Pre-Flight Checklist: Test Assumptions (Post #2 of 20)
What Would Have to Be True?
Isolated success can’t scale. Build the AI adoption framework first.
More than once, I have been with teams that were selling something we hadn’t built and building something we couldn’t sell.
A root cause of failure for many AI adoption launches isn’t technical, it’s strategic. Leaders get caught between the paralyzing fear of not having all the data, and the reckless impulse to launch with no plan or testing because they’re in a hurry and don’t want to be slowed down by process. It’s tough to stop the creative momentum. How do you help your teams balance “let’s get this to market” with “can we sell it?”
Your goal is to navigate this gap by turning assumptions into a something the teams can test, ensuring a strategic foundation for both adoption and engagement.
You have the vision, the mission and the problem defined. But 100% data certainty is elusive. At this critical decision point, an assumption isn’t a guess, it’s a strategic placeholder for missing data, allowing your mission to continue. Some may even call it, “a leap of faith.”
Assumptions are strategic tools that build a bridge between vision and execution.
In Post#1, you aligned your team on “What is the problem we are trying to solve?” Before you start writing code or buying tools, define what the conditions are for success.
Remember the ultimate question.
What would have to be true to succeed?
The answer defines your foundational framework.
In the movie clip above, Indiana Jones has this moment in The Last Crusade where he has to cross a bottomless chasm. From where he’s standing, it looks impossible. The only way forward is to take a leap of faith.
Now, here’s the thing: Indy doesn’t know there’s a bridge there. He assumes there must be. The question is: What would have to be true for that assumption to hold?
3 Steps for Testing Assumptions
Identify assumptions to test hypotheses.
Identify your top 3-5 assumptions (core beliefs).
Prioritize testing: Risk vs Effort
Align on the Go/No-Go Criteria
Test Flight - The Assumptions Grid Drill
Practice the strategic prioritization of assumptions.
Identify. Write your top three to five Go/No-Go core beliefs on separate sticky notes. These are your Go/No-Go Assumptions.
Prioritize. You can’t test every assumption at once. Prioritize the tests that offer the higher strategic reward for the lowest testing effort. This prevents spending weeks or months on tests that yield little insight or ROI.
Create a simple two-by-two grid on the whiteboard labeled: Y-axis: Impact of Failure (Low to High) and X-axis: Effort to Test (Low to High)
Label each assumption on a sticky note based on two criteria: Impact of Failure (Low or High) and Effort to Test (Low or High).
Priority 1: Low-Effort/High-Impact (“Low hanging fruit”). Test these first. They give you high confidence data for minimal cost.
Priority 2: High Effort/High-Impact (These are your most critical strategic bets. Dedicate resources only after Priority 1 is complete.)
Align. Risk mitigation means have a strategic plan to pivot safely if your assumptions are wrong. You must decided before you launch what failure looks like.
For each core assumption, define the Go/No-Go criteria. If the data falls below your success threshold, then you stop the test and pivot to the next one. This eliminates emotional debates and ensures controlled failure.
Place each sticky note on the grid you created.
Reflect. Examine the Low-Effort/High-Impact Quadrant. This is your immediate Priority 1 testing queue. If that quadrant is empty, your assumptions are fundamentally too risky and lacks easy wins.
Mission Debrief
How did it go? Do you have prioritized assumptions to test?
This exercise is meant to demonstrate a sample of the essential conditions for success, and completing it with your team will allow you to build a foundation that can be continuously challenged and validated.
In the next post, we’ll dive into the biggest risk your assumptions will need to mitigate: defining and eliminating Shadow AI, the unmanaged tools that threaten your entire foundation.
(This clip from Indian Jones and the Last Crusade demonstrates how to test an assumption. Just in case the Holy Grail is what you seek.)