# AI Teachers — ChatGPT Work: Your AI Chief of Staff Updated 2026-10-25 · Free written training workbook Use invented or permitted data. Your AI tool may require a separate subscription. Download this workbook and save answers locally; this course site saves only completion checkmarks. ## The outcome Build a weekly executive briefing practice using ChatGPT Work and only the sources and actions you explicitly approve. ## What you will learn - Differentiate Chat, Work and Codex - Create a supported research pack - Use connected data deliberately - Prepare executive deliverables - Add review and recurrence carefully ## Lesson 1: Define the chief-of-staff job (25 min) Start with the result you need, not an ambiguous command to 'run my day'. ### Follow these steps 1. In eligible ChatGPT accounts, select Work; otherwise draft the workflow in Chat with fictional notes. 2. Choose the fictional weekly leadership brief as the task. 3. Define the decisions supported, audience, output format, time period and exclusions. 4. Agree on permissions: review-only first, no sending or meeting changes. ### Copyable prompt Act as a chief-of-staff analyst for a fictional founder. Prepare a Friday brief from the notes I will supply. Provide wins, unresolved decisions, deadlines, risks, and the three questions I should ask Monday. Mark missing facts; don't access or modify outside tools unless separately approved. ### Deliverable Written chief-of-staff role charter and requested deliverables. ### Quality gate The instructions are limited enough to assess objectively. ### Watch out ChatGPT Work, Codex and other tool access vary by plan and workspace. My result: What I verified: What I will change: --- ## Lesson 2: Research and verify a decision brief (30 min) Decision-grade analysis requires dated sources and explicit assumptions. ### Follow these steps 1. Choose one question: what changed this week in our fictional launch project? 2. Supply a source pack with dates; request a comparison against the prior week. 3. Ask for evidence, conflicts, missing data and confidence qualifiers. 4. Independently inspect at least three assertions before including them. ### Copyable prompt Review these fictional project documents and compare current week to prior week. Separate facts directly supported by sources from inferences. For every important change provide the source and date. Identify unanswered questions, contradictory dates, and the next human decision. Do not invent metrics. ### Deliverable A source-backed executive brief with a verification checklist. ### Quality gate The brief can be audited back to source material. ### Watch out Treat AI-generated source labels as claims until you open the documents yourself. My result: What I verified: What I will change: --- ## Lesson 3: Connect the right information (25 min) Connectors are useful but should not silently broaden the workflow's scope. ### Follow these steps 1. List the minimal calendar, file, or CRM data this brief actually needs. 2. Inspect linked app permissions and available read/write actions before connecting anything. 3. Try the workflow with a manually provided fictional dataset first. 4. If permitted, compare the connected result with the known source record and remove unnecessary access. ### Copyable prompt For a weekly brief, suggest the least-privilege source plan using the documents and events I specify. Tell me which actions are read-only, which modify data, and which require approval. If a requested source is inaccessible, mark it MISSING and continue using only permitted material. ### Deliverable A source and permissions map plus a no-access fallback. ### Quality gate No external state is changed without explicit permission. ### Watch out A connected app is not proof that every underlying record is available or current. My result: What I verified: What I will change: --- ## Lesson 4: Produce a finished executive package (30 min) A chief of staff earns trust by finishing the deliverable and exposing its assumptions. ### Follow these steps 1. Request a one-page memo and a concise action table from the verified pack. 2. Set formatting and naming requirements; avoid invented references. 3. Ask Work to separate confirmed milestones from proposals. 4. Review deliverables, numbers, citations, names and date consistency. ### Copyable prompt Using the verified fictional status pack, create a one-page leadership memo and a table with decision, owner, deadline, source and status. Add an executive summary, an exceptions section, and a draft Monday agenda. Every entry must be tied to a source or labeled PROPOSED. Do not send, schedule or publish. ### Deliverable An executive memo, task table and agenda draft. ### Quality gate Every proposed action has an owner and an approval step. ### Watch out Only treat files as completed when you have opened and inspected the saved output. My result: What I verified: What I will change: --- ## Lesson 5: Create a reviewed operating rhythm (30 min) The final system should be resilient and easy to hand off. ### Follow these steps 1. Write a repeatable Friday checklist with trigger, sources and stop conditions. 2. Test what happens when the calendar is empty or files disagree. 3. Measure preparation time, correction time and useful decisions. 4. If scheduling is supported, start with a reminder or draft-only task and monitor its results. ### Copyable prompt Write an operating procedure for a weekly Friday chief-of-staff review. Include approved inputs, trigger, outputs, read/write permissions, owner sign-off, audit trail, exception handling, and an evaluation rubric for factual accuracy, completeness and usefulness. ### Deliverable A tested weekly runbook and two realistic exception tests. ### Quality gate The workflow can fail safely and signal that human follow-up is needed. ### Watch out Never assume an unattended task performed an external action unless logs or records confirm it. My result: What I verified: What I will change: --- ## Final review - [ ] Every material fact has a permitted source. - [ ] Missing data is visible. - [ ] External actions still require authorized approvals. - [ ] I have tested at least one failure case. - [ ] I know who owns the result and how to stop the workflow. Official reference links: - ChatGPT Work and Codex: https://help.openai.com/en/articles/20001275-chatgpt-work-and-codex AI Teachers · https://aiteachers.cc/academy/chatgpt-work-chief-of-staff/