Introduction to Claude Cowork: teaching notes
Side-by-side notes for 03-praxis-introduction-to-claude-cowork.html (16 slides). The deck is what the room looks at; this is what you say, where you stop, and how you make each idea land for the person in front of you. Cowork is the delegation surface: you hand Claude an outcome, it plans, acts across your files and tools, and brings back a finished deliverable. It is the desktop sibling of everything /plato builds in Claude Code. Written from the deck and 03-introduction-to-claude-cowork-lessons.txt, against the Praxis teaching library. Method: teaching-notes-method.md.
How to use these notes
- Blocks marked Back to your card, Brief it like a new hire and Run it live are the three moves from T0, how we teach Praxis. Use the names and tasks on the group's Use Case Cards wherever you see [name].
- These are guidance, not a script. Teach the person, not the slides.
- Each teaching slide has a Pause, then ask block. Put the question, then stop. Do not fill the silence. If they freeze, one line: "Take your time, type anything when you're ready, including 'I don't know'." Then wait again.
- By background gives you a line per archetype (from
tutor/scenarios.md). Reach for the one that matches whoever is in the room and ignore the rest. They are a palette, not a checklist to read out. - Hold the voice (
train-the-trainer.mdPart 4): no "great question", no emoji, one term only: Claude Code. Underclaim. Cost is "about twenty dollars a month" and stop. - This course is the most hands-on of the set: every lesson ends in a "try it now" with their real files. Set the 80/20 ceiling before the first delegation, not after, or the first draft disappoints (
patterns.md: the 80/20 expectation). - Run the intake five questions first (
train-the-trainer.md) so you know which background you're teaching to, and what one task they'd delegate, before slide 1.
Stop chatting. Start delegating.
Set the frame: thirteen ideas, one per screen, and the shift that runs through all of them is from asking to delegating. You hand Cowork an outcome, not a question, and it brings back the finished thing.
"Thirteen ideas, one screen each. The whole course turns on one move: you stop typing questions and start handing over work. Chat is where you think out loud. Cowork is where you give Claude a job and it goes and does it, in your files, your apps, your browser. I'll show you, then I'll stop and ask where it fits your week."
The task they named in intake: name the one piece of work that eats their week, and promise that by the end they'll have handed exactly that to Cowork. That is the hook for the whole session.
The whole course on one screen
Four moves: meet Cowork, make it yours, run it everywhere you work, then share what works and keep it safe. Show the shape so nobody feels lost later.
"Here's the whole thing on one screen. We meet Cowork and hand it a first task. We make it yours so it stops needing re-explaining. We run it in your browser and your Office apps. Then we share what works across the team, safely. If you lose the thread, this is the map back."
Don't teach the spine, just orient. Twenty seconds, then move.
Chat thinks with you. Cowork does the work.
Same intelligence, three shapes on the desktop: Chat (think with Claude), Cowork (delegate to Claude), Code (build software). The shift that matters is Cowork: you hand it an outcome and it plans, executes, and delivers the whole arc, not a single answer.
"Three shapes of the same Claude. Chat is turn-by-turn, where you go to think out loud and draft. Cowork is different in kind, not degree: you describe a finished thing and Claude gathers the context, does the steps, uses your tools, and saves the deliverable back. Code is for developers building software. The instinct from chatbots is one question, one answer, then you stitch the rest together yourself. Cowork takes the whole stitch off your plate." (The deck's caption: Chat is to think out loud, Cowork is for the work you'd normally do yourself.)
- "What's a piece of work where the value was in the doing, not the thinking, that you assembled by hand across several tools?"
- "What does it mean to you to hand over the whole job, not just ask a question about it?"
(wait)
- Investigator
- stop asking about a subject; hand over "build the background report from this file".
- Analyst
- stop defining terms in chat; hand over "build the vendor comparison across every response".
- Designer
- stop brainstorming one concept; hand over "produce the full asset manifest for this campaign".
- Knowledge worker
- stop asking about one invoice; hand over "process the whole folder into a clean CSV".
