AI for Commercial Leaders
25 AI Prompts for Commercial Leaders
25 practical AI prompts designed to help commercial leaders challenge their thinking, prepare for customers and negotiations, explore growth opportunities and make better decisions.
25 AI Prompts for Commercial Leaders
AI is changing the way commercial teams work. For commercial leaders, the more interesting opportunity is to use AI to challenge thinking, explore possibilities and improve decision-making. The quality of the output depends partly on the quality of the question. These AI prompts for commercial leaders are designed around the commercial challenges that matter most.
COMMERCIAL JUDGEMENT
1. Challenge my commercial strategy
Prompt: “Act as an experienced commercial strategist. Review the following commercial strategy and identify the five assumptions that are most critical to its success.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
2. Identify what we’re missing
Prompt: “Review the following commercial situation from the perspective of an experienced commercial leader. Identify the three most important factors we may be overlooking.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
3. Stress-test a recommendation
Prompt: “Here is my commercial recommendation. Build the strongest possible argument against it. Identify the assumptions, risks, unintended consequences and alternatives.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
4. Find the real commercial question
Prompt: “Review the following commercial problem. Strip away the symptoms and identify the underlying commercial question we actually need to answer.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
5. Prepare for a difficult decision
Prompt: “Help me prepare for this commercial decision. Identify the key options, likely benefits, risks, trade-offs and second-order consequences.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
CUSTOMER & ACCOUNT MANAGEMENT
6. Prepare for a customer meeting
Prompt: “Act as an experienced commercial strategist. Review the following commercial strategy and identify the five assumptions that are most critical to its success.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
7. Challenge my customer assumptions
Prompt: “Review the following commercial situation from the perspective of an experienced commercial leader. Identify the three most important factors we may be overlooking.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
8. Find opportunities to create customer value
Prompt: “Here is my commercial recommendation. Build the strongest possible argument against it. Identify the assumptions, risks, unintended consequences and alternatives.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
9. Improve an account plan
Prompt: “Review the following commercial problem. Strip away the symptoms and identify the underlying commercial question we actually need to answer.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
10. Generate better customer questions
Prompt: “Help me prepare for this commercial decision. Identify the key options, likely benefits, risks, trade-offs and second-order consequences.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
NEGOTIATION
11. Prepare for a negotiation
Prompt: “Act as an experienced commercial strategist. Review the following commercial strategy and identify the five assumptions that are most critical to its success.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
12. Understand where the value is
Prompt: “Review the following commercial situation from the perspective of an experienced commercial leader. Identify the three most important factors we may be overlooking.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
13. Challenge my negotiation position
Prompt: “Here is my commercial recommendation. Build the strongest possible argument against it. Identify the assumptions, risks, unintended consequences and alternatives.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
14. Identify potential trade-offs
Prompt: “Review the following commercial problem. Strip away the symptoms and identify the underlying commercial question we actually need to answer.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
15. Prepare for objections
Prompt: “Help me prepare for this commercial decision. Identify the key options, likely benefits, risks, trade-offs and second-order consequences.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
PRICING & REVENUE GROWTH
16. Diagnose revenue growth
Prompt: “Act as an experienced commercial strategist. Review the following commercial strategy and identify the five assumptions that are most critical to its success.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
17. Identify the highest-quality growth opportunity
Prompt: “Review the following commercial situation from the perspective of an experienced commercial leader. Identify the three most important factors we may be overlooking.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
18. Challenge a pricing strategy
Prompt: “Here is my commercial recommendation. Build the strongest possible argument against it. Identify the assumptions, risks, unintended consequences and alternatives.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
19. Find where growth could destroy value
Prompt: “Review the following commercial problem. Strip away the symptoms and identify the underlying commercial question we actually need to answer.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
20. Build a downside scenario
Prompt: “Help me prepare for this commercial decision. Identify the key options, likely benefits, risks, trade-offs and second-order consequences.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
STRATEGY & LEADERSHIP
21. Explore strategic options
Prompt: “Act as an experienced commercial strategist. Review the following commercial strategy and identify the five assumptions that are most critical to its success.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
22. Analyse a competitor
Prompt: “Review the following commercial situation from the perspective of an experienced commercial leader. Identify the three most important factors we may be overlooking.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
23. Prepare an executive recommendation
Prompt: “Here is my commercial recommendation. Build the strongest possible argument against it. Identify the assumptions, risks, unintended consequences and alternatives.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
24. Challenge my leadership approach
Prompt: “Review the following commercial problem. Strip away the symptoms and identify the underlying commercial question we actually need to answer.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
25. Prepare for a senior leadership meeting
Prompt: “Help me prepare for this commercial decision. Identify the key options, likely benefits, risks, trade-offs and second-order consequences.”
Why use it? Use this prompt to surface assumptions, strengthen preparation and bring more commercial judgement to the decision.
THE IMPORTANT BIT: CONTEXT MATTERS
The prompts above are deliberately structured, but the quality of the context you provide will materially influence the quality of the output. Include customer objectives, recent performance, relationship history, commercial terms, known challenges, priorities, constraints and relevant data.
USE AI AS A CHALLENGER, NOT THE DECISION-MAKER
AI can help commercial teams structure, analyse, challenge, explore, synthesise and prepare. The commercial leader still needs to judge, prioritise, decide and take accountability.
A SIMPLE COMMERCIAL AI WORKFLOW
THINK
01 FRAME
What are we actually trying to decide?
02 CONTEXT
Give AI the relevant information.
03 CHALLENGE
Expose assumptions, gaps and weaknesses.
04 EXPLORE
Ask it to generate options and scenarios.
05
DECIDE
Apply your own commercial judgement.
HUMAN COMMERCIAL JUDGEMENT
06 STRESS-TEST
Pressure-test the decision before acting.
07 ACT
Turn the decision into clear actions.
AI expands the thinking. You own the decision.
WANT THE PROMPTS IN ONE PLACE?
I’ve put together a free collection of practical AI prompts designed specifically for commercial leaders. Customer preparation. Negotiation. Strategy. Pricing and growth. Leadership. No generic productivity hacks — just practical ways to think better, prepare better and move faster.
FINAL THOUGHT
The most useful question for a commercial leader isn’t “How can I use AI?” It’s “Where could better thinking change the commercial outcome?” Start there.