Lateral Thinking Starts with Challenging Assumptions
I recently completed the course The Art of Creative Disruption: Master Lateral Thinking in the Age of AI, and it forced me to rethink something we don’t talk about enough in business anymore: how to think creatively on purpose.
We brainstorm, we strategize, we “circle back”—but genuine idea-making has become a lost art. Lateral thinking, however, brings it back to life. Here are the biggest lessons I walked away with—and why they matter for anyone who wants to stay relevant, curious, and innovative in the AI era.
We tend to look at problems by staring harder in the same direction—hoping more effort will magically reveal a new solution. But as the course reminded me: you can’t see in a different direction by staring harder in the same one.
Lateral thinking forces you to turn your head. That means asking questions like:
What are we actually trying to achieve here?
Why do customers really buy our product or service?
Is there a better—or different—way to deliver this?
This isn’t about being clever. It’s about being willing to see the problem differently. Charles Darwin mastered this. His famous question— “Why are there so many different types of finches on the Galápagos Islands?”—seems obvious in hindsight. But it was a question no one else thought to ask. And it reshaped biology forever.
Ask All the Questions (Especially the “Dumb” Ones)
As a kid, I was painfully shy. Teachers said, “There are no dumb questions,” but I never believed them until adulthood.
Turns out, “dumb” questions are often the ones that crack problems open.
In fact, one person in the course shared a story about their child asking, “Daddy, what does a tickle look like?” That single question—sweet, strange, and utterly unexpected—became the seed for a book. Great questions don’t have to sound sophisticated. They need to be sincere, curious, and a little bit childlike.
Try asking:
What if the opposite were true?
What if we removed the most obvious part of this process?
What if no one had ever done it “this way” before?
These aren’t childish questions. They are bold ones.
Use Generative AI as Your Thinking Partner, Not a Shortcut
One of the most surprising takeaways from the course was how effectively generative AI can enhance lateral thinking when used intentionally.
Not to get answers—but to uncover assumptions.
For example: Let’s say sales are low. The default assumption might be: Our pricing must be competitive. Ask ChatGPT:
“What assumptions might we be making without realizing it?”
Suddenly, you get 10 possible angles you never considered. You can even “pretend you’re a consultant” and let AI pepper you with questions the way a strategist would. It pulls you out of your own mental rut and helps you see blind spots.
Random Words: A Playground for Creativity
Another technique that blew my mind is the Random Word method. The idea: take a challenge you’re facing, open a dictionary at a random noun, and force a connection between the word and your problem.
Sometimes it works brilliantly. Sometimes it fails. But when it works, the ideas are often radical and highly creative.
Here’s an example:
Problem: We can’t recruit enough engineers and programmers.
Random Word: Menu
Ideas sparked:
Offer a menu of benefits instead of a standard brochure—letting candidates pick perks that matter most to them.
Conduct interviews in a restaurant, breaking away from stiff office settings.
Host a weekly “menu” of takeaway food to showcase company culture.
Another variation: set challenges in recruitment ads—like puzzles, Sudoku, or coding competitions—to find candidates who love problem-solving.
The lesson? Creativity isn’t just about thinking harder—it’s about forcing your brain to make unexpected connections, even with seemingly unrelated words. Lateral thinking in action: sometimes quirky, sometimes brilliant, but always a way to break conventional patterns.
Turn and Face the Strain
David Bowie once said, “Turn and face the strain.” Lateral thinking asks us to do exactly that.
Instead of clinging to what we know—or staring harder at the same problem—we shift our perspective, even if it feels uncomfortable.
Especially if it feels uncomfortable.
In a world where AI can generate answers instantly, human value lies in the quality of our questions.
Creativity Thrives on Childlike Curiosity
Kids are natural lateral thinkers. They don’t know the rules yet—which makes them phenomenal at breaking them. Adults, on the other hand, want to look competent. Polished. Sophisticated. But sophistication rarely sparks innovation. Curiosity does.
The course encouraged us to stay childlike: ask more questions, simpler questions, even obvious questions. Especially the questions that feel too basic to say out loud. This is where truly original ideas come from.
Final Thought
If you’re feeling stuck, if your team is recycling the same ideas, or if you’re craving the energy of real brainstorming again, start asking different questions. Ask stranger questions. Ask braver questions.
AI isn’t replacing creative thinkers—it’s demanding that we become better ones.
And lateral thinking is how we get there.