- Reporter
- stop summarising one update; hand over "consolidate every update into Monday's briefing".
- Content
- stop drafting one line; hand over "draft the post against the back catalogue".
- Form-filler
- stop categorising one receipt; hand over "allocate the whole filing period to the template".
- Outreach
- stop writing one email; hand over "one proposal per customer in the folder".
- Exec
- stop pressure-testing one number; hand over "turn these inputs into a one-page board brief".
"Why not just use Claude in the browser?" surfaces here, the moment delegation clicks. Answer straight: the browser forgets between sessions and chokes on a folder of files; Cowork remembers, runs the steps, and saves a real deliverable back. (objections.md: browser / why not ChatGPT.)
Point it at a folder. That folder is the boundary.
Three setup choices: the working folder Claude reads and writes (the boundary for everything it touches), the connectors that reach your apps, and how closely it asks before acting. The folder is the single most important choice.
"You install the desktop app, sign in, pick Cowork, then make one decision that matters more than any other: which folder. That folder is the boundary, the room Claude works in. Pick the smallest one that holds the task, not your whole Documents drive. Connectors reach into your email, Drive and the rest, often read-only. And you choose how it asks: ask-before-acting is the default, and it always asks before deleting, no exceptions." (The deck's caption: cloud connectors are often read-only; your local folder is where Claude builds and iterates.)
- "For the task you named, which single folder holds everything it needs, and nothing it doesn't?"
- "What's in your wider drive you'd never want an autonomous tool wandering into?"
(wait)
- Investigator
- the one matter folder, not the whole case archive.
- Analyst
- the quarter's submissions folder, not every review you've ever run.
- Designer
- this campaign's briefs and brand tokens, not the studio's entire asset library.
- Knowledge worker
- this month's inbox of invoices, not all of accounts.
- Reporter
- this week's updates folder, not the team's whole shared drive.
- Content
- the post drafts and back catalogue, not the entire CMS export.
- Form-filler
- this filing period's receipts plus the template, nothing else.
- Outreach
- the customers folder and the knowledge base, not the full CRM dump.
- Exec
- the board-prep inputs folder, not the company-wide finance share.
On the map: the shared folder. A new starter gets one folder with what they need in it. You don't hand them the whole drive on day one.
- What's the one folder for your card? What's in it that shouldn't be?
The data-safety gate for almost everyone. Name the floor and the ceiling: Claude sees only what you can see, connectors are often read-only, and the folder bounds the rest. For banks and firms this is the IT/compliance discovery conversation, and the floor is Claude on the web with no install. (objections.md: IT/compliance/privacy; permission/auto.)
Three shapes of work worth handing off
Three patterns tell you what to delegate: multi-step, file-based, multi-tool. Plus when and where the handoff happens, /schedule for a cadence and Dispatch from your phone, both of which only run while your computer is on.
"How do you know a task is right for Cowork? Three patterns. It takes several steps, gather, compare, research, draft, format. It lives in real files and ends in a real file. Or it spans the tools you already use. Hit one or more and it's a handoff. And you don't have to be at your desk: you can schedule it to run weekly, or dispatch it from your phone, as long as your machine is on and Claude is running." (The deck's caption: the through-line is work you used to juggle in your head, handed off as a single task.)
- "What's a task you do that hits two or three of those at once, several steps, real files, several tools?"
- "Is there a piece of that you do on a cadence, weekly or monthly, that you'd happily never start by hand again?"
(wait)
- Investigator
- multi-step background research, drafted into the report, every claim cited.
- Analyst
- file-based, the vendor comparison across every submission in the folder.
- Designer
- multi-step, brief to asset manifest to CSV, in one pass.
- Knowledge worker
- file-based and recurring, the monthly invoice folder into a CSV.
- Reporter
- multi-tool and scheduled, Slack and Drive into Monday's briefing, every week.
- Content
- file-based, a draft built against the back-catalogue folder.
- Form-filler
- file-based and recurring, each filing period's receipts to the template.
