The Executive's AI Playbook: 25+ Prompts for Sharper Decisions
Stop Drowning in Data: The Executive's AI Playbook (25+ Prompts)
An executive's most valuable asset isn't capital; it's clarity and time. In a world of endless data streams, stakeholder demands, and constant market shifts, the primary job is to cut through the noise and make high-stakes decisions. This is where AI becomes a strategic lever, not just a tool.
Generative AI like ChatGPT can help you accelerate analysis, generate executive-ready summaries, and brainstorm strategic plans, allowing you to move faster and make sharper decisions. This post curates a powerful set of prompts, originally shared by OpenAI, designed to integrate AI directly into your leadership workflow.
Phase 1: Investor & Market Intelligence
Get critical insights faster. Instead of waiting for a full analyst report, use AI to survey market sentiment, benchmark performance against peers, or get a high-level overview of M&A opportunities in a new sector.
Prompts for Market Intelligence:
# Summarize investor trends
I’m preparing for our investor update. Research the latest funding and market trends in [industry]. Focus on valuation benchmarks, risk sentiment, and notable exits. Present in a concise brief with sources.
# Survey investor sentiment
Research current investor sentiment for companies in the [industry] space. Pull insights from earnings calls, investor letters, and analyst notes. Focus on risk appetite, funding trends, and growth expectations. Provide a 1-page briefing with source links.
# Evaluate M&A opportunities in a sector
I’m evaluating M&A options in the [sector/vertical]. Research recent acquisitions (past 24 months), typical deal sizes, common targets, and integration outcomes. Provide company examples, risks, and strategic rationale.
# Assess future trends in [your industry]
I’m an executive at [company/industry]. Conduct deep research on 3–5 emerging trends in [industry/topic] over the next 3 years. Include industry-specific examples, expert citations, and potential implications for strategy and talent planning.
Phase 2: Executive & Organizational Communications
Your most important job is setting the vision. AI helps you draft, test, and refine your message to ensure it's inspiring and clear. Use it to prep for town halls, design internal comms plans, or outline a new vision statement, ensuring total team alignment.
Prompts for Communication:
# Draft a vision statement
Help me draft a compelling vision statement for our [company/team/initiative]. Our focus areas are: [insert key goals, values, or direction]. Make it inspiring, concise, and easy to communicate across departments.
# Generate town hall talking points
I need talking points for an upcoming company-wide town hall. The theme is [insert theme or announcement]. Make it engaging, clear, and forward-looking. Limit to 5 minutes of content.
# Plan a reorg comms sequence
I’m planning communications for a reorg. Provide a step-by-step message plan by audience type (execs, managers, all staff). Include tone guidelines and delivery format per message.
# Draft a succession planning memo
Help me draft a succession planning memo for our [leadership team/board]. Include reasoning, timing, and a transparent outline of next steps for internal comms.
Phase 3: Strategic Planning & Decision Support
This is where AI acts as a true sparring partner. Move faster from idea to strategy. Model different pricing strategies, analyze market entry risks, or design a high-level 3-year plan based on your core business priorities.
Prompts for Strategy:
# Create a pricing strategy brief
We’re revisiting our pricing strategy for [product/service]. Based on [insert context: goals, customer segments, competitive positioning], suggest 2–3 pricing models and pros/cons of each.
# Prioritize growth levers
Given our goals [insert business goals], identify 3 high-potential growth levers and estimate effort vs. impact. Include a table with short descriptions and trade-offs.
# Analyze market entry risks
We are considering entering [new market/region]. Based on current economic, legal, and competitive factors, summarize key risks and mitigation strategies in bullet format.
# Design a 3-year strategy outline
Based on these business priorities [insert high-level goals], help me develop a high-level 3-year strategy. Include major focus areas, risks, and milestones per year.
Phase 4: Analytical Performance & Data Insights
Stop relying on static reports. Upload your raw datasets (CSVs, spreadsheets) and ask AI to be your on-demand data analyst. Have it identify top performers, analyze customer drop-off points, or forecast next quarter's KPIs based on historical trends.
Prompts for Data Analysis:
# Identify top and bottom performing segments
This is a dataset of performance across [regions/products/customers]. Identify which segments are over- and under-performing relative to the average. Show the metrics driving this and recommend 2 actions.
# Analyze quarterly business metrics
I’m reviewing performance data for Q[insert quarter]. Analyze this dataset [upload CSV] for key trends in revenue, churn, and customer acquisition. Highlight 3 insights I should share with the board.
# Analyze customer journey drop-off
I uploaded a funnel dataset showing customer journey stages. Analyze conversion rates between each stage and identify the largest drop-offs. Suggest 2–3 hypotheses and next steps to test.
# Forecast next quarter based on historical trends
Based on this historical data [upload], build a simple forecast for [KPI, e.g. revenue] over the next quarter. Use a basic time-series model and explain any assumptions made.
Phase 5: Executive Visualization & Framework Design
A good leader tells a clear story. Use AI to instantly create visual frameworks that simplify complex ideas for your board or team. Generate 2x2 matrices, competitive landscapes, or strategic flywheels to make your vision tangible and easy to understand.
Prompts for Visualization:
# Build a competitive landscape grid
Based on the following list of competitors and their differentiators [paste], create a 2x2 matrix plotting them by [x axis] and [y axis]. Label each quadrant and include our position.
# Design a 2x2 market positioning matrix
Create a 2x2 matrix plotting companies in [industry] by [X-axis: e.g. pricing] and [Y-axis: e.g. innovation]. Label each quadrant, add 6–8 companies, and highlight where we fit.
# Show transformation timeline
Create a visual timeline showing a company transformation journey from [year 1] to [year 3]. Include key milestones: strategy shifts, team growth, market expansion. Style: simple, bold, professional.
# Visualize strategic vision or flywheel
Create a high-level strategic flywheel or vision diagram for a company focused on [industry or goal]. Show how inputs (e.g. customers, data, feedback) loop into outputs (e.g. growth, innovation).
Your Turn: Put Them to Work
The best strategy is one that's executed. Start by picking one or two prompts from this list and integrate them into your workflow this week. The goal isn't to replace your judgment, but to give it superpowers.
How are you using AI in your leadership role? Share your most effective executive prompt in the comments below!
References & Further Reading
This collection is curated from OpenAI's official resources. To explore prompts for more than 20 other professions, visit the link below:
