There's a book called "how to decide" by Annie Duke that has some good advice on how to inspire this type of thinking.

For example, one of the ideas is the "doctor evil" or "imposter" game.

(1) Imagine a positive goal.

(2) Imagine that Dr. Evil has control of your brain, causing you to make decisions that will guarantee failure.

(3) Any given instance of that type of decision must have a good enough rationale that it won’t be noticed by you or others examining that decision.

(4) Write down those decisions.

Someone elses notes from this book: https://wisdomfromexperts.com/why-you-must-use-negative-thin...