Michael Gardon · CHIEF AI Accelerator
Accelerator / Curriculum / 2.1 Conversation Continuity
Phase 2 · Collaborate

Continue your work across a new thread, without repeating yourself

Re-explaining your own work is the most expensive habit you have. This kills it.

What you'll walk out with
~6 min read · then ~15 min to build it
Callback

The problem

You already know a long thread atrophies. But your inclination is to pick up working in the same thread. Here's the habit that works.

The checkpoint works. It also depends on you remembering to do it, and doing it well, every single time. That's the part that breaks.

Need a refresh? → 1.6 Conversation Architecture

Part A · The doc
The frame

Make your Chief document status

Good project documentation means anyone can pick up the work tomorrow. Including someone who wasn't there.

The test of good project documentation: a stranger can pick up the work without asking you a single question.

When you work with AI

The one difference

The build

How to do this

The thread is where the work happens. It is not where the work lives.

The status doc

  • What's decided, what's open, what changed, what's next.
  • It's what they'd bring to a check-in.
  • Rewritten constantly. Stays under a page.
  • It replaces scrolling up.
Status is not a record of what happened. It's a picture of where you are right now, and what's next.

The template

Notice the first paragraph. The doc tells Chief what to do with it. That's not decoration. A doc that carries its own instructions works even before you build anything.

# STATUS — [project name]

**Claude, read this first, every session.** This is the source of truth for
where this work stands. Before we stop, rewrite this file so the next session
starts from an accurate picture. Overwrite the old content, do not append.
Update "Status now," "Done this session," and "Next actions." If anything in
"The basics" changed, fix it too. If I forget to ask, remind me: "Want me to
update the status doc before we stop?"

## The basics
- **What this is:** [one or two sentences: what we're doing, who it's for]
- **What done looks like:** [how we'll know it's finished]
- **Where the work lives:** [doc, folder, repo, tool — with the link]
- **Rules that don't move:** [format, voice, constraints, anything you
  keep having to repeat]

## Status now
[Plain language, a short paragraph. What works, what's half-built, what's
untouched. Written so a fresh session with zero memory understands exactly
where things stand.]

## Decisions made (don't re-litigate)
- [decision] — [why]
- [decision] — [why]

## Ruled out
- [option] — [why not]

## Open questions / waiting on
- [what's blocked, or a choice you still need to make]

## Done this session
- [what changed today, in plain language]

## Next actions
1. [the single most important next step, spelled out]
2. [then this]
3. [then this]

## How to use this doc
- **Starting:** open a new thread, paste this in, say "Read this and pick
  up where we left off."
- **Ending:** say "wrap." That one habit is what makes any thread resumable.
- **This doc holds context only.** It doesn't hold your work product. That
  lives wherever it lives.

**Last updated:** [date] — [what was happening at that moment]
SectionWhat it does for ChiefWhat it does for you
The basicsFrames every answer it givesNames which project this is
Status nowStops it solving a solved problemRebuilds your context in ten seconds
Decisions madeStops it reopening settled callsStops you re-deciding at 11pm
Ruled outStops it pitching the dead optionStops the hour-long re-litigation
Open questionsTells it what to push onTells you what's actually blocked
Next actionsGives it a starting instructionRemoves the "where was I" tax

Setup

Now you can start any thread from where you left off.

Pitfall: the status doc that lies

A status doc nobody updates is worse than none. You'll trust it.

What to do: That's why wrap exists. The habit is the system. The doc is just where it writes.

The progression

Keeping status current

Three ways to close the loop. They differ in how much of it your hands have to do.

1 · Beginner

Manual: you paste it back

The command: "Update the status doc before we stop."

