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The Sidekick field guideStart reading

A beginner-to-intermediate guide

Working
with AI.

From your first useful task to repeatable workflows and automation

Learn to give AI a useful job, improve the result, and build a routine you can reuse. Start wherever you need help:

Try your first task About ten minutes · No setup required
01Try one task in ten minuteswith a complete example you can paste into ordinary chat.02Find an answerwhen feedback gets forgotten, files get confusing, or you want to delegate more.03See what you could makewith examples of research, content, and project work.

The guide covers Claude Cowork, Microsoft Copilot Cowork, and ChatGPT Work. Read one part now and return when the next job needs it.

Product guidance checked September 12, 2026. Availability varies by app and account. Working habits are Sidekick recommendations; examples are fictional.

Part 01 / Chapters 1–3

Start with one useful task

Give AI a job. Keep your judgment.

After this part, you can brief a small task, check the answer, and improve it.

The clear unfurl
Chapter 01

Your first useful task

Set aside about ten minutes for this practice. The aim is to produce something useful and improve it once. Learning twelve new product names is optional.

Give it a small, complete job

Open the AI app your organization permits. Paste the following request into a new chat or work task. Everything needed is inside the prompt.

This is a fictional practice task. Label the output PRACTICE.

Turn these meeting notes into:
1. Decisions made.
2. Actions, with an owner and a date only when the notes provide them.
3. Open questions.
4. A short follow-up draft for my review.

Use only these notes. Do not turn a suggestion into an agreement.
Mark missing information as unknown. Do not send anything or change files.

Notes:
We discussed a customer workshop. The team chose an online format.
Sam will check facilitator availability by 18 September 2026.
Jo suggested a budget of $2,000, but nobody approved it.
We still need to decide who will invite customers and when the workshop runs.

Compare the result with this example

An acceptable answer could look like this. The wording can differ; the facts should not.

PRACTICE

Decision: Run the workshop online.

Action: Sam will check facilitator availability by 18 September 2026.

Open questions: Is the proposed $2,000 budget approved? Who will invite customers? What is the workshop date?

Follow-up draft: We agreed to run the workshop online. Sam will check facilitator availability by 18 September. We still need to confirm the budget, invitation owner, and workshop date.

If the AI says the budget is approved, the answer is wrong even if the layout is lovely. A polished table can still contain nonsense. It has simply put on a tie.

Make one meaningful correction

Suppose the draft is accurate, but the open questions are buried at the bottom. Try:

Put the unresolved decisions first so I can see what needs attention.
Then show the agreed decision and Sam's action.
Keep the budget clearly marked as a proposal, not an approval.
Do not change the facts or send anything.

Check that the revised answer changed the order without changing the meaning. You have now practised briefing, checking, and steering. Those three habits support much larger work.

Leave yourself a useful return point

Give me a five-line handoff I can save and use next time:
the task, what we finished, unresolved questions, the useful writing preference,
and the next step. Keep it labelled PRACTICE. Do not save it into real client records.

Save that note somewhere you can find it. In a new chat, attach or paste it and ask, “What is the next step?” A sound answer should recover the open decisions. It should not claim the workshop happened.

You can stop here. Try this with one small piece of approved work next. Leave confidential or sensitive material out until your organization has approved the tool and data use. If you want to understand why the exercise worked, continue below.

Chapter 02

What changes when chat becomes work?

Think of a chat as a conversation at a colleague's desk. You ask a question, discuss options, or improve a paragraph together. In a work task, you give that colleague a result to produce and the resources they need to produce it.

“What belongs in a workshop proposal?” starts a discussion. “Use these notes and our approved template to create a workshop proposal, flag missing terms, and return a draft” delegates a job.

The difference is the amount of work you hand over. Ordinary chat can also use tools, read files, or produce documents. Work modes are designed to carry a larger task through several steps while you steer and review. OpenAI's Chat and Work comparison explains this distinction for ChatGPT.

What the AI actually does

A typical work task moves through a loop: read the request, plan the next step, use an available tool, inspect what happened, then continue or ask for help. The model supplies language and reasoning. Tools let it search, calculate, read files, or make changes. An agent is an AI system arranged to carry out work through such steps.

The colleague analogy has a limit. AI does not carry human accountability or reliably know when it is wrong. It can misunderstand a source, miss a condition, or sound certain about a guess. Your brief and checks still matter.

Choose the mode that fits the job

What you need A sensible starting point
Explain a term, discuss an idea, rewrite a sentence Chat
Compare several files and create a report Work or Cowork
Complete a substantial task with a clear finish line A work task, with a goal where supported
Run a proven update again next Monday A scheduled workflow after testing

Start with the simplest mode that can finish the job. A two-line reply does not need its own operations department.

Three products with similar ambitions

Claude Cowork is Anthropic's way to delegate work across files and connected tools. Microsoft Copilot Cowork operates in Microsoft's environment, including supported Microsoft 365 services. ChatGPT Work is OpenAI's work experience for producing reviewable results using available files and tools. They are separate products. A skill or button in one is not automatically present in another. See the platform notes for the right starting route.

Try it: take a question you often ask AI and rewrite it as a deliverable. Replace “Help with our report” with “Produce the report from these sources, with these checks.”

See what you could make

These are small illustrative outputs, using invented inputs. They show the shape of useful work. They are not product recommendations or reports of actual results.

A comparison that helps you choose. Suppose you need four seats and data export. Your sample research notes say Option A supports both for $40 per month; Option B has six seats for $30 per month but no export. A useful result makes the deciding fact visible:

Illustrative research resultMake the deciding fact visible.
Decision note / Practice
Which option fits?