- Outreach
- multi-tool, the CRM and customer folder into one proposal each.
- Exec
- multi-tool and scheduled, a Friday roll-up across email, Slack and the inputs folder.
"Is this for one-off projects or repeatable ones?" Both: ad-hoc gets faster because there's no UI to fight, repeatable gets cheaper because you can schedule it. Be honest about Dispatch's plan gate (research preview, Pro and Max) rather than overselling it. (objections.md: one-off / repeatable.)
Brief it like a smart colleague
A good Cowork prompt names three things: the deliverable, the inputs, and the nuance Claude can't guess. Then it asks clarifying questions, you answer, you steer mid-task if it drifts, and you review the result like a colleague's draft. More of the back-and-forth happens up front.
"Brief it the way you'd brief a capable colleague who's about to disappear into a task and come back with it done. Three things: name the deliverable, a one-page brief, a slide, a ranked list; name the inputs, which folder, which channel, which date range; and name the nuance only you would know. It'll ask a question or two to close the gaps, then go. If it drifts, jump in, the cost of a redirect is low. Then you review the file, not the chat." (framings.md: treat Claude like a junior on their first day; spell it out, the mistake is being too economical with words.)
- "Take that task. Brief me on it out loud, like I'm your new hire: the deliverable, the inputs, the one piece of nuance I couldn't guess."
- "What's the judgement in your job that you'd have to spell out, because a newcomer wouldn't know it?"
(wait, let them under-specify; the missing nuance is the lesson.)
- Investigator
- "deliverable: a background report; inputs: this matter folder; nuance: cite every source, never infer, never leave Evidence Gaps empty."
- Analyst
- "deliverable: a like-for-like comparison table; inputs: the submissions folder; nuance: mark blanks 'no data', name the basis when they differ."
- Designer
- "deliverable: an asset manifest plus CSV; inputs: these briefs and brand tokens; nuance: flag missing specs as 'ask client'."
- Knowledge worker
- "deliverable: a CSV; inputs: this invoice folder; nuance: leave absent fields blank, keep credit notes negative."
- Reporter
- "deliverable: Monday's briefing, five sections; inputs: the updates folder and the team Slack; nuance: cite who said what."
- Content
- "deliverable: a post in house voice; inputs: the back catalogue; nuance: reference one past piece, no rhetorical questions."
- Form-filler
- "deliverable: the filled template; inputs: this period's receipts; nuance: one section per receipt, drop nothing, totals must reconcile."
- Outreach
- "deliverable: one proposal per customer; inputs: the customers folder and knowledge base; nuance: only numbers from the file."
- Exec
- "deliverable: a one-page brief; inputs: the board-prep folder; nuance: facts not editorial, every decision has an owner and a date."
- [name], read out your card. Now brief Cowork on it out loud: the deliverable, the inputs and the one bit of nuance nobody could guess.
- Group, you're the new hire. Ask what you'd need to know before you start.
- Kick off
- Paste the brief from the room into Cowork, pointed at a test folder.
- Expect
- A few minutes, and it usually asks clarifying questions first.
- While it runs
- Answer its questions with the group. Read the plan out before you approve it.
- When it lands
- Review it like a colleague's draft. Name one thing you'd steer next time.
They'll write one vague line and be disappointed by the result. That's the teachable moment. Show the difference the nuance makes, then set the ceiling before the live run: "You'll get ninety percent of the way; the last ten you finish by hand. Even eighty is an eighty-percent cut in the work." (patterns.md: the 80/20 expectation.) The other half of the moment is review: the deliverable is the file, check it met the objective and that nothing is made up. (objections.md: hallucinate / make stuff up.)
Four ways Cowork gets better at your work
Four building blocks, each a different kind of knowledge Claude carries forward: global instructions (who you are), projects (one stream of work), skills (how a process is done), plugins (your role's expertise). Independent, and they compound. You don't start with all four.
