PROMPT This AI Challenge
"The Strategy Handoff: Where Good Plans Go Off Track" featuring Brooks Busch
Every episode of the PROMPT This podcast includes an AI Challenge for the audience. Follow the instructions below to complete this episode's challenge.
Most leaders believe their teams are aligned because the leader feels clear. That belief is usually wrong. The most common failure in strategy is not bad intent or poor effort. It is the illusion of alignment. Everyone nods. Everyone agrees. Then execution drifts because each function heard a different priority.
This AI Challenge exposes those gaps fast.
Step 1: Write your one sentence priority
Pick the single most important initiative your team is driving this quarter. Write it in one sentence exactly as you would say it in a leadership meeting. No qualifiers. No sub bullets. This sentence is your baseline.
Examples across industries:
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Manufacturing: Reduce production lead times to improve on time delivery.
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Product company: Ship the new platform experience to drive adoption.
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Services firm: Increase client retention by standardizing delivery quality.
Step 2: Ask AI to translate it across roles
Now test how that sentence mutates when filtered through different mental models.
Use this prompt and paste in your sentence.
Rewrite this priority from the perspective of the CFO, the Head of Sales, a frontline individual contributor
Keep each version to one sentence.
AI will return three interpretations. None are wrong. All are revealing.
Step 3: Compare the interpretations
This is where the signal appears.
What typically shows up:
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CFO interpretation emphasizes cost, risk, margins, capital efficiency, or predictability.
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Head of Sales reframes around revenue, pipeline impact, customer proof, or urgency.
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Individual contributor turns it into a task list or local action they think they own.
These differences are not misunderstandings. They are perspective fingerprints. They show how your message is being reinterpreted the moment it leaves your mouth.
In manufacturing, this often exposes tension between throughput and cost control.
In product companies, it reveals confusion between shipping and adoption.
In services firms, it highlights the gap between growth goals and delivery reality.
Step 4: Tighten the original message
Rewrite your original one sentence priority using what you learned.
The goal is not to satisfy every function. The goal is to write a sentence that cannot be misinterpreted regardless of role.
This is the clarity discipline Brooks pushes leaders to build. Alignment is not agreement. Alignment is shared interpretation.
Why this challenge works
It forces leaders to confront a hard truth.
Your message is not what you say. Your message is what people hear.
In under five minutes, this exercise reveals:
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Where assumptions are hiding
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Where language is too vague
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Where functions will naturally drift
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Where alignment is fragile before execution starts
AI Prompts
Final Thought
Most execution failures are born in the sentence that kicks off the work. If that sentence means different things to different people, misalignment is guaranteed. This challenge gives leaders a fast, repeatable way to test clarity before confusion compounds. Five minutes of discipline here can save months of rework later.
