/People/. If yes, read their
   profile for context. If no, create from the template.
3. Check the contact's company in 20_Areas/Companies/. If exists,
   update Engagement Timeline; if not, create from template.
4. Create the call note in 20_Areas/Calls/YYYY-MM-DD_Contact-Name.md
   using the call schema in CLAUDE.md.
5. When the source is a Granola meeting, always read the full transcript
   via get_meeting_transcript. Never rely on the AI-generated summary.
6. Surface any prior notes with this contact from past calls.

Build the Core Five

Past the daily agenda, these do the most work in a typical week: meeting capture, pre-meeting prep, a learnings habit, Monday kickoff, and Friday wrap-up. Paste the prompt below and Claude keeps them as prompt files in 99_System/Prompts/, so you can ask for any of them by name.

Please set up five workflows for me. Keep each as a prompt file in 99_System/Prompts/ so I can ask for it by name.

1. A "call" skill:

---
name: call
description: Create or update a structured call note in 20_Areas/Calls/. Auto-populates People and Companies entries.
allowed-tools: Glob(*), Read(*), Write(*), Edit(*)
---

# /call

Create a structured call note.

## What to do

1. Ask for the contact name and date (default today).
2. Check 20_Areas/People/ for the contact. If found, read their profile for context. If not, create one from the template.
3. Check 20_Areas/Companies/ for their company. If exists, update Engagement Timeline. If not, create from template.
4. Create the call note at 20_Areas/Calls/YYYY-MM-DD_Contact-Name.md.
5. When the source is a Granola meeting, ALWAYS read the full transcript via get_meeting_transcript. Never work from the AI-generated summary; summaries drop and distort decisions.
6. Surface any prior notes with this contact.
7. Append a Relationship History line to the person's profile.


2. A "brief" skill:

---
name: brief
description: Generate a one-page pre-meeting brief for a person, company, or topic. Pulls vault context for a structured briefing.
allowed-tools: Glob(*), Read(*), Write(*)
---

# /brief

Generate a one-page brief.

## What to do

1. Ask what or who the brief is about.
2. Search 20_Areas/People/, 20_Areas/Companies/, and 20_Areas/Calls/ for relevant context.
3. Synthesize into a brief with: who/what, relationship history, open items, recommended angles for the meeting.
4. Save to 00_Inbox/YYYY-MM-DD_Brief_Topic.md and tell me where it is.


3. A "remember" skill:

---
name: remember
description: Review the current session and save durable learnings to my vault.
---

# remember

Review what happened in the session and propose what to save.

## What to do

1. Scan the conversation for: corrections I gave, durable facts I shared, non-obvious choices that worked, patterns worth keeping.
2. For each candidate, propose a one-line entry.
3. Ask which to save; append the approved ones to 99_System/learnings.md, and add any lasting rules to my CLAUDE.md.


4. A "weekstart" skill:

---
name: weekstart
description: Monday kickoff. Daily agenda, overdue triage, project health, people follow-ups, weekly focus.
allowed-tools: Bash(*), Read(*), Write(*)
---

# /weekstart

Monday morning routine.

## What to do

1. Run the same scan as /today to build today's agenda.
2. Scan 10_Projects/ for projects with no activity in 7+ days. Flag them.
3. Scan 20_Areas/People/ for entries where last_contact is more than 14 days ago and follow_up is true.
4. Ask me for a one-line focus for the week.
5. Save everything as 00_Inbox/YYYY-MM-DD_Weekstart.md.


5. A "weekend" skill:

---
name: weekend
description: Friday wrap-up. Weekly review, unresolved items, next week preview.
allowed-tools: Bash(*), Read(*), Write(*)
---

# /weekend

Friday wrap-up.

## What to do

1. Read this week's daily agenda files in 00_Inbox/.
2. Summarize what moved, what stalled, and what got committed to.
3. Pull open action items into a single list.
4. Propose 3 priorities for next week.
5. Save as 00_Inbox/YYYY-MM-DD_Weekend.md.


Create all five now and confirm when done.

Capture Pipelines: The Input Layer

The first guide treated the vault as a place you write into. The leverage move is to make it a place that fills itself from your real meetings. By the time you sit down to ask Claude "what did I learn this week?", the raw material is already there.

The lowest-effort starting point is meeting transcripts, and the easiest path is Granola.

Granola for Meeting Capture

Granola sits on top of Zoom, Google Meet, and Microsoft Teams and captures transcripts plus AI-generated summaries for every call. It ships with a built-in Claude connector, so once you connect it, Claude can pull recent meetings on demand without you copying anything.