"Right now you re-explain yourself every time. These four stop that. Global instructions: who you are and how you work, set once. Projects: one stream of work, so Claude acts like it's already on the team. Skills: how a specific process should be done, your way. Plugins: your whole role's expertise, bundled. The more it knows, the more it takes off your plate, and the context you supply once keeps paying off." (Previews framings.md: the folder is the memory; the context stops living in a chat you lose.)
- "What do you find yourself re-explaining to AI every single time you open it?"
- "If it just knew that, every time, what would you stop repeating?"
(wait)
- Investigator
- a skill, the house report rules and the never-infer standard.
- Analyst
- a skill, the fixed column set and the "no data" rule.
- Designer
- global instructions for brand basics, then a project per campaign.
- Knowledge worker
- a skill, the CSV schema and the leave-blanks-blank rule.
- Reporter
- a project for the weekly briefing, where last week's context carries forward.
- Content
- a project holding the house-voice guide and the back catalogue.
- Form-filler
- a skill, the template sections and category definitions.
- Outreach
- a plugin, the proposal format plus the CRM connector, shared with the team.
- Exec
- global instructions for your shorthand, then a project per board cycle.
Don't sell all four at once. Default is global instructions first, a project as recurring work surfaces, a skill when you're tired of re-explaining, a plugin once you have something worth sharing. The next two slides unpack standing context and skills, so plant the order and move.
Standing context: about you, and about the work
Two layers. Global instructions cover you, in every session (chat, scheduled, Dispatch). A project covers one stream of work, and quietly builds its own memory from your conversations inside it, so the next task opens with last week's decisions already in hand.
"Two kinds of standing context. Global instructions are a brief about you, set once in Settings: who you are, your shorthand, how you like output. They apply to every session. A project is scoped to one stream of work, a client, a recurring report, a launch, and it holds instructions, the folders it works from, and scheduled runs. The difference projects make is the last part: memory. Inside a project, every conversation adds to what Claude knows. Outside one, each session starts fresh." (framings.md: context window; here the project is the memory, not a chat that forgets the beginning.)
- "What's a stream of work, a client, a monthly report, a project, where every session would be better if it remembered the last one?"
- "What's the standing fact about you and your role that you'd want it to never forget?"
(wait)
- Investigator
- a project per matter, carrying the screening checklist and prior findings.
- Analyst
- a project per vendor review cycle, remembering last quarter's basis decisions.
- Designer
- a project per campaign, holding brand tokens and approved masters.
- Knowledge worker
- a project for the monthly close, remembering each supplier's quirks.
- Reporter
- a project for the weekly briefing, carrying the roster and last week's open items.
- Content
- a project for the blog, remembering the house voice and what's been published.
- Form-filler
- a project per filing period, remembering category edge cases.
- Outreach
- a project per segment, remembering each customer's situation and last contact.
- Exec
- a project for the board cycle, carrying KPI definitions and standing decisions.
On the map: global instructions are what you'd tell any new starter about how you work. A Project is the handover notes for one client or one report.
- For your card, what goes in your global instructions and what belongs only in its Project?
"Does it forget like ChatGPT does?" A bare chat does; a project doesn't, it builds memory as you go. This is the cleanest place to plant why standing context beats re-uploading files into a browser tab. (objections.md: browser / why not ChatGPT.)
03-...-lessons.txt). The distinction trips people up, so it's worth slowing down- Chat memory builds itself: turn it on and Claude learns from your conversations automatically, across all of them.
- Cowork carries context mostly from what you set up: global instructions (every session) and projects. Inside a project Claude does build memory automatically from the conversations there, but it's scoped to that project, not global to you.
- Each task otherwise starts fresh apart from your global instructions; the project is what makes "the next task opens with last week's decisions in hand" true.
- Operational caveat (scheduled tasks): a scheduled task only runs when your computer is on and Claude is running. If the machine is closed, asleep, or off at the scheduled time, Claude picks it up as soon as you're back and tells you it was delayed. (Same is true of Dispatch.) Mental model: Chat = one self-building memory, global. Cowork = context you mostly author (global + project instructions + folders), plus project memory that's walled into the project.
