/context-sync

The aha: Before: After a client meeting, the campaign.md sat untouched for weeks. When Miller asked Claude about Pier West's strategy shift, Claude didn't know about the LP-only pivot discussed last Tuesday -- it was still referencing the old lead form approach. Now Miller runs /context-sync rennie pier-west after meetings and Claude catches up in 2 minutes. The next person who opens Cowork for that project gets answers that actually match what was decided.

What you need to know (2 min read)

/context-sync updates your client's context files by scanning five sources at once -- Slack, Gmail, Fireflies transcripts, ClickUp, and Drive -- then showing you what it found and asking you to confirm before writing anything.

Think of it as a research assistant that reads everything about a client across our tools, drafts the updates to the context files, and lets you approve or reject each change. It never deletes existing content. If something looks stale, it flags it for your review instead of removing it.

This matters because context files are what make Claude useful on your accounts. When they're out of date, Claude gives generic answers. When they're current, Claude knows why lead forms were turned off, who the day-to-day contact is, and what strategy the client approved last week. /context-sync is the fastest way to keep them current without manually editing markdown files.

How it works

When you run /context-sync, Claude does the following:

1. Figures out what you want

If you give it a client and project (/context-sync marcon hue), it jumps straight in. If you just type /context-sync, it asks which client and project you mean -- with a multiple-choice list so you don't have to remember exact names.

2. Runs 5 parallel scanners

Claude dispatches five scans at the same time, each looking at a different source:

Each scanner has a 45-second timeout. If one source is slow or inaccessible, the others still complete -- you get partial results rather than nothing.

3. Asks clarifying questions

Not everything the scanners find is clear-cut. Claude sorts findings into three buckets:

• High confidence (found in 2+ sources, or matches what's already in the file) -- written directly, no question asked
• Medium confidence (one source, clear context) -- Claude proposes an answer and asks you to confirm
• Low confidence (missing or contradictory info) -- Claude asks you an open-ended question

You'll get at most about 8 questions, one at a time, usually multiple choice. If Claude can't resolve something within that limit, it marks the section with a "needs review" note so you can fill it in later.

4. Shows a preview before writing

Before any file is changed, Claude shows you exactly what will be written:

• New files: You see the full proposed content
• Existing files: You see only the changed sections, diff-style (what's being added or modified)

You can approve, reject, or edit per file. Nothing gets written without your sign-off.

5. Writes the files

Claude updates the context files directly on the shared Drive. The files it can create or edit:

It never touches the ## Current Flags section in health.md (that's owned by the campaign monitoring agents) and never touches performance.md.

If something in the existing file looks outdated, Claude doesn't delete it -- it adds a stale flag (<!-- STALE? -->) and lists it in the summary so you can decide.

Try it yourself

1. Open Cowork
2. Type: /context-sync marcon hue
3. Claude scans all 5 sources (takes about 30-60 seconds)
4. You'll see something like:

Scanning Marcon / Hue...
Slack: 14 relevant messages found
Gmail: 3 threads found
Fireflies: 2 transcripts found
ClickUp: 8 active tasks
Drive: media plan, brief, 2 decks found

I have a few questions before updating:

1. The Fireflies transcript from Apr 8 mentions switching to
"awareness-only for Phase 2." Is that confirmed?
a) Yes, Phase 2 is awareness-only
b) No, that's still being discussed
c) Something else (tell me)

1. Answer the questions, review the preview, approve the writes
2. Claude confirms what was updated:

Done. Updated 3 files:
- Marcon/Hue/CLAUDE.md — added Phase 2 status, updated platform notes
- Marcon/Hue/campaign.md — added awareness campaign structure,
updated targeting section
- Marcon/Hue/health.md — added Known Context: "Phase 1 lead
campaigns paused intentionally for Phase 2 transition"

1 stale item flagged in campaign.md (old audience list from Nov 2025).
Sources scanned: Slack (14), Gmail (3), Fireflies (2), ClickUp (8), Drive (4).

Quick reference

When to run it

• After a client meeting where decisions were made. Strategy shifts, budget changes, campaign pauses -- run it so the context files reflect what was actually discussed.
• When a new project kicks off. /context-sync "new project for Wesgroup called Riverwalk" creates the full file set from scratch using whatever's already in Slack, Gmail, ClickUp, and Drive.
• When you notice context files are out of date. If Claude gives you an answer that's clearly wrong about a client, the context files probably need updating. Run /context-sync to catch up.
• Monthly as a hygiene check. Even if nothing major happened, running it once a month catches small drift -- new contacts, shifted timelines, updated account IDs.
• Before handing off an account. If someone else is covering your client (vacation, reorg), run /context-sync first so the context files are fresh for whoever picks it up.

Tips

• Client-only mode works too. /context-sync marcon (without a project) updates the client-level files only -- CLAUDE.md and contacts.md. Useful when you just need to update the team roster or add a new project to the list.
• You don't need to know markdown. Claude writes the files. You just answer questions and approve. If you want to make a manual edit afterward, the files are plain text with headings -- same as any notes doc.
• Pair it with /campaign-status. After running /context-sync to update the strategy and context, run /campaign-status to see how the live campaigns are performing against that updated context. The two skills complement each other.
• Don't stress about getting it perfect. Context files are living documents. Running /context-sync twice is fine -- it merges new information with what's already there. Each run makes the files more complete.
• If a scanner times out, re-run. Occasionally one of the 5 scanners hits a timeout (usually Fireflies on clients with lots of meetings). The other 4 still complete. If you need the missing source, just run it again.
• Hilda's trick: Run it the morning of a client call. The context files get refreshed, and then /pre-call-briefing has better material to work with.

Related

• Context Files Explained -- What context files are and why they matter
• How Claude Reads Your Client Folder -- How Claude uses the shared Drive folder structure