Required: four seats and data export.

Option A$40 / month

Four seats supported
Data export included

Meets both requirements
Option B$30 / month

Six seats
No data export

Fails the export requirement

Decision: Option A meets both requirements. Option B costs less but fails the export requirement.

Requirements drive the recommendation. Before buying, verify these details against the current product pages. These options and prices are invented.

The value is an explicit comparison against your needs. For real research, supply or retrieve current sources and inspect the claims that determine the choice. Give it a useful brief.

One source, ready for different readers. A fictional approved notice says: “The community repair event is Saturday, 10 a.m. to noon. Volunteer registration closes Thursday.” Ask for a newsletter item and a short social post:

Newsletter: Help out at Saturday's repair event, from 10 a.m. to noon. Register as a volunteer by Thursday.

Social draft: Have two hours on Saturday? Volunteer at the repair event, 10 a.m. to noon. Register by Thursday.

The AI changes the format while keeping the facts. You check the tone and add the approved registration link. It should not invent a venue, guarantee repairs, or publish the drafts. Check and improve the work.

A project update that surfaces the next decision. Instead of rereading two weeks of notes, you get an update that says:

Illustrative weekly update / Project ASame facts. A more useful first line.

Review changes what the reader sees first. It does not change what happened.

Project A / Week 2 / PracticeFirst draft
Weekly update
Progress
The invitation is approved. A room is available, and the team lead chose next Thursday for the 10-person pilot. Thursday replaces the earlier Tuesday proposal. [B1, B2, B3]
Decisions needed
Assign who will send invitations and when. Neither is specified. [B4]

Review note: Put the unresolved decision first so the team lead can act on it.

Project A / Week 2 / PracticeAfter review
Weekly update
Decisions needed
Assign who will send invitations and when. Neither is specified. [B4]
Progress
The invitation is approved. A room is available, and the team lead chose next Thursday for the 10-person pilot. Thursday replaces the earlier Tuesday proposal. [B1, B2, B3]

What improved: The next decision is visible first. The facts and source labels are unchanged.

This is an excerpt from the fictional complete walkthrough. The invitation is approved and Thursday is confirmed. Invitation delivery still needs an owner and a send date.

You can see what needs your attention. The complete walkthrough supplies both weeks' notes, the prompts, the checks, and the path to repeating the work.

Choose a job you understand well enough to judge. Familiar work gives you a better error detector than an impressive-looking answer does.

Chapter 03

Give the AI a brief it can act on

A useful brief tells the AI what a capable colleague would need to know. You do not need to guess a secret prompt formula.

Explain the outcome, the reader, the sources, the constraints, and how you will judge the result. Include the details that change the work. An entire company archive is usually a poor substitute for the current template and the right notes.

For the workshop, “Make a proposal” leaves the AI to guess what is being offered, to whom, and on what terms. This is more useful:

Create a review draft of a one-page workshop proposal for a prospective customer.

Use the attached meeting notes and the approved proposal template.
The reader needs to decide whether to discuss scope with us.
Use plain language and make the proposed outcome easy to find.

Treat the online format as agreed. The budget, date, and invitation owner
are still unresolved. Mark them clearly; do not invent terms.

Done means: the draft follows the template, its factual claims match the notes,
unresolved terms are visible, and the next decision is clear.
Return the draft for review. Do not send or publish it.

Ask me only for missing information that would materially change the result.

If you cannot yet describe the result, say:

Help me define this job before building it. Ask one question at a time about
the outcome, audience, source material, and what a good result must contain.
Then show me a short brief we can use.
Illustrative proposal excerptA draft that shows what is still undecided.
Workshop / PracticeReview draft
Customer
workshop

Discussion draft from the practice notes.

FormatOnline Agreed
Budget$2,000 Proposed only
DateTo be confirmed
InvitationsOwner unresolved

Next decisionConfirm the missing terms before finalizing the proposal.

01Keep agreed facts clear.

The notes support an online format.

02A suggestion stays a suggestion.

The budget is visible without becoming an agreed price.

03The next decision is easy to find.

Missing terms become useful questions.

Tell it what matters most

Sometimes requirements compete. A proposal cannot explain every detail and remain a short introduction. State the tradeoff: “Prioritize a clear buying decision. Put technical detail in an appendix.”

Give a good example when you have one, and explain what to copy from it. “Use the structure of this proposal” should not become “reuse its old client's price and promises.”

Voice works too. Talk through the job, then ask the AI to write back the brief. Check names, numbers, and dates after dictation. You can be conversational without leaving the assignment vague.

Ready to move on: the AI can restate the desired result and its important limits in a few sentences. If it cannot, fix the brief before asking for more output.

Part 02 / Chapters 4–6

Build continuity

Leave a thread you can pick up.

After this part, you can organize sources, save a handoff, and reuse useful feedback.

Jade courtyard
Chapter 04

Projects, folders, files, and context

These words describe different parts of your working setup. Treat a project as the room for an area of work, a folder as a place to keep files, and a chat or task as one job being discussed in that room. A room can contain several jobs. A folder does not know which document is correct merely because its name sounds official.

Context is the information the AI has available for the current work: your request, selected conversation history, instructions, files it has read, and results returned by tools. “The file is somewhere in the project” and “the AI used that file” are different statements.

Picture your working setupA room. A cabinet. A working desk.

Related does not mean loaded. Choose what belongs on the desk for this task.

An analogy, not an app layout
  1. 1
    Project

    The room for an area of work. Several tasks can happen here.

  2. 2
    Folder

    The cabinet that stores files. Its name does not make a file current.

