01Prompt
Challenge My Thinking
Challenge every assumption I'm making. Where could I be wrong? What evidence would change your recommendation?
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Free Resource · My AI Playbook
The 25 Prompts I Use Every Week.
If I could only keep twenty-five AI prompts, these are the ones I'd save.
They consistently help me think more strategically, communicate more effectively, and become a better event leader.
By Sara Straw
Introduction
A working playbook — not a prompt dump.
These 25 prompts aren't clever tricks. They're the questions I return to when I'm building a strategy, preparing for leadership, or trying to see my work more clearly.
Copy them. Adapt them. Make them your own. Then use them with the model you already trust.
The Playbook
25 prompts, in the order I actually use them.
02Prompt
Think Like My CEO
Review this proposal as my CEO. What excites you? What concerns you? What questions would you ask before approving it?
03Prompt
Think Like My CFO
Review this investment strictly from a financial perspective. Where is the risk? What information is missing?
04Prompt
Should This Event Exist?
Ignore history. Ignore tradition. Based on today's business priorities, should this event exist at all?
05Prompt
Build the Business Case
Write an executive business case explaining why this event deserves investment over competing priorities.
06Prompt
Portfolio Review
Review my entire event portfolio and recommend what to invest in, improve, consolidate, or retire.
07Prompt
Customer Perspective
Evaluate this experience entirely from the customer's perspective.
08Prompt
Executive Perspective
Evaluate this experience entirely from an executive's perspective.
09Prompt
Find My Blind Spots
What am I not thinking about?
10Prompt
Worst-Case Scenario
Assume this event fails. Walk backward and identify the five most likely causes.
11Prompt
Executive Summary
Rewrite this into a one-page executive briefing.
12Prompt
Dashboard Review
What decisions should leadership make after reading this dashboard?
13Prompt
Budget Optimization
Reduce costs by 20% while protecting the experiences that create the most business value.
14Prompt
AI Opportunities
Which parts of this workflow should remain human, and which could be improved by AI?
15Prompt
Leadership Coach
Coach me like an executive mentor. Challenge my thinking instead of agreeing with me.
16Prompt
Experience Audit
Walk through this event minute by minute and identify every moment of friction.
17Prompt
Executive Meetings
Which customers deserve executive meetings, and why?
18Prompt
Competitive Review
Compare this strategy against best-in-class technology companies.
19Prompt
Lessons Learned
What should become standard practice after this event?
20Prompt
Annual Planning
Design next year's event portfolio from scratch based on current business priorities.
21Prompt
Meeting Preparation
What difficult questions should I expect leadership to ask?
22Prompt
Storytelling
Turn these metrics into a compelling executive story.
23Prompt
Organizational Intelligence
What knowledge should be preserved so future teams never have to relearn it?
24Prompt
Executive Reflection
Based on my recent work, what leadership habits should I improve?
25Prompt
The One Question
If you were personally accountable for this business outcome, what would you do differently than I'm planning today?
Want More?
Access the full library of 250+ prompts.
The AI Prompt Library expands this playbook across strategy, planning, reporting, communication, and leadership.
Explore the Prompt Library →The AI Mindset
The quality of AI's answers will always be limited by the quality of the questions you ask.
Most people use AI to get answers faster.
The best leaders use AI to ask better questions.
That's a profound difference.
Technology will continue to evolve. Models will improve. Features will change. Workflows will become more sophisticated.
But curiosity, critical thinking, empathy, judgment, and leadership will remain uniquely human.
Use AI to accelerate your work. Use your experience to guide your decisions. And never forget that the most valuable role you play isn't planning events — it's helping people and organizations make better decisions through the experiences you create.
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Frameworks and toolkits for intentional leaders.
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