Two parts to set up:

Please set up a Granola filing workflow for me.

Keep it as a prompt file in 99_System/Prompts/ and run it by name:

---
name: granola
description: Pull recent Granola meeting transcripts and file them into 20_Areas/Calls/ as structured call notes. Skip routine internal meetings and solo notes.
allowed-tools: Read(*), Write(*), Edit(*), Glob(*)
---

# /granola

File recent Granola meetings into the vault as call notes.

## What to do

1. Use the Granola connector to list meetings since the last run (default: past 7 days).
2. For each meeting, decide whether to file or skip:
   - SKIP: solo notes, recurring 1:1s with my manager, routine internal ops syncs, social events, held meetings with no transcript
   - FILE: external calls, partner meetings, customer calls, new contacts, strategic discussions
3. For each meeting to file:
   - Pull the FULL transcript via get_meeting_transcript (never the AI summary; it drops and distorts decisions)
   - Check 20_Areas/People/ for the participants; create or update profiles
   - Check 20_Areas/Companies/ for their org; update Engagement Timeline
   - Create a call note at 20_Areas/Calls/YYYY-MM-DD_Meeting-Name.md
4. Report a summary: filed N, skipped M, and why each was skipped.

Confirm when the skill is installed.

The Voice System

Without a voice system, Claude writes in Generic Professional. With one, Claude writes in your voice — with your cadence, your word choices, your structure preferences, even your banned phrases. This is the difference between Claude as a draft generator and Claude as a ghostwriter who actually sounds like you.

Where Voice Lives

My voice system sits in 99_System/Context_Library/ as a small set of files:

99_System/Context_Library/
│
├── speaking_positions.md     # My actual positions on the topics I'm known for
├── quotable_moments.md       # Lines that landed on stage or in writing
├── email_voice_guide.md      # How I actually write emails (tone, structure)
├── audience_delight_profile.md # What I'm like as a speaker
└── slide_playbook.md         # Visual and verbal patterns for decks

The Files That Carry the Most Weight

Build Your Voice Files

The most accurate source of your voice is your own sent mail. The prompt below tells Claude to use an email connector (Outlook, Gmail, or whatever you have wired up) to read your actual sent emails and produce the voice files from real evidence.

I want you to build my voice system in 99_System/Context_Library/.

First: confirm you have access to an email connector (Outlook, Gmail, Microsoft 365, or similar). If no email connector is enabled in this Claude environment, tell me which one I should set up and walk me through enabling it. Do not proceed until email access is working.

Once you have email access:

1. Read 30 to 50 of my actual sent emails from the past 6 months. Prioritize emails I wrote from scratch over forwards or one-line replies. Include a mix of audiences: internal team, peers, external partners, vendors, and any leadership.

2. Analyze the patterns. Look for:
   - Voice and tone characteristics
   - Sentence and paragraph rhythm
   - Vocabulary I favor and vocabulary I avoid
   - Punctuation habits (em-dashes, parentheses, exclamation marks)
   - Salutations and closings I actually use
   - How my tone shifts across audiences

3. Create these four files in 99_System/Context_Library/:

   - email_voice_guide.md: how I write emails. Tone, structure, salutations, closings, banned phrases. Include 2-3 short before/after examples showing how generic professional writing would get rewritten in my voice.

   - speaking_positions.md: start with section headers for the topics that show up most in my outgoing mail (Strategy, Industry POV, Team Philosophy, etc.). Leave each section mostly empty with a one-line note that it will be filled in over time from calls and webinars.

   - quotable_moments.md: start blank with a brief explanation of what belongs here (lines that landed, on stage or in writing).

   - audience_delight_profile.md: start with what you can infer from my emails about how I show up with different audiences. Flag that this file will get richer once speaking transcripts are added.

4. Report back: how many emails you analyzed, what patterns stood out, and the four files you created.

Companies as Wiki Entries

This is an architectural decision the first guide didn't cover. In my vault, every external organization that touches my work gets a Company file in 20_Areas/Companies/. That file is the canonical wiki entry for the org — the place that consolidates partnership context, products, history, and strategic fit. People files are individual profiles that link into the Company file.

Why This Pattern

People come and go. Companies persist. When someone changes employers, I update the company: field on their People file — their relationship history stays intact, but the wiki entry stays attached to the org. When someone new joins an existing partner, I just add a row to that Company's Key People table and they inherit all the context.