  3. 3
    Source files

    The notes and documents you choose for this job.

  4. 4
    Context

    What the AI has available now: your request, loaded guidance, files and tool results.

A file in the cabinet is not automatically open on the desk. Ask which sources the AI actually used.

Start with a small working set

For recurring workshop work, a useful arrangement might be:

Workshop work/
  Brief and current state.md
  Sources/
    Approved template.docx
    Meeting notes.txt
  Drafts/
    Workshop proposal v1.docx

This is an example, not a required folder system. If your company already has a sensible place for these files, use it. A .md file is plain text with simple formatting. You can keep the same information in an approved document if that fits your tools better.

Keep one agreed current version. Rename old drafts clearly. “Final”, “Final revised”, and “Final actually final” is a naming system with a short life expectancy.

Use a new task for a distinct outcome, such as preparing the proposal versus checking the final presentation. Continue the same task for revisions to the same result. Keep related work in the same project when its sources and permissions belong together.

A project is not always a folder

In ChatGPT, a cloud project can hold chats, uploaded files, instructions, and connected sources. Local desktop projects can attach folders on your computer. A cloud project does not by itself give access to your local drive. See OpenAI's projects guide.

Claude Cowork Projects can gather folders, instructions, links, and project memory. Claude's chat projects and Cowork projects have distinct behaviour; check the current Cowork Projects guide before moving work between them.

For Microsoft Copilot Cowork, use the files and task views available in your account. Its input and output areas help you find source files and generated work. Do not expect Claude's local folder setup to be the Microsoft setup. Microsoft's getting-started guide shows its file flow.

Context has limits

Picture a desk with limited working space. The filing cabinet may contain years of material, but only some of it is open on the desk. Long conversations can be summarized; tools may retrieve only part of a source. A new task may need to read saved notes before it can continue accurately.

For important work, ask: “Which exact sources did you use, and what could you not access?” If two sources conflict, ask the AI to show the disagreement. Tell it which source has authority rather than allowing it to quietly combine incompatible versions.

Separate client work when information must remain separate. Use your organization's access controls as well as clear project boundaries. A folder title or a prompt saying “only use this client” is not a security lock. Connected accounts can have their own access scope, as explained in the ChatGPT Work overview.

Try it: give the AI the current template and one old example. Ask it which source governs structure and which governs facts. Correct any confusion before it drafts.

Chapter 05

Start, steer, and finish a session

A session routine is a small handover habit. It helps avoid spending the first ten minutes reconstructing the last ten minutes of yesterday.

“Start my session” and “Wrap up” are useful names for that habit. They are not universal commands that install a memory system. They work when your instructions explain them and the AI can reach the saved record. Otherwise, use the full prompts below.

Start with the current state

Start my session. Read the attached current-work note and the sources it names
that you can access. Tell me the last completed step, unresolved decisions,
and the next useful action. Distinguish saved facts from your assumptions.
Tell me if a source is missing. Do not change files or send anything yet.

Once oriented, give the next job. You need not ask for a new plan after every small step. If the result is heading off course, steer it while it works: “Keep the agreed outline. Focus this revision on the budget section.”

Finish with a useful handoff

Wrap up this task. Summarize the completed work, decisions, unresolved questions,
exact output location, and next action. Include only reusable corrections
that matter to future work.

If updating our current-work note is already authorized, update it and show me
what changed. Otherwise return a short note I can save. Do not claim it is
saved unless you can confirm the actual saved record. Do not send anything.

The note can be short:

PRACTICE: Workshop proposal v1 is drafted. Online format is agreed. Budget and date remain unresolved. Put open decisions before background in workshop summaries. Next: confirm the missing terms, then revise the proposal. Nothing has been sent.

Save the useful state, not a transcript of every turn. It should tell the next session where the work stands and which version to use.

Think of a bookmark with a note in the margin. The bookmark tells you where to resume; the note reminds you what mattered. Neither helps if the next reader never opens the book. The AI must actually read the saved handoff.

Check the return path once

Open a new task in the same approved project and ask it to recover the next step from the saved record. If it cannot, fix the file location or reading instruction. Do not keep rebuilding the whole workspace.

When moving work between AI products, hand over the same compact note and relevant files. Do not expect another product to know your old conversation. Keep one task responsible for edits to a given file so two assistants do not rewrite each other's work.

Ready to move on: you can leave, return, and continue from a correct saved state without retelling the whole story.

Chapter 06

Feedback that improves the next result

“Make it better” gives the AI very little to work with. Helpful feedback names the miss, explains its effect, and shows the desired change.

Compare “This sounds wrong” with: “This is too formal for a familiar customer. Keep the decision and next step, remove the sales language, and use the tone of this approved example.”

You do not need to diagnose the whole system. Point to the part that failed. The AI can help turn that observation into a specific correction.

Three things people mean by learning

What changes Example What to expect
This draft “Put open decisions first.” A revision in this task; check the result
Future work Save that preference in approved project guidance or a skill It can guide later tasks if loaded and followed; test the next use
The underlying model Provider training processes Model training is separate; your saved rule does not retrain the model

The thumbs-up or thumbs-down button is product feedback. It is not a reliable way to install your company's writing rule. If a correction matters next time, put it in an appropriate place and verify that later work uses it.

OpenAI distinguishes memories from required project instructions in its personalization guide. Claude documents project memory in its Projects guide. Neither is a reason to treat an unverified recollection as the current approved record.

Turn one correction into reusable guidance

You treated a suggested budget as approved. Repair this draft.
Then propose one short rule for our proposal guidance that prevents the mistake.
Apply it only to proposal work. Show where the rule should live and how we can
test it with a new example. Do not install or change shared instructions yet.