A skill is a playbook Claude loads when the task matches
A skill is a folder of files that teaches Claude how to do one kind of work your way. Up to four parts, only the first required: SKILL.md (instructions), assets (templates, brand), references (examples of good output), scripts (the repeatable calculation). Claude loads it automatically when a task matches, and you build it just by talking.
"A skill is a playbook. A folder where you write down how one kind of work should be done, once, so Claude does it your way every time. The brief, SKILL.md, is the only required part: what it does, when, and how, written like a runbook for a new colleague. Add templates as assets, your best past work as references, and a script for the part that must come out identical every time. Claude loads it on its own when the task matches. And you build it by talking: 'I want a skill for the thing I keep re-explaining, walk me through what you need.'" (framings.md: skill file as institutional memory: the rules that lived in your best person's head, pulled out onto disk so a new joiner produces the same work.)
- "What's a process you do the same way every time, where the 'right way' lives in someone's head?"
- "If that person left tomorrow, what would walk out the door with them?"
(wait: this lands hard for regulated and professional rooms.)
- Investigator
- a background-report skill, the eight sections, cite-or-cut, Evidence Gaps never empty (the PI exemplar).
- Analyst
- a vendor-comparison skill, fixed columns, "no data" rule, a script for the table.
- Designer
- an asset-manifest skill that reads briefs and lists every variant with specs.
- Knowledge worker
- an invoice-to-CSV skill with a review queue for anything ambiguous.
- Reporter
- a weekly-briefing skill in the five-section format, citing each contributor.
- Content
- a house-voice skill, the past posts as references, the structure as the brief.
- Form-filler
- a receipt-allocation skill that drops nothing and reconciles totals via a script.
- Outreach
- a proposal skill, one per customer, five fixed sections.
- Exec
- an exec-brief skill, revenue, at-risk, decisions, steady, on one page.
- Is there a skill hidden in your card? What would the first three lines of SKILL.md say?
- [name], how is that different from what you'd put in the Project?
"I can't read code" arrives when they see a script in the skill folder. Answer straight: don't read the code, the intelligence is in the SKILL.md in plain English; the script just enforces the repeatable part the same way every time. (objections.md: can't read code.)
A plugin bundles skills around a job
Where a skill is one playbook, a plugin is several, plus the connectors and subagents they need. Two shapes: an end-to-end pipeline (steps in sequence, like a monthly close) or a function toolkit (the skills a team reaches for most). Anthropic publishes plugins for common roles; install, customise, or build your own.
"A plugin is a package built around a job. Two shapes. A pipeline: several skills that run in sequence, like pull the actuals, build the variance, draft the board memo. Or a toolkit: the skills a function reaches for most, bundled so a new teammate installs one thing and has the whole set. The point is the expertise travels with the install, not the person. Anthropic publishes them for finance, legal, sales, support; start with /setup-cowork and it finds the one that fits your work." (framings.md: skill file as institutional memory, scaled: a plugin is your team's way of working, installable.)
- "Is the work you'd hand over a single sequence of steps, or a set of separate jobs you do often?"
- "What would 'your role, installable' look like, the toolkit a new joiner in your seat would want on day one?"
(wait)
- Investigator
- a pipeline, screen, research, draft, gap-check, for a full matter.
- Analyst
- a toolkit, comparison, benchmarking, data-gap report, the recurring reviews.
- Designer
- a pipeline, brief to manifest to spec-check, per campaign.
- Knowledge worker
- a pipeline, extract, flag, reconcile, for the monthly close.
- Reporter
- a pipeline, gather, consolidate, format, for the weekly briefing.
- Content
- a toolkit, draft, voice-check, repurpose, the recurring content jobs.
- Form-filler
- a pipeline, read, allocate, reconcile, for each filing period.
- Outreach
- a pipeline, research, personalise, draft, per customer.
- Exec
- a pipeline, the monthly board cycle, synthesis to one-page brief.