  • That's the whole thing. Six words.
  • The doc's own header tells Chief what to do next. You just pull the trigger.
  • Chief rewrites it and hands you the text.
  • You paste it into your doc. Ten seconds.
Needs: nothing. No connector. No setup. Works today.
Costs: you paste it in at the start, you paste it out at the end.
The catch: it only happens if you remember. That's the whole risk.
2 · Intermediate

Versioned in your Chief Vault, through a connector

  • Connect Google Drive or OneDrive. Point Chief at your Chief Vault.
  • Now it reads the status doc itself. No paste-in.
  • At the end, it writes the update back as a new file, dated.

Tradeoffs

  • A connector doesn't edit your doc inline. It can't.
  • It can create new files. It cannot change one that already exists.
  • (Tested against Google Drive, July 2026. Same behavior on OneDrive.)
  • So every update lands as a new dated doc, sitting next to the old one.

Which means:

  • Accumulated backlog. You'll have a stack of STATUS – [project] – 2026-07-16 files. Not a problem, but you'll have to clear them out yourself at some point. Connectors can't delete.
  • Chief has to always read the most recent. You have to tell it, in thread, to pull the latest version. Until you build the skill. Then it's handled.
A stack of dated status docs isn't a mess. One undated doc you can't trust is.
Needs: a connector, pointed at your Chief Vault.
Costs: occasional cleanup.
You get back: both pastes. Gone.
3 · Pro

Automatic, via Cowork

  • Your Chief Vault isn't reached through an API here. It's a folder, on your machine.
  • Cowork works in that folder directly.
  • It reads the doc. It rewrites the doc. Same file.
  • No paste. No versions. No cleanup. No stack to sort through.
Every other rung ends with your hands. This is the one where the loop closes without you.
Needs: Cowork, with access to your Chief Vault folder. You can keep that folder in the cloud. Cowork works on a synced copy on your machine.
Costs: threads aren't reachable from the web or mobile right now. Chat vs. Cowork →
You gain: documentation done for you, on command. Chief creates, files and organizes all of it.
Reads your docUpdates your docYour hands
BeginnerYou paste it inHands you textPaste in, paste out
IntermediateItselfNew dated docCleanup, sometimes
ProItselfSame file, in placeNone

Start at Beginner today. You can climb whenever you want. The doc doesn't change.

The move

Turn the command into a skill

You keep typing the same instruction. Write it down once, and one word runs it.

Look at what you're actually doing:

That's a skill:

Why not just say "summarize this"?

Picture the status update from a project manager who doesn't get it.

"Today we discussed pricing. We talked through several models and considered the competitive landscape. We also touched on the launch timeline."

You now know nothing you didn't know this morning. What did we land on? What's still open? What do you need from me?

The good one writes four lines. "Pricing is $2,400, flat. Killed the tiers, too hard to explain. Launch date still open, waiting on legal. Need thirty minutes Thursday."

What you actually need is shorter, and different:

That last one is the one people lose. It's also the one you'll waste an hour re-litigating.

That's not a summary. It's a handoff. It's what you'd tell your chief of staff on the way out the door.

So here's the case for writing it down:

A skill is how you stop depending on your own discipline.

Part B · Build it
The build

Build wrap

Fifteen minutes. Then you never type the instruction again.

What you're about to have:

Where the instructions live is the only choice here. Same text every time. It maps to the three rungs above.

RungWhere wrap livesWhat wrap does with the doc
BeginnerYour Project's instructionsHands you the text. You paste it back.
IntermediateUploaded to your accountSaves a new dated doc in your Chief Vault.
ProA file in your Chief VaultRewrites the file in place.

The instructions

---
name: Wrap
description: Close out a work session and rewrite the status doc. Use when the user says wrap, close out, end session, or done for now.
---

# Wrap

Close out this work session so the next one starts where this one ended.