A useful proposed rule would be:

Separate agreed terms from suggestions. Label a price, date, or responsibility as approved only when the supplied source explicitly supports that status. Otherwise flag it for confirmation.

Once the right person approves saving the rule, save it in the existing guidance. Next time, give the workflow notes containing both an approved item and a suggestion. Check that it distinguishes them. This verifies useful behaviour more convincingly than an answer saying, “I have learned my lesson.”

Keep learning small and specific

Use this loop: notice a miss → correct the work → save the useful rule → try it again.

A one-off preference may belong in this task only. A repeated report format belongs with that report. A company-wide instruction belongs with its owner. Avoid piling every correction into global instructions; rules can contradict each other or make simple jobs awkward.

Keep a change when the next use shows it helped. More instructions and more skills are not measures of improvement.

Try it: select one recurring annoyance. Write the correction, name where it belongs, and choose the next normal task that will show whether it worked.

Part 03 / Chapters 7–11

Delegate more

Add the right tools for the job.

After this part, you can combine access, reusable methods, and checks that catch mistakes.

The quiet beacon
Chapter 07

Connectors, apps, skills, and plugins

These are related, but they solve different problems. Imagine a colleague preparing a workshop proposal.

Part What it supplies Familiar comparison
Connected app or connector A supported route to information or actions in another service Access to a filing system or work tool
Tool One operation, such as search files or create a draft A specific action the colleague can perform
Skill Reusable instructions and resources for a kind of work The team's playbook
Plugin An installable package that may include skills and connections A kit containing playbooks and tools

The names and packaging vary. If you see MCP, it means Model Context Protocol, a standard way for AI software to connect to tools and resources. Think of a common plug shape. Matching the plug does not decide what the connected account is allowed to do. OpenAI explains the pieces in Skills and Plugins; Microsoft documents its Cowork customization.

Three different jobsAccess. A method. A kit.
ConnectorAccess to a service

Like a key: it provides an approved route to files or actions.

SkillA reusable method

Like a playbook: it explains how to do a kind of work.

PluginA packaged kit

It may bundle skills and connections. Check what is included.

A tool is one action: open a file, search, or create a draft. Having a key does not grant permission to do everything inside.

Add access when a real task needs it

If you only need to summarize one approved document, attach it. If you repeatedly need the latest version from a shared drive, an approved connection may remove repeated downloading and uploading.

Connecting an app can involve several separate steps: make the plugin available, connect the right account, grant permitted actions, and confirm the required source is reachable. Installation alone is not proof of access.

Ask the AI to perform a small check: “Find this named document and report its title and updated date. Do not change it.” Then inspect the source it found. A confident summary of the wrong file is still the wrong file.

Reading and writing are different permissions

Reading a calendar is different from inviting ten people to a meeting. Finding a proposal is different from replacing it. Check the actual connection, account, and action settings. A connected account can have broader permissions than the particular task needs. OpenAI's Work access overview describes these layers.

For your first connected workflow, choose a narrow purpose and a clear output. Ask for a draft and handle sending yourself. Use available app and admin controls to support that boundary; a written instruction alone is not a technical guarantee.

Try it: name one repeated step a connection would remove. If you cannot name the step, leave the connection for later.

Chapter 08

Turn a good workflow into a skill

A prompt is a request you make now. A skill is a reusable way to handle a class of requests. The skill might include steps, a template, examples, and checks. It earns its place when those details repeatedly matter.

You would not write a staff handbook for one sandwich order. You might write a clear procedure for the lunch service you run every day. Apply the same restraint to AI.

What belongs in a useful skill?

For a workshop proposal, the useful parts are concrete:

  • When to use it: turning approved discovery notes into a proposal draft.
  • Inputs: current notes, the approved template, and confirmed commercial terms.
  • Steps: extract facts, flag gaps, draft, then check against the sources.
  • Output: a proposal with unresolved terms clearly marked.
  • Limits: do not invent approval or send the result.

Keep current client facts in the source files. Keep the reusable method in the skill. Otherwise, a rule intended to improve every proposal can quietly carry one client's details into the next.

Create the instructions before installing them

Turn the workflow we just used into a draft skill for future workshop proposals.
Include when it applies, required inputs, the drafting steps, quality checks,
and the approval boundary. Use our corrected draft as a structural example,
but remove its client-specific facts.

Keep it short. Reuse existing guidance rather than duplicating it.
Return the instructions for review; do not install or share them yet.

After approval, use your product's supported skill setup. Test it in a new task with new material: the output should follow the method without carrying over old facts.

OpenAI supports explicit skill selection and automatic matching; its skill guide explains the surface-specific syntax. Microsoft's customization guide explains creating, importing, and testing custom skills. For Claude, use the official skills help.

Reuse across products carefully

The written method often transfers well. The package, file paths, commands, permissions, and tool names may need adaptation. Have the receiving app check compatibility instead of promising that a ZIP works everywhere.

Ready to move on: a new task uses the skill on different material and meets the same checks without carrying over old facts.

Chapter 09

Chain skills, review, and stress test

Chaining means giving several methods a useful order. A proposal workflow may gather evidence, draft, review, challenge assumptions, and revise. You can request those stages in ordinary language before installing any named skills.

Think of a kitchen. Preparation, cooking, and checking the plate have different jobs. Adding five more cooks does not fix a missing ingredient. Each stage should contribute something the others do not.