What a Company File Looks Like

---
type: company
name: [Org Name]
website: [domain]
relationship: [strategic-partner | partner | vendor | press | other]
first_contact: YYYY-MM-DD
last_contact: YYYY-MM-DD
---

# [Org Name]

## What They Do
[One paragraph. Plain description.]

## Relationship Snapshot
[Why this org matters to my work right now.]

## Key People
| Name | Role | Contact | Note |
|------|------|---------|------|
| [[Person-Name]] | [Role] | [email] | [one line] |

## Internal Counterparts
[Who on my side owns this relationship.]

## Products / Workstreams
[Concrete things in play.]

## Engagement Timeline
| Date | Touchpoint | Call Note |
|------|------------|-----------|
| 2026-05-20 | Intro call | [[2026-05-20_Org-Name]] |

## Strategic Fit
[How this org sits relative to competitors and our strategy.]

## Open Items
- [ ] [item] — @owner — due YYYY-MM-DD

## Related
[Wikilinks to projects, parallel companies, reference memories.]

The Compounding Rule

Three cross-references happen automatically at creation time, enforced by my CLAUDE.md:

• New person at an existing company → update that Company's Key People table in the same edit.
• New company that already has People profiles → backfill the company: field on every existing person who works there.
• New Call note involving an external org → link to the Company in the call's Related section, and add the row to the Company's Engagement Timeline.

Install the Templates

The prompt below installs the three templates (People, Companies, Calls) and adds the filing conventions to your root CLAUDE.md so Claude enforces the cross-reference rules automatically.

I want to install the relationship-tracking pattern in my vault. Please:

1. Create 20_Areas/People/_template_person.md with this frontmatter:

---
type: person
name:
company: "[[Company-Name]]"
role:
relationship: # client | colleague | partner | vendor
first_contact:
last_contact:
follow_up: false
tags: []
---

## Context
<!-- Role, how we met, what they care about -->

## Relationship History
<!-- Key interactions, auto-appended from calls -->

## Personal Details
<!-- Family, interests, preferences -->

## Open Items
<!-- Commitments made, questions to follow up on -->


2. Create 20_Areas/Companies/_template_company.md with this frontmatter and sections:

---
type: company
name:
website:
industry:
relationship: # strategic-partner | partner | vendor | press | other
first_contact:
last_contact:
tags: []
---

## What They Do
[One paragraph.]

## Relationship Snapshot
[Why this org matters to my work right now.]

## Key People
| Name | Role | Contact | Note |
|------|------|---------|------|

## Internal Counterparts
[Who on my side owns this relationship.]

## Products / Workstreams
## Engagement Timeline
| Date | Touchpoint | Call Note |
|------|------------|-----------|

## Strategic Fit
## Open Items
## Related


3. Create 20_Areas/Calls/_template_call.md with:

---
type: call
contact: "[[Person-Name]]"
company: "[[Company-Name]]"
date:
tags: []
---

## Context
## Discussion
## Decisions
## Action Items
## Follow-up


4. Add a "Filing Conventions" section to my root CLAUDE.md that explains:
   - Companies are wiki entries; the canonical hub for an org.
   - People link to their company via the company: frontmatter field.
   - Calls link to both.
   - When a new person is added at an existing company, also update that Company's Key People table.
   - When a new company is added and People profiles already exist for that org, backfill the company: field on those People files.
   - When a new call note is created, also update the Company's Engagement Timeline and append a line to the person's Relationship History.

Create all three templates and the CLAUDE.md addition now.

Shipping From the Vault

The vault doubles as a workshop where I produce branded artifacts and deploy them to the web.

What I Ship From Here

Why Shipping Belongs in the Vault

Two reasons:

• Source material is already here. The transcript I want to turn into a webinar page is in 20_Areas/Keynotes/. The brand logo files are in 30_Resources/. The voice that should narrate the page is in 99_System/Context_Library/. Building elsewhere means dragging all that context to a new tool.
• Workflows can compose. A workflow like add-webinar uses the voice system to draft the page copy, the brand resources for visuals, and the deploy infrastructure to ship. Each piece was built for a different reason; the workflow stitches them together. The deploy-grade ones — pushing code, uploading video — run their smoothest in the Claude Code build.

Build Your Own Shipping Skill

Shipping skills are the most personal part of a Personal OS — they depend on what you publish, your brand, and your deploy infrastructure. The prompt below works for any recurring publishing workflow you've done manually two or three times.

I have a recurring publishing workflow I want to turn into a skill. Walk me through the build.

Ask me these questions one at a time:

1. What's the artifact I'm shipping? (one-pager, slide deck, webinar page, social post, branded PDF, etc.)
2. Where does the source material live? (vault folder, Drive, transcript service, etc.)
3. What does the artifact need from my voice or brand system? (writing voice, logos, colors, templates)
4. Where does it get published? (Vercel, GitHub Pages, S3, LinkedIn, Drive, intranet, etc.)
5. What manual steps do I currently do, in order?

