CEOs and founders
Board and investor updates from your own numbers, decision briefs from a reading pack, a weekly business review, a competitor watch that runs itself, a company AI policy and adoption cadence, an honest way to measure AI ROI, and what never to delegate.
For CEOs, founders, managing directors and general managers
Better decisions and clearer updates, with the judgment and the signature still yours
- Board and investor updates drafted from your data pack, with every number traced to its source
- Decision briefs that lay out the options, the evidence and the strongest case against your favourite
- A weekly business review pre-read waiting before the meeting, with the questions for each owner
- A weekly competitor digest where every item links to a primary source
- A one-page AI policy and a quarterly adoption review the whole company understands
- AI spend judged on measured outcomes, not seat counts or self-reported time saved
On this page
- Where AI helps in this job
- Start in 15 minutes
- The tools CEOs use
- Members only: Workflow: the board and investor update
- Members only: Workflow: a decision brief from a reading pack
- Members only: Workflow: the weekly business review
- Members only: Workflow: a company AI policy and adoption cadence
- Members only: A skill for CEOs
- Members only: Guardrails and hooks
- Members only: Routines that run without you
- Members only: Prompt ladder for CEOs
- Members only: Measure it
- Members only: Risks and what not to delegate
You do not need to become a prompt engineer. You need three habits: give the model your own documents instead of asking it what it knows, make it show where every number came from, and keep every decision and every signature yourself. This page turns those habits into workflows for the work you repeat every week and month, and gives your company a policy and a way to measure whether AI pays.
Where AI helps in this job#
| Task | What AI does well | What you still own |
|---|---|---|
| Board and investor updates | Drafts the update from your KPI export, finance summary and notes, in last month's format | Every number, the tone, and what you disclose |
| Decision briefs | Turns a reading pack into options, evidence and risks, and argues the other side | The decision |
| Weekly business review | Builds the variance table and the question for each owner | Which variances matter, and the conversation |
| Competitor watch | Scans launches, pricing, hiring and funding news weekly, with links | What it means for your strategy |
| Long documents | Summarizes contracts, reports and research, and finds the clauses you asked about | Legal judgment and anything you sign |
| Meeting preparation | Briefs you on a company, a market or the last six months of a relationship | The relationship |
| All-hands and memos | Drafts and tightens messages for different audiences | Your voice, and what you choose to say |
| Customer feedback | Groups hundreds of comments into themes with quotes | Which themes to act on |
| Strategy work | Runs a pre-mortem, red-teams a plan, lists assumptions to test | The bet |
Models are weakest exactly where a CEO is exposed. They produce plausible numbers that are not in your data, cite sources that do not say what they claim, know little about anything recent unless they search, and tend to agree with however you framed the question. They also cannot be accountable. Use them to prepare and to challenge; never let them decide, send or sign.
Start in 15 minutes#
These work in Claude, ChatGPT, Microsoft Copilot or Gemini. Use your company's business or enterprise workspace for anything confidential, never a personal account.
Prompt
One-page decision brief from your documents
Using only the attached documents, write a one-page decision brief on: [DECISION, FOR EXAMPLE WHETHER TO OPEN A SECOND OFFICE IN LAGOS NEXT YEAR]. Sections: the decision in one sentence; three options including doing nothing; for each option the evidence for and against, citing the document and page; a recommendation; what would change the recommendation; and five questions I should ask my team before deciding. If the documents do not support a point, write "not in the documents" instead of filling the gap.
Good output cites a document for every claim and says "not in the documents" at least once. Open three of the citations; if one does not say what the brief claims, distrust the rest until you have checked them.
Prompt
Investor update first draft
Draft this month's investor update from the KPI table and notes below. Use only these numbers; after each number, write in brackets where it came from. Mark any number you calculated with the formula. Sections: three-line summary, KPI table (actual, plan, last month), highlights, lowlights with what we are doing about them, and specific asks. [PASTE KPI TABLE AND YOUR NOTES]
Good output has a bracketed source after every number. Tick each one against your table, and have finance confirm the closed numbers before anything goes out.
Prompt
Red-team my plan
Here is my plan: [PLAN]. Argue against it as the most skeptical member of my board. Give the three strongest objections, the evidence that would settle each one, and the one assumption that, if wrong, sinks the plan.
Good output names specific assumptions rather than generic risks. Use it to prepare for the real board meeting, not to replace it.
The tools CEOs use#
- Claude: Projects keep your documents and standing instructions together. Research, on paid plans, searches the web and your connected Gmail, Calendar and Drive, and writes a cited report. Scheduled tasks run on all paid plans and keep running when your computer is off. Connectors reach Google Drive, Gmail (read-only), Microsoft 365, and Slack on Team and Enterprise plans.
- ChatGPT: Projects, scheduled tasks, deep research, and ChatGPT Work for longer tasks that produce documents and decks. Business and Enterprise workspaces do not train on your data by default.
- Microsoft Copilot (renamed from Microsoft 365 Copilot): the Researcher agent writes cited reports across the web and your email, files, meetings and chats, up to 25 queries per user per month, and scheduled prompts run up to 10 recurring prompts. Both need a Copilot licence.
- Google Gemini: Deep Research across the web, Gmail and Drive; scheduled actions, up to 10 at a time; and Gemini Notebook, formerly NotebookLM, for questions across a fixed set of sources. Gems are being converted into skills from November 2026.
Pick the one your company already licenses. The habits matter more than the tool.
Workflow: the board and investor update
Members only below this line
Get the full CEOs and founders playbook free
What you get on this page:
- 4 step-by-step workflows
- 11 prompts
- 1 skill
- 1 hook
- 2 routines
Also in the members part
- Workflow: a decision brief from a reading pack
- Workflow: the weekly business review
- Workflow: a company AI policy and adoption cadence
- A skill for CEOs
- Guardrails and hooks
- Routines that run without you
- Prompt ladder for CEOs
- Measure it
- Risks and what not to delegate
Sources
Checked against these on 13 Oct 2026.
- Claude: what are projects (opens in a new tab)support.claude.com
- Claude: using Research (opens in a new tab)support.claude.com
- Claude: schedule recurring tasks (opens in a new tab)support.claude.com
- Claude skills: how to (opens in a new tab)claude.com
- Is my data used for model training? (Anthropic commercial products) (opens in a new tab)privacy.claude.com
- Microsoft Copilot: Researcher agent (opens in a new tab)learn.microsoft.com
- Microsoft Copilot: scheduled prompts (opens in a new tab)support.microsoft.com
- Microsoft Copilot: enterprise data protection (opens in a new tab)learn.microsoft.com
- Gemini: scheduled actions (opens in a new tab)support.google.com
- Gemini: Deep Research (opens in a new tab)support.google.com
- Claude Code hooks reference (opens in a new tab)code.claude.com
- EU AI Act implementation timeline (AI Act Service Desk) (opens in a new tab)ai-act-service-desk.ec.europa.eu
- EU AI Act Article 4: AI literacy (as amended) (opens in a new tab)ai-act-service-desk.ec.europa.eu
- UK government AI Playbook (opens in a new tab)gov.uk
- NIST AI Risk Management Framework (opens in a new tab)nist.gov
- SEC charges two investment advisers with making false statements about their use of AI (opens in a new tab)sec.gov
- METR: early-2025 AI and experienced open-source developer productivity (opens in a new tab)metr.org
- DORA: 2025 State of AI-assisted Software Development (opens in a new tab)cloud.google.com
- Generative AI at work (Brynjolfsson, Li and Raymond, QJE 2025) (opens in a new tab)doi.org