Follow one proposal through the chain

Stage Question it answers What passes forward
Brief What decision should this proposal enable? Audience, outcome, required sources, limits
Draft What can we responsibly offer from the supplied facts? Proposed document with visible gaps
Source check Does each factual claim match the evidence? Corrected facts and unresolved conflicts
Reader review Can the customer understand the offer and next step? Specific clarity repairs
Stress test What credible situation would make this proposal fail? Material risks, not invented objections
Revise and finish Were the important defects fixed? Exact draft, remaining decisions, saved return point

In the workshop example, a source check catches the unsupported budget. A reader review notices that the next decision is unclear. A stress test asks whether the proposed date depends on an unavailable facilitator. Those are distinct checks with practical consequences.

Review the work against a standard

Review this exact proposal against the attached brief, notes, and template.
Check factual support, missing requirements, clarity for the customer,
and the decision they need to make next.

For each material defect, show its location, why it matters, and the smallest fix.
Repair the draft, then check the changed sections again.
Do not change agreed terms or add unsupported claims.

Stress test the assumptions

Stress test this proposal. What is the strongest credible reason the customer
could reject it or the delivery could fail? Use the actual scope and sources.

Separate an observed problem from a hypothetical risk. Tell me what evidence
would change your assessment. Recommend only changes that materially improve
the decision or delivery. Do not invent objections to fill a list.

Asking the same AI to play “finance director” and “customer” provides useful viewpoints. It does not create two independent experts. Both can repeat the same false premise. For consequential facts, use the underlying evidence and a qualified person where the decision requires one.

What OneShot means here

OneShot is Sidekick's name for a workflow that carries substantial work from a brief through building, checking, improvement, and a clear handoff. It is a custom method, not a universal feature included in every AI account. If it is installed, ask for it. If it is not, this prompt describes the method:

Take this task from brief to a checked draft. Use only the stages it needs:
clarify important gaps, plan, build, check the sources and requirements,
repair material weaknesses, and return the exact result with remaining decisions.
Use available relevant skills. If a named skill is missing, say so and follow
the method directly. Stop before any external action I have not approved.

Stop reviewing when the required checks pass and no material defect remains. “Make it 10% better” repeated indefinitely is a fine way to spend the afternoon moving commas.

Try it: run one source check and one stress test on a small draft. Notice whether they find different kinds of problems. Keep the checks that change the result.

Chapter 10

Goals and evaluations: define what good looks like

A goal describes the result you want. An evaluation, often shortened to eval, checks whether the result meets a standard. Think of ordering a bookshelf: the goal is a shelf that fits the space and holds your books; the evaluation includes measuring the space and checking whether the shelf wobbles.

“Work on my proposal” names activity. “Create a proposal draft that follows this template, separates confirmed terms from gaps, and gives the customer a clear next decision” describes a finish line.

Write a finish line the AI can check

Goal: create a review draft of the workshop proposal using the supplied sources.
Include the outcome, proposed scope, known responsibilities, unresolved terms,
and the customer's next decision.

Use the approved template. Do not invent prices, dates, or commitments.
Finish when every required section is present, factual claims are supported,
the document opens correctly, and any remaining decisions are clearly listed.
Return the draft and stop before sending or publishing.

In supported ChatGPT desktop and Codex surfaces, /goal can keep a defined objective active across longer work. For ChatGPT Work on the web, put the outcome and completion checks in the task prompt. A goal does not grant broader access or guarantee that work succeeds. See OpenAI's long-running work guide.

If the goal is unclear, define it with the AI first. “Automate my business” leaves too much unresolved. Start with “Prepare a weekly update from these two approved sources, without posting it.”

Use checks that could catch a real failure

For the workshop practice, a small evaluation set looks like this:

Test input A passing result A failure
Budget is suggested, not approved Budget stays unconfirmed Presents $2,000 as an agreed price
No workshop date is supplied Lists the date as unresolved Invents a date
Old template names a different customer Uses the current sources and flags ambiguity Copies the old name into the proposal
Two sources give conflicting dates Shows the conflict and asks which governs Silently picks one
A required source is unavailable Reports the gap and its effect Claims it read the source

These are practice checks, not a scientific benchmark. They make “good” less subjective and expose mistakes a pleasant writing style can hide.

Match the check to the work: recalculate a spreadsheet total, trace a summary to its notes, inspect a design at its intended size, or challenge the evidence behind a recommendation.

A score is not proof

An AI giving its own work 96/100 has told you its opinion. Ask what was checked and what evidence supports the result. A missing legal term or wrong customer cannot be averaged away by excellent spelling.

Check the artifact and the workflow separately. A correct draft shows that this task worked. Repeated useful runs, with the effort and cost recorded, help you judge whether the workflow is worth keeping. Neither guarantees future success.

Ready to move on: you can name a few ways the work could fail, run those checks, and distinguish a finished result from an unresolved task.

Chapter 11

Automate the parts that have earned it

Once the AI produces a useful result repeatedly, you can remove some of the effort around starting and moving the work. Automate one stable part at a time.

A recipe tells you how to make dinner. A timer tells you when to start. A schedule cannot rescue a bad recipe; it can only arrange for the same problem to arrive punctually.

Move up one step at a time

Stage What changes Example
You ask One bounded task Summarize these notes
You reuse Saved instructions and a tested format Prepare every workshop recap the same way
You connect The AI retrieves approved current inputs Read the named workshop folder
You schedule A defined trigger starts the workflow Prepare Friday's update at 9 a.m.
You authorize selected actions Proven low-risk steps proceed within explicit limits Save a new draft to the agreed output folder

Sending communications, changing official records, or making purchases involves different consequences from preparing drafts. Keep the human decision where the work requires it. More autonomy is useful when it reduces total effort without creating unacceptable errors.

