AI for executives: briefings, drafts and better questions

Senior leaders do not have time to become AI experts, and they do not need to. What matters is a short list of uses that reliably return time, and a clear sense of where the tools mislead.

Where AI helps executives

Compressing reading. Long reports, contracts, long email threads and background documents can be summarized into what matters: decisions required, risks, dates and open questions. Ask for citations to the location in the source so you can spot-check the parts that drive a decision.

Drafting in your voice. Board updates, all-hands notes, investor letters and difficult emails all start as a blank page. Give the assistant your rough notes and a sample of your writing, and it produces a first draft. The improvement comes from prompting well, covered in how to write better AI prompts.

Preparing for meetings. Feed it the last meeting’s notes, the relevant documents and your goal, and ask for a one-page brief and the five questions you should ask. Also use it against yourself: paste your plan and ask for the strongest objections.

Regular reporting. If a report is built the same way every week, it can be automated so it lands in your inbox already summarized. The weekly reports question explains the pattern.

Research. Tools such as Perplexity and Claude can produce a sourced competitive or market brief quickly. Read the sources it cites rather than trusting the summary.

Where AI does not help

• Decisions. It can widen the options you consider. It does not know your context, incentives or politics.
• Facts you have not verified. A hallucination reads exactly like a correct statement. Anything you will repeat externally needs a source.
• Sensitive judgment calls about people. Do not use it to decide on performance, compensation or discipline.

Risks specific to leaders

Confidential information. Board materials, M&A, unreleased financials and personnel matters carry legal and competitive risk. Consumer chat tools and company-managed tools differ in data handling. Before you use any tool with sensitive material, confirm the terms, and see is it safe to put company data in ChatGPT.

Setting the tone. If you use AI quietly and your team has no rules, people will improvise. A company AI policy does not need to be long, but it should exist.

Over-trusting a polished summary. A well-written summary feels finished. Ask what it left out.

Tool choice. There are several credible options. Which AI tool to use at work is a better starting point than following whatever your team bought first.

Starter prompts

Meeting brief:

I have a meeting with [person/team] about [topic]. Using the
notes and documents below, write a one-page brief: the situation,
what they probably want, what I want, three risks, and five
questions I should ask. Mark anything you are inferring rather
than reading from the documents.

Stress-test:

Here is my plan. Play the most skeptical member of my board.
List the five strongest objections, ranked by how damaging
each would be, and what evidence would answer each.

Your first week

• Day 1: Choose one tool and confirm its data terms with whoever handles IT or legal.
• Day 2: Summarize one long document you already know well. Test the summary against your own understanding.
• Day 3: Use the meeting brief prompt for two upcoming meetings.
• Day 4: Draft one update from your own notes and compare it to your usual version.
• Day 5: Pick the report you read most often and ask your team who could automate it.

A worked example: the board pre-read

You have a 60-page board deck and a stack of supporting memos, and two hours. If the material is cleared for use with your chosen tool, ask for the ten things a board member is most likely to question, with the page reference for each. Ask which numbers changed materially from last quarter and where the deck is inconsistent with itself. Then ask for a two-page summary in your voice for your own preparation.

You read the flagged pages, not the whole deck. The summary is a map, and you use the original for anything you plan to say aloud. If the material is not cleared for use, do this exercise on last year’s public materials until it is.

Common mistakes to avoid

• Using a personal account for company material. Consumer and business terms differ.
• Forwarding an AI summary without reading the source. The error will carry your name.
• Asking for advice with no context. The output improves sharply when you explain constraints and goals.
• Delegating tool rules to whoever complains first. Set them once.

What the sources say

Occupational data for top executives, the World Economic Forum on employer expectations, and NIST on generative AI risk.

• The Bureau of Labor Statistics projects overall employment of top executives to grow 5 percent from 2025 to 2035, faster than the average for all occupations.
• The Bureau of Labor Statistics says chief executives will be needed in organizations to govern and make high-level decisions.
• In the World Economic Forum employer survey, 86% of employers expect AI and information processing technologies to be transformative by 2030.
• The National Institute of Standards and Technology defines confabulation as the production of confidently stated but erroneous or false content, and lists it as a generative AI risk.

A faster way to build the habit

Learn AI Fast is a two-day in-person class in Boston for non-developer professionals. It covers the tools, a prompting framework, workflow design, data privacy and the basics of a workplace AI policy, using provided case files.

Sources

• U.S. Bureau of Labor Statistics, Occupational Outlook Handbook: Top Executives: “projected to grow 5 percent from 2025 to 2035, faster than the average for all occupations”
• U.S. Bureau of Labor Statistics, Occupational Outlook Handbook: Top Executives: “Chief executives will be needed in organizations to govern and make high-level decisions”
• World Economic Forum, The Future of Jobs Report 2025 (digest): “particularly AI and information processing (86%)”
• NIST, AI 600-1: Artificial Intelligence Risk Management Framework: Generative AI Profile: “erroneous or false content”