ChatGPT Work: Your AI Chief of Staff
Research, documents, connected apps and executive-ready delegation.
Build a weekly executive briefing practice using ChatGPT Work and only the sources and actions you explicitly approve.
2–3 hours suggested practice · Free, written and self-paced · No certificate or video promised
Your learning outcomes
- Differentiate Chat, Work and Codex
- Create a supported research pack
- Use connected data deliberately
- Prepare executive deliverables
- Add review and recurrence carefully
0 of 5 activities checked
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Define the chief-of-staff job
Start with the result you need, not an ambiguous command to 'run my day'.
Follow along
- In eligible ChatGPT accounts, select Work; otherwise draft the workflow in Chat with fictional notes.
- Choose the fictional weekly leadership brief as the task.
- Define the decisions supported, audience, output format, time period and exclusions.
- Agree on permissions: review-only first, no sending or meeting changes.
Written chief-of-staff role charter and requested deliverables.
Copy and adapt this 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.The instructions are limited enough to assess objectively.
Remember: ChatGPT Work, Codex and other tool access vary by plan and workspace.
Research and verify a decision brief
Decision-grade analysis requires dated sources and explicit assumptions.
Follow along
- Choose one question: what changed this week in our fictional launch project?
- Supply a source pack with dates; request a comparison against the prior week.
- Ask for evidence, conflicts, missing data and confidence qualifiers.
- Independently inspect at least three assertions before including them.
A source-backed executive brief with a verification checklist.
Copy and adapt this 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.The brief can be audited back to source material.
Remember: Treat AI-generated source labels as claims until you open the documents yourself.
Connect the right information
Connectors are useful but should not silently broaden the workflow's scope.
Follow along
- List the minimal calendar, file, or CRM data this brief actually needs.
- Inspect linked app permissions and available read/write actions before connecting anything.
- Try the workflow with a manually provided fictional dataset first.
- If permitted, compare the connected result with the known source record and remove unnecessary access.
A source and permissions map plus a no-access fallback.
Copy and adapt this 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.No external state is changed without explicit permission.
Remember: A connected app is not proof that every underlying record is available or current.
Produce a finished executive package
A chief of staff earns trust by finishing the deliverable and exposing its assumptions.
Follow along
- Request a one-page memo and a concise action table from the verified pack.
- Set formatting and naming requirements; avoid invented references.
- Ask Work to separate confirmed milestones from proposals.
- Review deliverables, numbers, citations, names and date consistency.
An executive memo, task table and agenda draft.
Copy and adapt this 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.Every proposed action has an owner and an approval step.
Remember: Only treat files as completed when you have opened and inspected the saved output.
Create a reviewed operating rhythm
The final system should be resilient and easy to hand off.
Follow along
- Write a repeatable Friday checklist with trigger, sources and stop conditions.
- Test what happens when the calendar is empty or files disagree.
- Measure preparation time, correction time and useful decisions.
- If scheduling is supported, start with a reminder or draft-only task and monitor its results.
A tested weekly runbook and two realistic exception tests.
Copy and adapt this 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.The workflow can fail safely and signal that human follow-up is needed.
Remember: Never assume an unattended task performed an external action unless logs or records confirm it.
Keep your work. Use it again.
Test the workflow on a second example before connecting accounts or automating. If you need feedback on a real project, bring your sanitized brief to a private working session.
All five activities checked. Revisit the quality gates on a fresh example to validate your work.
Product documentation and next steps
Tools and plan entitlements can change. Check your provider and workspace access before following interface instructions.
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Updated 2026-10-25. Paid group cohorts, certification, and live dates are not represented as currently available.