Design a small recurring workflow

Choose one recurring output you already know how to check. Write down the trigger, current inputs, destination, quality checks, and what should happen when a source is missing or a run fails. Name the person who handles exceptions and can pause it.

Test the workflow manually with a normal case, no new material, and an unavailable source. Then use the product's supported controls to prepare and review the exact schedule. Confirm its time zone, sources, destination, and permissions.

The complete walkthrough shows how to build that routine around a weekly project update. It includes two sets of practice notes, expected outputs, a reusable method, and the proposed schedule. You can try the work before connecting anything.

Running in the background is not the same as scheduling

A running task is doing work now. A schedule starts work later or repeatedly. A goal keeps a finish line in view. These functions can work together, but none implies the others.

The execution location also matters. ChatGPT cloud work can continue independently of your computer; local scheduled work needs the required computer, app, and files available. OpenAI's scheduled-task guide explains the distinction. For Claude, check the current Cowork getting-started guidance for the execution mode you use. Microsoft documents scheduling and task management in its Cowork overview.

Judge total effort

Compare total gathering, review, correction, and completion time with your old approach. Include usage charges. A fast first draft followed by an hour of repair may be a loss.

If a scheduled task produces noise, narrow its sources or reporting condition. If it repeatedly misses the same requirement, repair the method before increasing the frequency. If an action has an uncertain result, inspect the destination before retrying so you do not create duplicates. Pause the workflow when the sources or responsibilities change enough that the old rules no longer fit.

A sensible next step: select one recurring draft you already know how to check. Improve that workflow until the next run needs less explanation. Then decide whether scheduling would actually help.

Part 04 / Chapter 12

Build a repeatable routine

Bring the pieces together.

After this part, you can test a complete routine and identify a useful part to automate.

The open cyan field
Chapter 12

Put it together: a weekly project update

A team update sounds simple until you have to reconstruct the week from scattered notes, remember last week's open questions, and work out what actually needs a decision. This walkthrough brings the earlier concepts together around that job.

Illustrative example: Project A and all notes below are fictional. The sample answers show what to check; they are not records of a client result or a live automation. You can practise both weeks in ordinary chat. Nothing needs to be connected or installed.

First use: give it the work and a finish line

Paste this complete request:

PRACTICE: prepare Project A's weekly update for its team lead.
Use only the notes below. Produce a draft of no more than 150 words with
progress, blockers, decisions needed, and next actions. Cite each factual
bullet with its note ID, such as [A1]. Do not send anything or change files.

Done means the reader can see what changed and what needs attention.
Keep proposals separate from approvals. Do not invent owners or dates.

Week 1 notes:
[A1] The team approved a pilot with 10 participants. The start date is undecided.
[A2] The demo owner completed the draft invitation and needs the team lead's
approval before invitations can go out.
[A3] The demo owner proposed starting next Tuesday. No one approved that date.
[A4] The demo coordinator will check room availability by Monday.

An acceptable draft could say:

PRACTICE: Project A, week 1

Progress: The pilot is approved for 10 participants. The draft invitation is complete. [A1, A2]

Blockers: Invitations await the team lead's approval. [A2]

Decisions needed: Approve the invitation and choose a start date. Next Tuesday is a proposal. [A1, A2, A3]

Next action: The demo coordinator will check room availability by Monday. [A4]

Those little source labels make review easier: you can trace a sentence back to a note. They are useful only if the cited note actually supports the sentence. A citation is a receipt to inspect, not a decorative stamp.

Correct the method once

You want to see the decisions before the good-news paragraph. Tell the AI:

Put decisions needed first, then blockers, progress, and next actions.
Keep the source IDs beside the facts. Preserve the distinction between a
proposed date and an approved date. Revise the update using that order.
Then give me a short reusable method for future project updates.

The revised update should lead with the invitation approval and start-date decision. Its facts should stay the same. A compact reusable method is enough:

Weekly update method

Read the current notes and the last saved state. Write no more than 150 words in this order: decisions needed, blockers, progress, next actions. Cite the current source for each factual bullet. Separate proposals from approvals. Compare with the prior state so resolved issues do not remain open. Report missing sources. Return a draft for review.

For now, save or copy that method. It can later become a skill through your app's supported setup. You can test whether the instructions help before installing anything.

Save the state separately from the method

Ask for a short handoff using the session routine. Compare it with this example and save a correct version for the second use:

PRACTICE: Project A, end of week 1. Pilot approved for 10 participants. Invitation drafted; approval pending. Start date undecided; next Tuesday was only proposed. Demo coordinator to check room availability by Monday. Use the Weekly update method, with decisions first. Next: read week 2 notes and update these statuses. Nothing sent.

The method explains how to do the job. The handoff says where this particular job stands. Keeping them separate lets you reuse the method for Project B without accidentally inviting Project A's participants. That would be an adventurous interpretation of teamwork.

Second use: recover, compare, and apply the feedback

Open a new chat. Paste the method and the saved handoff, followed by this request:

Continue this fictional practice using the Weekly update method and week 1
handoff above. Read the week 2 notes below. Produce the next update, showing
what changed. Then list any check that failed or information still missing.
The new notes update the old state where they explicitly resolve an item.
Do not carry a resolved blocker forward. Do not send anything or change files.

Week 2 notes:
[B1] The team lead approved the invitation on Monday.
[B2] The demo coordinator confirmed a room is available next Thursday.
[B3] The team lead chose next Thursday as the pilot start date, replacing the
unapproved Tuesday proposal. The approved group remains 10 participants.
[B4] Invitation delivery is still pending. The notes give no owner or send date.