## Steps

1. Find the current Status. It was probably pasted in near the top of
   this thread. If it lives in a connected Chief Vault, find every file
   whose name starts with "STATUS" for this project and read only the
   MOST RECENT one. Ignore the older ones. If you can't find it, say so
   and ask.
2. Look back over this thread and pull out only what changed:
   - Decisions made. Not topics discussed. Decisions.
   - Things ruled out, and the reason why.
   - Questions still open.
   - The single next move.
3. Rewrite Status. Do not append. Rewrite it so it reads as
   "here is where we are now," not "here is what happened."
4. Keep it under one page. Cut anything that is settled and no longer
   shapes the next move.
5. Deliver it the way this setup allows:
   - No connector: output the whole rewritten Status in one block I can copy.
   - Connected Chief Vault: save it as a NEW file named
     "STATUS — [project] — [today's date]". Do not try to edit the old
     one, you can't. Do not delete the old one, you can't. Leave it.
   - Cowork: rewrite the Status file in place. Same file.

## Rules

- Decisions, not discussion. "We talked about pricing" is worthless.
  "Pricing is $2,400, flat, no tiers" is the whole point.
- If something was ruled out, say why. Future me will ask.
- If two things in this thread contradict each other, do not pick one.
  Flag both and ask.
- Never delete an open question just because nobody mentioned it again.

The line that solves the version stack

Look at Step 1. "Read only the MOST RECENT one. Ignore the older ones."

On Intermediate, that was your job. You had to remember, every session, to tell Chief which doc was real. Forget once and it briefs you off a stale doc without either of you noticing.

Now it's in the skill. You don't remember it. It does.

Step 5 does the same thing. It saves the new doc dated, and it knows not to try to edit or delete the old one, because it can't.

Every rule you were carrying is now in the file.

The other half: resume

---
name: Resume
description: Pick up work where the last session ended by reading the status doc. Use when the user says resume, pick up where we left off, where were we, or catch me up.
---

# Resume

Start this session from where the last one ended.

## Steps

1. Find the status doc for this project.
   - Pasted or attached in this thread? Use it.
   - In a connected Chief Vault? Search for files named
     "STATUS — [project]". There will be several, dated. Read ONLY the
     most recent. Ignore the rest.
   - A file in a Cowork folder? Read it.
   - Can't find one? Say so and stop. Do not guess.
2. Read all of it. The basics, status now, decisions, ruled out,
   open questions, next actions.
3. Tell me in under 100 words:
   - Where we are.
   - What's next. The top item from Next actions.
   - Anything in Open questions that's waiting on me.
4. Name the file you read and its date. If it's more than a week old,
   say so out loud.
5. Stop. Do not start work until I tell you what we're doing.

## Rules

- Never invent state. If the doc doesn't say it, you don't know it.
- Nothing under "Ruled out" gets reopened. That's settled.
- If the doc contradicts itself, flag it. Do not pick a side.
- Reading an old version poisons everything after it. If you're not
  certain which is most recent, ask.

Step 4 is the safety net

"Name the file you read and its date. If it's more than a week old, say so out loud."

This is the line that catches the failure you'd never catch yourself. Chief reads a stale doc, briefs you confidently off it, and you have no reason to doubt it. Making it say the date out loud turns an invisible failure into an obvious one.

Two skills, not one:

Two words now hold the thing you used to hold in your head.

Where to put them

Beginner: paste them into a Project
Least setup, if you already have a Project.
  • Open your Project → Instructions → paste both blocks above. Done.
  • You get: wrap and resume fire in any thread inside that Project.
  • It costs: they only live in that Project.
  • Build a second Project? Paste them again.
  • Change the wording? Change it in both.
  • They don't travel.

Use this if you already work in a Project and want the habit running in five minutes. Upgrading later is a copy and a paste. The text is identical.

Don't have a Project? You don't need one. Use Intermediate.

