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What Are the Best AI Prompts for CEOs? 12 to Copy and Use

Twelve prompts that turn ChatGPT, Claude or Copilot into a sparring partner for strategy, boards, investors and your people, written for UK CEOs and MDs.

By Harry LangPublished 9 November 202611 minute read

The Chairman's Engine > best prompt for... ask the hard question first The Chairman's Engine Fig. 2
In this article
  1. What makes a good AI prompt for a CEO?
  2. What are the best ChatGPT prompts for CEOs on strategy and decisions?
  3. Which AI prompts help a CEO prepare for the board and investors?
  4. What are the best AI prompts for CEOs leading their people?
  5. How can a CEO use AI as a chief of staff?
  6. Which AI tool should a CEO use: ChatGPT, Claude, Copilot or Gemini?
  7. How do you get your leadership team using AI prompts well?
  8. AI prompts for CEOs: questions people ask

The short answer

The best AI prompts for CEOs make the AI challenge you, not flatter you. Use prompts that draft strategy memos from rough notes, run decision pre-mortems, rehearse board questions, write candid investor updates, prepare all-hands talks and run a weekly chief of staff review, always with your context, a clear output and approved tools.

The best AI prompts for CEOs do the work a good chief of staff would: sharpen your thinking, challenge your decisions and turn rough notes into papers people can act on. Here are 12 I give managing directors and founders, ready to use in ChatGPT, Claude, Microsoft Copilot or Gemini.

Most CEOs I train start by using AI to write emails faster. That is fine, but it is the least valuable thing it can do for you. The real gains come from using it as a sparring partner on strategy, boards and people, the parts of the job where nobody else in the business can tell you you are wrong. This page is part two of a series that starts with the best AI prompts for business.

What makes a good AI prompt for a CEO?

A good CEO prompt gives the AI your context, asks it to challenge you rather than flatter you, and demands a specific output you can use in the next meeting. AI tools are built to be agreeable, so you have to ask for disagreement explicitly.

The lazy version
What do you think of my plan to expand?

Why it falls flat: No plan, no context, and an open invitation to be polite.

The better version
Act as a sceptical investor. Here is my plan to open a second site: [paste summary]. Our current position: [revenue band, margin, headcount, cash]. Give me the three weakest assumptions, what evidence would test each one, and the question you would ask me in a board meeting that I would least like to answer. Do not soften it.

Why this prompt works

It sets a role, supplies context and asks for challenge, not praise.

If you want a wider method for building prompts like this, my page on AI prompt frameworks sets out the structures I teach.

What are the best ChatGPT prompts for CEOs on strategy and decisions?

The best ChatGPT prompts for CEOs on strategy turn your thinking into a clear written argument, then attack it. For a full planning toolkit, see AI prompts for business strategy.

Draft a strategy memo from rough notes

Prompt 1
You are a strategy adviser to the CEO of a UK [sector] business with [headcount] staff. Using my notes below, draft a two-page memo to the leadership team on [topic]. Structure: the situation in three sentences, the choice we face, at least three options including doing nothing, my recommendation and why, what we stop doing as a result, and how we will know in six months if it is working. Plain British English. Mark where my notes are thin and I need evidence.

Notes:
[paste]

Why this prompt works

"What we stop doing" forces a real choice.

Run a decision pre-mortem

Prompt 2
We are about to [decision, e.g. open a second site in Bristol]. Here is the business case: [paste summary]. Imagine it is two years later and this decision has clearly been a mistake. Tell the story of how it went wrong, then pull out the five root causes. For each, give a leading indicator we could track monthly and a cheap test we could run before committing. Be blunt; I do not need reassurance.

Why this prompt works

Cheap tests turn worry into action.

Make the case for the option you are rejecting

Prompt 3
I am leaning towards [option A] over [option B] for [decision]. My reasoning: [paste]. Make the strongest honest case for option B, as its best advocate on my board would. Then show where my reasoning rests on untested assumptions and what evidence would change the answer either way. Finally, tell me whether this decision is reversible and how much time it deserves as a result.

Why this prompt works

It protects you from your own confirmation bias.