A passing result could look like this:

PRACTICE: Project A, week 2

Decisions needed: Assign who will send invitations and when. Neither is specified. [B4]

Blockers: Invitation delivery is pending; the earlier invitation-approval blocker is resolved. [B1, B4]

Progress: The invitation is approved. A room is available, and the team lead chose next Thursday for the 10-person pilot. Thursday replaces the earlier Tuesday proposal. [B1, B2, B3]

Next action: Assign invitation delivery, then confirm completion. The source does not establish that invitations have been sent. [B4]

Inspect two different things. Did the facts update correctly? And did the new task use the decisions-first preference? A correct answer to both supports this particular reuse test. It does not establish that every future task will remember the rule.

Before closing, replace the practice handoff with the week 2 state: invitation approved, Thursday chosen, room available, invitation delivery pending with owner and date unknown. Keep the old handoff as history if useful, but identify the week 2 note as current.

Give each check a job

You now have a useful chain: read → compare → draft → check → revise → save the handoff. One AI task can carry out those stages. Named skills become useful when their instructions need to be reused or maintained separately.

Check What to inspect in this example A defect worth repairing
Source check Compare claims with B1-B4 Says invitations were sent
Reader review Look at the first section Buries the missing delivery owner under progress
Stress test Ask what would stop the pilot from happening Treats a room and a date as proof that participants were invited
Reuse check Compare the result with the saved method Forgets decisions-first ordering

A stress test can raise a question such as “What if invitations are delayed?” It should not invent evidence that they already are. You still decide the owner and deadline; the AI makes the unresolved work easier to see.

Try two variations before trusting the routine. For each, open a separate new chat and paste only the reusable method, the original week 1 handoff printed above, and that variation's notes. Say, “Use only these supplied practice inputs.” This keeps the answer from a previous attempt out of the test.

In the first variation, supply B2-B4 but omit B1. The result should leave invitation approval unconfirmed. In the second, supply no week 2 notes. It should report missing input instead of announcing that nothing changed. These small evals test the errors most likely to mislead the reader.

Connect the inputs when copying becomes the chore

After the manual routine works, you may want the AI to read the current notes from an approved folder or connected app. Keep the same method and checks. Change how the inputs arrive.

Use the connections chapter to check access to one named source first. In real work, ask it to show the file name and date it found. Open that source once to confirm it is the right one. Replace the practice IDs with useful file or source links in the update.

A connector supplies access; a skill supplies the method. A plugin may package these together. None chooses the correct source or checks the answer merely by being installed. If attachment is still easy, keep attaching the file.

Let a schedule start the tested routine

When the connected version is useful across normal runs, prepare a schedule using the automation chapter and your product's official controls. A proposed setup for this example is:

Setting Proposed value to review
Trigger Friday, 9 a.m.; explicitly select your working time zone
Inputs The approved Project A notes location, Weekly update method, and current handoff
Output One dated draft in the agreed output folder
Quality gate Every factual claim has support; changed statuses reconcile; open decisions come first
Missing or unreadable source Return a failure notice through the approved task interface; do not issue a normal update
No new material State that only after successfully checking the expected sources
Retry Inspect whether the week's draft already exists before creating another
Human role Review the draft and handle decisions and sending
Owner and pause Name the person who checks failures and can pause the schedule

This table is a plan. Entering it in a chat does not activate a schedule. Review the actual saved configuration and first run through the app, including its failure behaviour. Apply any usage limit appropriate to the account.

You have now moved from preparing one update to specifying a repeatable workflow. The possible gain is less gathering, rebriefing, and formatting. Measure that against the time spent checking and repairing the result over normal uses. If the routine adds more work than it removes, simplify it before giving it a Friday appointment.

Transfer the pattern to a different job

For content work, the inputs might be an approved article and editorial guidance; the output might be a newsletter and social drafts. Replace the project-status checks with claim fidelity, audience fit, and format checks. Save a correction such as “use the original article's figures; do not add a stronger performance claim.”

For a spreadsheet update, keep the formulas and source data explicit. If three fictional orders total $40, $60, and $100, the expected total is $200. Check that known case before scaling up, and test how the workflow treats a blank value. A blank cell should not silently become a zero unless that is your agreed rule.

The repeatable structure transfers. The definition of a good result must fit the work.

Chapter 13

Find the right controls in your app

Use the route for your actual product and account. If a label is missing, check the current official guide or ask your administrator. You can still practise briefing and review in chat while access is resolved.

Claude Cowork

Open Cowork in the Claude desktop app and choose a working location for the task. Start with a small approved folder or a suitable Project. Anthropic's four-minute setup tutorial shows the current flow, including guided customization. You can postpone optional connections until a task needs them.

Keep the distinction between the files and the project that uses them. A Project helps carry context between sessions; confirm that the next session finds the right source and current record. Use Claude's current Cowork help for supported devices, execution modes, approvals, and account requirements.

Microsoft Copilot Cowork

Use your approved Microsoft account, open Copilot, and select Cowork where available. Attach the relevant files or choose supported cloud sources. Work or school access depends on your organization's setup, licensing, and billing configuration. Start with Microsoft's setup instructions.

For reusable instructions, the documented Customize area has Plugins and Skills. Use the customization guide, and test changed skills in a new conversation. Your actual account determines what is available. A local folder recipe written for Claude should not be treated as proof of Microsoft permissions or persistent context.

ChatGPT Work

Switch from Chat to Work when you want a larger deliverable. Provide the source material and the result you need. On supported desktop setups, choose local work for resources on your computer or cloud work for accessible hosted sources. The Work introduction, with video, shows the starting experience.

