Category Archive

Better Questions

All published essays and notes on better questions and durable methodology.

Thinking Fast, Asking Better

How Daniel Kahneman's work provides a supporting lens for slowing down, exposing assumptions, and getting past AI's confident first answer.

Why speed is the enemy of diagnostic accuracy in complex client strategy.

Why defining "what must not happen" produces better system constraints than "what should."

Uncovering hidden corporate politics and operational barriers before prompting system logic.

A structural approach to drafting constraints before looking for solutions.

Why the ability to say "no" to AI output is the only defensible skill left for senior designers.

How to train junior team members in critique when they grow up in a generated world.

How to identify which parts of your process should be automated vs. kept human.

Using models to find the blind spots in your strategic proposals.

Structuring an interview where the AI only responds with clarifying questions.

How to define and document "taste" so a team can evaluate generated assets consistently.

Structuring a 5-step evaluation checklist for AI-generated visual concepts.

Why rarity of concept matters more than complexity of execution in a world of infinite generation.

Why the value of professional consulting has migrated from the delivery of solutions to the accuracy of the initial diagnosis.

How to sell and deliver high-value consulting workshops that evaluate a client's operational readiness before implementing automation.