Scan competitors from public material

Prompt 4
Here is material on [number] competitors: website copy, pricing pages, job adverts and press releases [paste]. Build a table comparing them on target customer, main message, price position, recent moves and hiring focus. Then tell me what their job adverts suggest about where they are heading. Use only the material provided and label anything inferred as "inference". End with three questions this raises for our strategy.

Why this prompt works

Job adverts reveal plans that websites do not.

Which AI prompts help a CEO prepare for the board and investors?

AI prompts help most with board and investor work when they make the AI play your audience, so you hear the hard questions before the meeting. Your board members may want the best AI prompts for directors for their side of the table.

Rehearse the board's questions

Prompt 5
I am presenting this paper to our board next week: [paste paper]. The board includes [describe members, e.g. a finance-minded chair, an investor director, an operations NED]. For each member, list the three questions they are most likely to ask and the weak points they will spot. Then suggest what to add or cut so the paper answers those questions before they are asked, keeping it the same length or shorter.

Why this prompt works

Playing each board member makes the rehearsal specific.

Write an honest investor or stakeholder update

Prompt 6
Write our quarterly update to [investors, shareholders or our bank]. Facts for this quarter: [paste key numbers, wins, misses and next priorities]. Structure: one-sentence headline, numbers against plan, what went well, what did not and what we are doing about it, our asks, and the outlook. Be candid about misses. Under 400 words. Do not add any figure I have not given you.

Why this prompt works

Banning new figures keeps the numbers yours.

Get through a long report in ten minutes

Prompt 7
I will paste a [consultant's report, market study or audit]. I have ten minutes. Give me the bottom line in one paragraph, the five findings that matter for a business like ours ([describe size and sector]), anything that contradicts what we currently believe, the recommendations ranked by effort and impact, and section references so I can check the originals. Flag any claim that relies on a source the report does not name.

[paste report]

Why this prompt works

Section references let you verify before you quote.

What are the best AI prompts for CEOs leading their people?

The best AI prompts for leading people help you say hard things clearly and anticipate how they will land. They do not replace the conversation itself.

Prepare an all-hands talk

Prompt 8
Draft talking points for a ten-minute all-hands on [topics]. Our people are [describe, e.g. 60 staff across office and warehouse, some anxious about change]. Give me an honest opening about where we are, three messages with one real example each, what is changing for them and what is not, and a close that tells them what happens next. Write it to be spoken: short sentences, no slide language. Then list five questions staff might ask, with straight answers.

Why this prompt works

Spoken language lands better than a read-out memo.

Prepare for a difficult announcement

Prompt 9
I need to announce [change, e.g. a restructure of the customer service team]. Here are the facts and what has been decided: [paste, no names]. List the twelve hardest questions staff, managers and customers might ask. Draft an honest answer to each, and mark any I cannot answer yet or where I must take HR or legal advice first. Tell me which questions to answer up front in the announcement itself.

Why this prompt works

It shows you where you need advice before you speak.

Write a delegation brief for an executive

Prompt 10
I want to hand [project] to [role, e.g. our operations director]. Here is what I know: [paste]. Write a one-page delegation brief: the outcome I want, why it matters, decisions they can make without me, decisions they must bring back, budget and deadline, who else is involved, and when we will check in. Then tell me which parts of my notes suggest I am still holding on too tightly.

Why this prompt works

The last line catches the CEO who cannot let go.

Your managers will need their own versions of these; AI prompts for managers covers 1:1s, feedback and reviews.

How can a CEO use AI as a chief of staff?

A CEO can use AI as a chief of staff by giving it a weekly dump of notes and priorities and asking it to hold you to account. Two prompts do most of the work.

Run a Friday chief of staff review

Prompt 11
Act as my chief of staff. Below are my notes from this week: meetings, flagged emails, pending decisions and how I think things are going [paste]. Our priorities this quarter are [list]. Give me a Friday review: what moved forward, what stalled and why, decisions I am sitting on, people I need to speak to, and the three things that deserve my best hours next week. Be direct if my time does not match the priorities.

Why this prompt works

Weekly repetition turns it into a habit, not a novelty.

