Strategic Planning with AI: How to Build Your Virtual Advisory Board
By Jason Halberstadt, CEO MyTrip.AI
In today’s fast-moving travel industry, relying on gut instinct alone can leave you scrambling when unexpected crises hit. What if you could convene the world’s top minds—right at your keyboard—to help you think through every scenario? With the right AI prompts, you can.
Listen to the Podcast on Spotify.
Why AI-Driven Strategy Matters for Travel Leaders
As travel operators, we all carry our personal biases and past experiences into decision-making. That can mean repeating last year’s best-selling tour or tweaking what didn’t quite sell—without ever asking whether a radically new approach might be better. AI can:
Remove reactive habits: Shift from “what worked before” to “what could work next.”
Offer diverse perspectives: Simulate insights from industry legends, political analysts, even military experts.
Speed up research: Generate data-driven projections in minutes, not weeks.
Introducing the CRIT Framework
To get the most from AI, Jason Halberstadt recommends a simple prompting acronym—C.R.I.T.—that mirrors how you’d onboard any new team member:
C: Context
Define the situation clearly.
Example: “A regional conflict has closed Dubai’s airports. We’re Adventure Dubai Inc., a skydiving tour operator. We must forecast visitor volumes over the next 12 months.”
R: Role
Assign your AI “advisor” a persona with deep domain expertise.
Example: “You are the CEO of Emirates Airlines, expert in aviation and tourism trends.”
I: Interview
Invite clarifying questions before analysis—just like a human consultant.
Example: “Please ask any questions you need about our historical passenger data, customer segments, or cost structure.”
T: Task
Specify the deliverable.
Example: “Create a month-by-month tourism forecast for Dubai’s top markets: UK, India, Saudi Arabia, Russia, US, and Israel.”
A Real-World Role-Play: Navigating a Crisis in Dubai
In the podcast, Jason and host Jason Elkins ran a live demo:
Set the scene: War has broken out; airports are closed.
Assemble your dream team:
Aviation expert (Emirates CEO) to forecast passenger volumes.
Political analyst to project conflict timelines.
Military advisor to assess airspace reopening.
Run CRIT in one thread: Keep the session alive so each persona’s input builds on the last.
Elevate to your strongest model: At the end, ask your most capable AI (e.g., GPT-4) to synthesize all perspectives into a unified strategic plan.
This “fantasy football” of advisory boards delivers rapid, multi-angle insights—helping you anticipate staffing needs, marketing pivots, and operational contingencies.
Tips for Getting Quality AI Advice
Be honest: If you don’t know your exact marketing spend, tell the AI—it will recommend one.
Encourage questions: Grant your virtual advisor “permission” to clarify unknowns.
Think critically: Treat AI recommendations like you would any expert—they’re inputs, not gospel.
Next Steps: Diagnose Your Top Challenges
If you’re still defining your strategic priorities, check out our blog post on the 50 Largest Challenges Facing Travel Companies in 2025. It’s like a menu of the biggest pain points—pick one or two to frame your next AI-powered advisory session.
Then, fire up your favorite AI tool and apply the CRIT framework to your own most pressing problem. You’ll walk away with fresh perspectives, data-driven forecasts, and the confidence to make proactive decisions for whatever comes next.
Ready to build your AI advisory board? Share your experiences in the comments below!