Don't conflate plugin with the app "skills" from Claude 101 or the Praxis skill file. Keep the nesting clear: a plugin is several skills bundled with their connectors. If they don't yet have one skill, plugins are a later step, name it and move on.
Claude in Chrome: the bridge for tools with no connector
For dashboards, vendor portals and web apps behind a login, Claude reads and acts on the page itself, then hands the results back to Cowork. You stay signed in, it works in your authenticated session; one conversation, both surfaces.
"Some of your tools have no connector: the BI dashboard, the procurement portal, the CRM behind single sign-on. Claude in Chrome is the bridge. It reads and clicks the page in the session you're already signed into, pulls what you need, and hands it back to Cowork to build the deliverable. One conversation across both. The line that matters: it can't log in for you, you stay signed in, and it asks before sensitive actions." (The deck's caption: you stay signed in; Claude in Chrome may not be available on some enterprise plans.)
- "What lives in a browser tool you check regularly that has no clean export, a dashboard, a portal, an internal app?"
- "If Claude could pull from that page and build the summary, what would you stop copy-pasting?"
(wait)
- Investigator
- a public-records or court-listing portal behind a login.
- Analyst
- the BI dashboard where vendor metrics live.
- Designer
- a retailer's spec or listing portal with no API.
- Knowledge worker
- a supplier portal where invoices are downloaded one by one.
- Reporter
- an internal status dashboard the team updates by hand.
- Content
- the CMS analytics view behind the publishing login.
- Form-filler
- a tax or filing portal with no export.
- Outreach
- the CRM web app behind single sign-on.
- Exec
- the finance or KPI dashboard checked every Monday.
- Kick off
- Ask Claude in Chrome to read a figure from a dashboard or portal you're signed in to.
- Expect
- A minute or two.
- While it runs
- Narrate what it clicks and reads. Ask the group what they'd check.
- When it lands
- Check it read the right numbers from the right page.
Honesty on the plan gate (it may be off on some enterprise plans) and on authentication (Claude works in your signed-in session, it can't sign in for you). For regulated rooms, fold this into the IT discovery conversation rather than overselling it. (objections.md: IT/compliance.)
Claude for Microsoft 365: inside the document
Claude shows up as an add-in in Word, Excel, PowerPoint and Outlook, working on the file you have open. One conversation can carry context across the apps. The rule of thumb: Cowork when work pulls from many sources to a deliverable; M365 when you're editing the Office file in place.
"The same Claude turns up inside the Office apps as an add-in. In Excel it writes formulas and variance commentary and debugs your #REF errors. In PowerPoint it reads your slide master and builds native, editable charts. In Word it drafts and reformats in place with tracked changes. In Outlook it triages and drafts replies with the context of the thread. And one conversation carries the context across, the Excel model becomes the deck becomes the email. Reach for Cowork to build from many sources; reach for M365 when you're editing the file itself." (The deck's caption: the two hand off cleanly, and the file is the file in both.)
- "Which Office app do you spend the most hours in each week?"
- "What's the cross-app journey you do by hand, numbers in Excel, into a deck, into an email?"
(wait)
- Investigator
- Word for the report draft with tracked changes for review.
- Analyst
- Excel for the model and variance commentary cited back to cells.
- Designer
- PowerPoint to build slides that match the brand master.
- Knowledge worker
- Excel to clean and reconcile the extracted figures in place.
- Reporter
- Outlook to draft the briefing email, PowerPoint for the readout slide.
- Content
- Word to draft and reformat the post in house style.
- Form-filler
- Excel to lay the allocations into the template's structure.
- Outreach
- Word for the proposal, Outlook for the personalised covering email.
- Exec
- Excel to the board model, PowerPoint to the deck, Outlook to the invite, in one conversation.
People assume M365 and Cowork compete. They don't: Cowork builds the first draft from many sources, M365 is where you refine the Office file in place. Most real work uses both. If add-ins are IT-managed, that's a setup conversation with their admin.