Once I've answered all five:

1. Propose a skill name and short description.
2. Draft a SKILL.md that orchestrates the full workflow: pulling sources, applying voice and brand, producing the artifact, deploying or filing it, confirming success.
3. Flag any external setup I need (API keys, account access, MCP connectors).
4. Keep it as a prompt file in 99_System/Prompts/ and tell me how to trigger it.

Connectors: What to Wire In

Connectors let Claude reach beyond your folder — into project management tools, calendars, CRMs, your inbox, cloud storage. In Cowork you turn them on under Settings → Connectors. After months of use, only a few are load-bearing.

What I Actually Use

Writing Rules & Guardrails

Beyond the voice system (which teaches Claude how you write), guardrails are rules that prevent Claude from producing content you'd have to heavily edit or that could embarrass you. These live in your CLAUDE.md or in feedback memories.

Communication Guardrails

If you work in an industry where AI hype language is common, write a rule that pulls drafts back to specifics:

## Communication Guardrails

When drafting communications, presentations, or talking points
for internal audiences, keep AI framing practical and grounded.
Focus on specific tools and wins. Flag if a draft leans too heavy
on sweeping transformation language.

Internal vs. External Content

Claude can easily mix internal language (project codenames, partner pricing details, internal tool nicknames) into content meant for external audiences. The fix is a one-line rule:

## Content Creation

When creating content for external audiences (partners, clients,
press, industry contacts), always ask "Is this internal or external?"
if it's unclear. Never include partner pricing, financial figures,
internal program names, or compliance-sensitive language in external
deliverables.

Data Honesty

If Claude is helping you with reports, analytics, or research, this rule prevents quiet fabrication:

## Data & Reports

Never fabricate or extrapolate data. If I provide three months
of data, do NOT create year-over-year comparisons. Verify
relationships, geography, numbers, and frameworks before writing
them into scripts or briefings. When source data is insufficient,
flag it instead of filling the gap.

Hard-Won Lessons

These come from months of daily use. Each one represents a problem that took time to diagnose.

The Weekly Rhythm

A mature system benefits from a weekly maintenance pass. About 15 minutes. Most of it runs through saved workflows.

The Vault After Six Months

Here's what mine looks like now. Items in green are additions beyond the foundation setup. They all emerged from real workflows.

Personal_OS/
│
├── 00_Inbox/                          # Daily agendas, transcripts, captures
│
├── 10_Projects/                       # Active work, each with its own CLAUDE.md
│
├── 20_Areas/
│   ├── Calls/                         # Meeting notes (per call)
│   ├── Companies/                     # Wiki entry per external org (NEW)
│   ├── People/                        # Individual profiles, linked to Companies
│   ├── Keynotes/                      # Speaking engagement archive (NEW)
│   ├── Events/                        # Conference session notes (audience-side) (NEW)
│   ├── Market_Research/               # Ongoing research area (NEW)
│   └── Press_Coverage/                # Media mentions log (NEW)
│
├── 30_Resources/
│   ├── Research/AI/                   # Sources, Digests, Stats_Library (NEW)
│   ├── Research/Tourism/              # Same structure, different domain (NEW)
│   ├── Webinar_Transcripts/           # With TOPIC_INDEX for voice retrieval (NEW)
│   ├── Brand_Resources/               # Logos, colors, fonts, usage rules (NEW)
│   └── AI_Generated_Images/           # Reusable image library (NEW)
│
├── 40_Archives/
│
├── 50_Personal/                       # Personal projects, kept separate
│
├── 99_System/
│   ├── Context_Library/
│   │   ├── speaking_positions.md      # Voice system (NEW)
│   │   ├── quotable_moments.md        # Voice system (NEW)
│   │   ├── email_voice_guide.md       # Voice system (NEW)
│   │   ├── slide_playbook.md          # Deck design system (NEW)
│   │   └── recurring_meetings/        # Standing roster files (NEW)
│   ├── Profiles/
│   ├── Scripts/                       # Automation scripts and cron jobs (NEW)
│   └── claude_code_config.md
│
├── Apps/                              # Software projects deployed from here (NEW)
│
└── CLAUDE.md

The structure isn't the system — the structure is the residue of the system. Folders appear because workflows need a home. Skills appear because patterns repeat. Memories appear because lessons stick. None of it was planned upfront. All of it was built one piece at a time.