Analyse Podcast

“What is your origin story and how did you get started in your career?”

A classic opening move, used to establish the guest's foundational experiences and motivations.

“What did you see in [Place] at [Time] that others in [Another Place] missed?”

This question seeks the specific, non-obvious insight that sparked the guest's successful venture or idea.

“What is the single question you have been chasing across your different roles as an operator, scholar, or author?”

Leong uses this to find the unifying thread in a guest's multi-faceted career.

“Which lesson from your mentors do you constantly test your own arguments against?”

This question reveals the guest's intellectual influences and their process for self-critique.

“What became visible to you in your role only after you stepped away from it?”

This probes for insights gained from a critical distance or a significant change in perspective.

“What's the most important thing about [Group/Topic]'s thinking that gets lost in translation for a Western/global audience?”

He asks this to surface a key, nuanced insight from a guest with deep regional or subject-matter expertise.

“Why did you begin your book with a personal story about your daughter?”

This explores the narrative strategy and emotional core behind the guest's professional work.

“Why do you think [Washington/Silicon Valley/etc.] has been asking the wrong question for the last decade?”

This question is designed to tee up the guest's core contrarian argument or the central thesis of their book.

“Can you explain the core tenets of your book and define the term '[Innovationism]?'”

A direct request for the guest to articulate the central framework of their work for the audience.

“Which aspect of your framework—[A], [B], or [C]—does the most work?”

He asks this to force the guest to weigh the components of their own model, revealing what's most critical.

“With a company like [OpenAI] potentially going public, what is an investor actually buying if there's no clear moat?”

Leong often uses this format to challenge the fundamental business model or valuation of a company in the headlines.

“What counter-intuitive lesson have you learned about [Topic] that most leaders get wrong?”

This is a direct prompt for a contrarian insight drawn from the guest's specific, hard-won experience.