Intermediate: upload them as real skills
The default. Fifteen minutes once. Then they're everywhere, forever.
  • Uploaded skills live in your account, not in a Project.
  • Every thread. Every Project. Every device.
  • You trained the habit once. It doesn't leave when you change desks.
  • Works on Free, Pro, Max, Team, and Enterprise. (Checked July 2026.)
Step 00 · Check this first
  • Settings → Capabilities → turn on code execution.
  • Skills don't run without it. This is where people get stuck.
  • Thirty seconds now saves a confusing ten minutes later.
Step 01 · Download both
  • Hit ↓ Download wrap.zip and ↓ Download resume.zip above.
  • Both are already packaged. Folder, SKILL.md, correct structure.
  • No folder to build. Nothing to zip.
Step 02 · Upload them
  • Go to Customize → Skills.
  • Upload both ZIPs. Toggle both on.
Step 03 · Test them before you trust them
  • Open a new chat. Paste in a status doc. Type resume. Then type wrap.
  • Watch what each one does.
  • Nothing fired? It's one of two things. Code execution is off (Step 00), or the description doesn't include the word you typed.
  • Fix the description. Re-upload.
Step 04 · Use them for real
  • Next work session, type wrap at the end.
  • Do it once and you'll feel the difference on the way back in.

Want to change one first? Download the raw SKILL.md, edit it, then paste it into a new chat and say: "Package this as a ZIP I can upload in Customize > Skills. One folder called wrap at the root, with SKILL.md inside." Worth doing once, just to see that Chief can package its own skills. That's the whole trick behind Phase 3.

You just built a skill. That's the whole mechanism. Phase 3 is this, with bigger instructions.
Pro: keep them in your Chief Vault
For when your files and your Chief are in the same place.
  • In Cowork or Claude Code, a skill is a file in your folder.
  • It sits next to the work it's about.

You get:

  • No paste-back. It rewrites your status doc on disk. You never touch it.
  • You edit the skill like any file.
  • It's version-controlled. See what it looked like in March. Roll back a change that made it worse.
  • It lives next to your status doc and your work. Not in a settings menu.

It costs:

  • You need a folder Chief can reach.
  • You need to be comfortable with files.
  • Different surface, different tradeoffs.

Use this if you already work out of a real folder. If that sentence meant nothing to you, use Intermediate. You lose nothing. Same file. It moves when you're ready.

Which surface to use when is its own thing. Chat vs. Cowork →

The rhythm

What good looks like

Two minutes at the end buys you a warm start every time.

01
  • Open a new thread. Type resume. It finds the doc, reads the current one, tells you where you are.
02
  • Do one job. Just the one.
03
  • Watch for the signs. You know these from 1.6. Don't push through them.
04
  • Type wrap. Skim what it wrote. Fix what it got wrong. Ten seconds, and it matters more than the whole thread.
05
  • Close it. Nothing was in there.

Two words. Everything between them is the actual work.

Four things to carry out

  • The thread is where work happens, not where it lives.
  • Status is the doc. resume opens it, wrap closes it.
  • Decisions, not discussion. A summary of what you talked about is worth nothing.
  • A skill is a standing instruction. You just built two. That's the rest of the program.
Watch for these

Pitfalls

The status doc that grows.

  • Six weeks in it's four pages. You've stopped reading it.
  • Now you're pasting four pages of stale context into every thread.

What to do: Status is where you are, not how you got here. If it's settled and it doesn't shape the next move, cut it. Over a page? Cut.

Wrapping only when the thread is dying.

  • You wrap when you feel the wall coming.
  • So you only ever capture the messy end.

What to do: Wrap when the job is done, not when the thread is done. Different moments.

Trusting the wrap.

  • It guessed. Usually well.
  • Sometimes it records a decision you never made. Now that's your source of truth.

What to do: Read it. Ten seconds. You'd read a status update before acting on it. Read this one.

Forgetting to paste it back.

  • You wrapped. You read it. You closed the thread. You never saved it.

What to do: The wrap isn't done until the doc changed. This is the one step Pro deletes.

The thread that keeps going anyway.

  • You have the system. You're still in a four-day thread. It's right there, and it's warm.

What to do: Having the system doesn't remove the pull. 1.6 told you the signs. Wrap and close.

What's next

2.2 · Projects & Context

Back to the program map →