The folder sets the boundary; the prompt sets the bounds
Cowork always asks before deleting, that's the floor. On top of it: set up safely (dedicated folder, back up the irreplaceable, test on copies), write prompts that leave no room for the wrong action (name destructive verbs, name the bounds, draft-only until trusted), and stay alert in the moment (read the plan, watch for drift, approve confirmations deliberately). Not the tool for audit-trail work.
"An autonomous tool with file and app access needs guardrails, and most of them are yours to bring. Three layers. Set up: a dedicated folder, not a catch-all; back up anything irreplaceable; test new tasks on copies. Write the prompt: name destructive verbs precisely, name the bounds, 'only Q3 files', keep it draft-only until you trust it. And in the moment: read the plan before it runs, watch for scope creep, and when a confirmation appears, read it. Most mistakes aren't a safeguard failing, they're someone clicking through a dialog that wasn't quite the action they meant." (The deck's caption: the dialog exists because the action matters, treat it that way.)
- "In the folder you'd point Claude at, is there anything irreplaceable that needs backing up first?"
- "What's a destructive word, 'clean up', 'archive', 'cut', that you'd want to spell out more precisely before handing it over?"
(wait)
- Investigator
- regulated, audit-trail work, Cowork isn't captured in compliance logs; prepare, you file.
- Analyst
- scope the prompt to "only this quarter's submissions", and draft-only first.
- Designer
- back up master files before any batch run; test on copies of assets.
- Knowledge worker
- name the bounds, "only this month's invoices, don't touch prior folders".
- Reporter
- keep scheduled briefings draft-only until you've watched a few run cleanly.
- Content
- "revise the draft, don't overwrite the published version".
- Form-filler
- back up the prior year's filing before re-running the allocation.
- Outreach
- draft-only, "don't message anyone", until you trust the per-customer output.
- Exec
- anything customer- or board-facing, Claude prepares, you ship.
On the map: what you'd let a new starter do unsupervised in their first week. Draft only until you trust them is how you'd treat a person too.
- For your card: which actions would you allow, which need your OK first and which never?
"What if it does something I didn't want?" lives here. Give the controls before the capability: ask-before-acting is the default, always-asks-before-deleting is the floor, and you check the end. The honest line: Cowork isn't the tool for anything you wouldn't hand a quick colleague to do unsupervised, or for regulated work that needs an audit trail. (objections.md: permission/auto.)
An eval is a try-out: with the skill, and without
Before a skill leaves your desk, see it side by side against the baseline (same prompt, no skill). No code, no test scripts, just your judgement. The bar isn't perfect evals, it's that the cases you care about pass meaningfully better than the baseline and you've named the ones you don't yet handle. Built into skill-creator; change one thing at a time.
"An eval is just a try-out. Don't let the word scare you. skill-creator runs the same realistic request two ways, once with your skill, once without, and shows you the pair. You read both and answer two questions: would I send the skill version, and if not, what's off? You say it in plain English, 'too formal', 'skipped the summary', and Claude revises. It's a loop, not a one-time gate. You ship when the cases you care about beat the baseline and you've named the edge cases you don't handle yet." (The deck's caption: change one thing at a time; the bar is meaningfully better than baseline, not perfect.)
- "If you handed your skill to a colleague, how would they phrase the request differently from you, and would it still hold up?"
- "What's the one edge case in your work, the awkward receipt, the contradictory source, that you'd want to test it on first?"
(wait)
- Investigator
- a thin file where the report must still surface Evidence Gaps honestly.
- Analyst
- two providers whose numbers can't be compared on the same basis.
- Designer
- a brief that's silent on a required spec, does it flag "ask client"?
- Knowledge worker
- a credit note and an OCR-noisy scan in the same batch.
- Reporter
- rough, half-pasted-Slack notes, does it still attribute and structure?
- Content
- a topic close to a past post, does the voice hold without copying?
- Form-filler
- a receipt that fits two sections, does it pick the more specific and footnote the other?
- Outreach
- a customer file missing a number, does it refuse to invent one?