Make it better

In Claude or ChatGPT, save your priorities and context in a project so you only paste the week's notes. In Microsoft Copilot, it can draw on your Outlook and Teams activity directly, if your organisation has enabled it.

Audit your calendar against your priorities

Prompt 12
Here is my calendar for the last two weeks as a list of meeting titles and durations [paste, external names removed]. My priorities are [list]. Sort my time into strategy, people, customers, operations, admin and could be someone else's. Show the hours in a table against what a CEO focused on these priorities should spend. Suggest five meetings to cut, shorten or delegate, and one recurring block to protect.

Why this prompt works

Your calendar shows your real strategy.

Which AI tool should a CEO use: ChatGPT, Claude, Copilot or Gemini?

A CEO should use whichever tool the business has approved, with the right data controls, and pick the strongest one for the task. These prompts work in all four. I compare two of them in detail in ChatGPT vs Copilot for business.

AI tools for CEOs compared
ToolBest CEO useWatch for
ChatGPTThinking out loud, drafting memos and talksUse a business plan, not a personal account
ClaudeLong reports, careful writing, board papersApproved accounts only for confidential papers
Microsoft CopilotWeekly reviews from your own Outlook, Teams and filesIt sees what you can see, so permissions matter
GeminiFirms running on Google WorkspaceCheck which Workspace data it can reach

How do you get your leadership team using AI prompts well?

You get a leadership team using AI well by agreeing the rules, practising on real work together and building a shared prompt library. Sending round a list of prompts, this one included, will not do it on its own.

  1. Set the rules firstAgree which tools are approved and what must never be pasted in. How to write an AI policy shows how.
  2. Practise on a live problemTake a real decision your team faces and run the pre-mortem and steelman prompts on it together.
  3. Share what worksKeep a short library of prompts your leaders actually reuse, with an owner.
  4. Tie it to strategyLink AI use to your plan; how to write an AI strategy covers this.
  5. Train the next layerYour managers copy your habits. Make sure the habits are good ones.

In my experience, leadership teams change their habits when they see AI work on their own papers, in the room, with someone answering the awkward questions. That is what my Claude & ChatGPT Prompts, Context & Skills Deep Dive is for. If you want to see where your team stands first, take the free AI Capability Assessment.

AI prompts for CEOs: questions people ask

What are the best AI prompts for CEOs?

The most useful are prompts that challenge your thinking: decision pre-mortems, making the case for the option you are rejecting and rehearsing board questions. Add prompts for strategy memos, investor updates, all-hands talks and a weekly chief of staff review, and you cover most of the job.

Should a CEO use ChatGPT, Claude or Copilot?

Use the tool your business has approved with proper data controls. Claude is strong on long documents, ChatGPT on drafting and thinking aloud, and Copilot on work inside your own Microsoft 365 emails and files.

Can I put board papers into ChatGPT?

Only into an approved business account with suitable data controls, and only if your policy allows it. Never use a personal account for confidential board, deal or staff information. If in doubt, summarise or anonymise first.

How do I stop AI just agreeing with me?

Ask for disagreement explicitly. Give it a sceptical role such as an investor or NED, ask for the weakest assumptions and tell it not to soften the answer. Then judge the output yourself; it is a sparring partner, not an adviser.

How much time should a CEO spend learning AI?

Enough to use it well on your own work and to set the example for your team. A focused session on your real papers usually teaches more than weeks of trial and error. My AI strategy workshop for business leaders is built for exactly that.

How do I get my leadership team using AI?

Agree the rules, practise together on a live decision and keep a shared library of prompts that work. Leaders copy each other, so training the leadership team together tends to spread good habits faster than individual experimenting.

Keep reading

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Get your leadership team prompting properly

I train UK leadership teams in person and online to use ChatGPT, Claude and Copilot on their own strategy, board and people work, with a clear policy and habits that spread to the rest of the business.

Harry Lang
Harry Lang founded The Oxford AI School in Witney, Oxfordshire. He trains UK businesses and teams to use AI well, writes the Marketing Unfiltered newsletter, and is the author of Learn To Fly With AI.