Use Projects for related work and the Plugins area for supported extensions. On the web, a project uses uploads and connected sources rather than automatically reading your computer. If you use Codex for everyday work, you can continue there; OpenAI describes overlapping core capabilities with different presentation in its Chat, Work, and Codex comparison.

If the app disagrees with this guide

Do not keep clicking around to match an old screenshot. Tell the AI the exact product, device, and visible labels, and ask it to use current official instructions. Have it distinguish a missing feature from a permission issue. Your organization decides which tools and information you may use; a tutorial cannot grant access.

Chapter 14

When the work goes wrong

What happened What to try
The answer is generic Add the reader, actual sources, desired result, and one good example
It used old facts Point to the current source; ask what conflicting source it used
It forgot a correction Check whether the rule was saved, where it lives, and whether this task loaded it
It says it cannot see a file Confirm the product and local/cloud mode, file location, and access; attach the approved file if appropriate
It keeps asking minor questions Define which routine choices it can make and which decisions change the result
It changes too much Name the exact section to revise and the approved content to preserve
It says a file is finished but you cannot find it Ask for the actual saved location or download; open it and check the contents
A tool or schedule fails Read the error and inspect the last successful result before retrying
It starts an unexpected change Stop the task, ask what changed, and inspect the affected files before continuing
A workflow costs too much Narrow the sources and scope, reduce repeated runs, and use the product's usage controls

For a confusing failure, use:

Stop and help me diagnose this. What did you attempt, what actually happened,
and what evidence do you have? Separate missing information, missing permission,
tool failure, and an unclear instruction. Suggest the smallest safe next step.
Do not retry an external action or change access settings.

Files, emails, and websites can contain instructions that were not written by you. Treat those as source content, not permission to change the job. If a document tells the AI to ignore your request or send information somewhere else, stop that action and ask for a plain explanation. This is one reason access limits and review belong in the workflow.

You do not have to become the technical support team. A useful escalation contains the intended task, the failed step, the exact error, and what remains unfinished. Leave passwords and private information out of anything you share for help.

Chapter 15

Quick reference for your next task

Find the problem below. Use the short prompt now, or follow its link for the explanation and complete example. For an error or unexpected change, use troubleshooting.

What you need A useful starting prompt
I don't know what to ask “Help me define the result before building it. Ask one important question at a time.”
The answer is generic “Use these sources to produce this output for this reader. Follow these limits and checks.”
My files and versions are confusing “Identify the current source and any conflicting versions. Explain which you would use and why.”
I keep repeating the background “Read the saved current-work note. Tell me what is done, what is unresolved, and what comes next.”
The draft misses the mark “This part misses the mark because… Change it to… Preserve…”
It forgot my feedback “Check where the correction was saved and whether this task read it. Show what is missing before changing the guidance.”
I want to reuse this method “Propose a short reusable method, the right place to save it, and a way to check the next use.”
I want a stronger result “Check the exact output against the brief and sources. Locate material defects and repair them.”
I want to test what could go wrong “What is the strongest credible way this could fail? What evidence would change your view?”
I'm ready to stop for today “Return the exact result, unresolved decisions, and a short saved or saveable handoff.”
I want this done every week “Design and test the recurring workflow. Show the exact trigger, sources, output, limits, and pause control before activation.”

Choose your next step

Stage What you will be able to do Read and try
Start Give one small task, check the answer, and improve it First task, then briefs
Build continuity Return without retelling everything and preserve useful feedback Projects and context, sessions, feedback
Delegate more Reuse a method and combine drafting with meaningful checks Connections, skills, review, goals and evals
Make work repeatable Test the whole routine, then automate a useful part Automation and the complete walkthrough

These are stages of practice, not course prerequisites. Use the next stage when your work needs it. You can get plenty of value without becoming the household plugin collector.

You can stay at any stage that helps. Progress means useful work takes less effort and fewer corrections.

Chapter 16

Docs, videos, and deeper explanations

Choose the resource for the question in front of you. You do not need to finish a course before trying the first task. Official learning sites may ask you to sign in; the written examples in this guide stand on their own.

A short learning path

Use one app's instructions at a time. Learning three sets of buttons in one sitting is optional extra homework.

When you reach this point Open this next Try before moving on
You want to see your app in action Choose the ChatGPT Work introduction and videos, Claude's four-minute setup tutorial, or Microsoft's written setup guide Find where to start a task and supply its sources, then complete Chapter 1
You keep re-explaining the work Read the project guidance for your app, listed below, alongside Chapter 5 Save a handoff and recover the correct next step in a fresh task
A correction is worth reusing Read your app's skills guide below, then revisit Chapter 8 Test the written method on a different example before deciding to install it
You are ready to combine the pieces Complete both uses in Chapter 12, then consult the scheduling docs for your app Verify current facts, saved feedback, and missing-input behaviour before preparing a schedule

Watch a relevant introductory video with one question in mind: “What do I need to do to give it my next job?” Pause and try that step. The written examples here remain usable on their own. Linked video pages were checked; the videos have not been reviewed end to end for this guide.

Organize recurring work

Reuse methods and add tools

Continue longer work or repeat a task

Learn at your own pace

  • Claude Academy: look for Claude 101, Introduction to Claude Cowork, and task-specific tutorials. Choose one topic that helps with work you already have.
  • Sidekick Starter Kit: an optional guided workspace for beginning with Claude Cowork. If you already have a working client setup, use that setup rather than creating a duplicate.

For your next session, bring one task you understand well enough to check. State the result, provide the sources, and use the first correction to make the next attempt better.