- Exec
- a long input, does the brief still fit one page and lead with the decision?
- Kick off
- Run the same prompt twice, with the skill and without it.
- Expect
- A couple of minutes each.
- While it runs
- Ask the group to predict where the two will differ.
- When it lands
- Put them side by side and agree which cases the skill really handles better.
This slide is the human-premium moment made concrete: the eval is your judgement, and only you can spot what a novice would miss. Don't let "eval" read as ceremony. If the first pass looks great, you're done. (Ties to the 80/20 loop: the last ten percent is this judgement.)
From one laptop to the whole team
A skill that started as one person's way of working becomes something a teammate can install, through your org's private marketplace. An owner (team lead, IT, enablement) publishes it at one of four levels: Available, Installed by default, Required, Hidden. Keep it healthy: one named owner, evals before every publish, specific names, quarterly review.
"The payoff: what started on your laptop becomes something the whole team installs. Inside a company, that runs through a private marketplace an admin manages. You hand your plugin to whoever owns it, and they publish it at a level, available to opt into, installed by default, or required for things everyone must run the same way. Teammates see it in their Directory, labelled as coming from your company, and your updates flow to them automatically. Keep it alive with four habits: one named owner, evals before every publish, specific names, and a quarterly review to retire what nobody runs." (framings.md: skill file as institutional memory; this is the moment one person's know-how becomes the firm's.)
- "Of the skills you'd build, which two or three would your immediate team want most?"
- "Who in your organisation owns the tooling, the person you'd hand a plugin to?"
(wait: if they don't know the second answer, that's their real next step.)
- Investigator
- the background-report skill, so every analyst files to the same standard.
- Analyst
- the vendor-comparison skill, so every review uses the same columns and basis.
- Designer
- the asset-manifest skill, so every campaign lists variants the same way.
- Knowledge worker
- the invoice-to-CSV skill, so the whole AP team extracts identically.
- Reporter
- the briefing skill, so anyone can run Monday's update in your absence.
- Content
- the house-voice skill, so every writer's draft starts on-voice.
- Form-filler
- the allocation skill, so every filing reconciles the same way.
- Outreach
- the proposal plugin, so the whole BD team ships consistent, specific proposals.
- Exec
- the exec-brief skill, so the office produces the same one-page format every cycle.
Plan honesty: private marketplaces are an Enterprise feature and an admin switch someone has to flip. If it's not live, you can still export the plugin folder and hand it to a teammate directly, manual, but it works. Don't oversell a marketplace they can't switch on yet.
Hand off the work. Teach it your way. Trust, but review.
The whole course in three lines: Cowork goes beyond chat so you can delegate real work; make it yours with standing context, skills and plugins; run it across your browser and Office; then share what works and keep it safe. The throughline is delegation; everything else builds on it.
"If you keep one thing: hand off the work, don't just chat about it. Teach Cowork your way once, with global instructions, a project, a skill, and the next deliverable comes back better and faster. Trust it to do the doing, but review the result like a colleague's draft, because you own what goes out. Everything we saw today, the browser, the Office apps, the marketplace, is a way to do that in more places."
Their task from slide 1, and the next concrete step: "Next time we point Cowork at your real folder and hand it the one you named." Then the session-improvement habit: "at the end, tell it to look back at what we did badly today and save how we fixed it." (patterns.md: close every session by teaching the system to improve.) Point forward too: the durable, scriptable version of everything they liked lives in a folder in Claude Code, which is the next session and the heart of the Praxis method.
Verified against the Cowork lesson ("Review the finished deliverable"). The deliverable is the artifact, not the chat. So before you send it on or act on it, review it the way you'd review a colleague's work, with your discernment on. Most concretely: check the facts. If Claude cites figures, ask it which documents it pulled from, then verify those against the source yourself. The rule of thumb the course sets: Claude can prepare; you ship. Anything outward-facing (sending the doc, posting the announcement, pushing the change) is yours to approve, however much AI helped make it.