Pre-Flight Checklist: Ask More Questions (Post #19 of 20)
Can you be more curious?
What’s at the edge of the world you’ve created with AI?
(Movie spoiler alert)
In the final scene of “The Truman Show,” Truman discovers that world built around him was never real. He finds the edge of his reality because he keeps questioning the pieces that don’t add up. He literally sails into a wall that he thought was the horizon. As he breaks through and touches the wall, he knows.
What I love about this revelation is that it validates what he knew inside all along. That he knew he was being emotionally manipulated, but couldn’t prove it. However, he had the courage to start asking questions and push until he got answers. He could have just stayed in his comfortable world, even though he sensed something wasn’t right. But he was curious enough to sail to the edge of his world to know for sure.
This isn’t about encouraging paranoia or rebellion. I want to encourage everyone to consider agency, curiosity, courage and a simple refusal to accept things that you don’t understand. That’s all.
Don’t fear AI. But don’t stop thinking. Don’t accept everything at face value. Ask more questions. Curiosity is how you reclaim the narrative of your own life.
Artificial Intelligence has already begun to blur the lines between fact and fiction. There are things it does extraordinarily well, and many things it does poorly. Most of all, it is not always right. It gets facts wrong on a regular basis. It’s up to the recipient of the information to ask questions, instead of believing the output as ground truth.
AI generates answers through mathematical patterns and training data you will never fully see. You simply can’t know the depth of that training, the quality of the data or the strength of the guardrails. And despite confident assurances from Big Tech, the information supply chain remains far too easy to corrupt.
So, what can you do?
Don’t panic. Fear of the unknown can be quite paralyzing, but avoiding AI entirely isn’t realistic unless you’re living off the grid. Instead, do the one thing that Truman did better than anyone.
Ask questions.
3-Step Framework: Ask Better Quesitons
Curiosity isn’t a luxury in the AI era. It’s a survival skill.
These three steps can help anyone get started, regardless of technical background, to stay informed and empowered.
Ask, “What problem is this actually solving?” Before using any AI tool, or supporting its rollout, ask:
What job is this tool supposed to do?
Does it solve a real problem, or does it just introduce more complexity? (Does it have to be automated or over-engineered?)
Is this solving something meaningful, and why?
Ask, “How does this impact people?”
Who benefits?
Who absorbs the unintended consequences?
Does this just shift a burden to a quieter group?
Does it include human judgement?
Ask, “What guardrails exist to protect me?”
Can I verify or challenge its answer?
What learning model is it using and how is it trained?
What kind of security is included?
Guardrails aren’t obstacles like many believe. They’re intended to provide insurance policies for the humans that are relying on these systems. AI is not neutral. It has a decisive ripple effect and your questions protect your customers.
Test Flight: The Truman Question Drill (10 minutes)
Try this with any AI tool that you already use (e.g. ChatGPT, Gemini, Coplot…)
Ask yourself five simple questions:
What version of reality is this tool showing me? Think about what it includes, and what it leaves out.
What potential emotional manipulation might be at play? Does it just tell me what I want to hear because of my responses?
Could this be a hallucination? Not just, is it wrong. But how might it be wrong?
What data is it using? If you can’t see the supply chain of information, treat the output as a draft. As a data point, not a verdict.
Is the answer a fact, or just one possible answer? Think of every answer as a suggestion. Cross-reference with multiple sources.
Mission Debrief
How did it go? Did asking questions provide clarity?
The point isn’t to be afraid or to never believe anything again. The point is to be curious and ask questions.
Every answer should be considered:
one data point
one possible recommendation
one opinion
For each answer:
Be curious about the pros/cons
Cross-check with another resource
Ask ChatGPT (or whatever source you used), “What would be an argument against doing this?”
AI is going to continue to evolve and grow embedded in tools built for scale, not transparency. This is why curiosity really matters.
If you do nothing else, don’t forget to think.
Sail to the edge of your world, touch the wall, and choose a world where you can think for yourself.
Be brave enough to keep asking questions.