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August 17, 2026 • 81 mins

The Art of Asking Great Questions (and how not to lose it)

The Occupational Philosophers | Episode 119 - Larry Robertson 

Larry Robertson is an author, innovation advisor, and Inc. Magazine columnist and founder of Lighthouse Consulting, where he's spent three decades helping organisations successfully manage growth. He's a graduate of Stanford and Northwestern's Kellogg School of Management; he was named a US Fulbright Scholar in 2021, (a rare distinction for someone working outside academia). If that's not enough, he's also an Adjunct Professor! 

In his work, he's watched the world drift away from real questions and toward statements dressed up as questions, which, unsurprisingly, is the subject of his fourth book, Great Question: The Art of the Ask. This episode dives into what that lack of curiosity can cost us. Importantly, the book explores what we get back when we relearn the practice of noticing, intellectual humility, and the "adjacent possible" as a way of seeing what's one step from where we already are. It also unearths the bigger question of what it means to be human.  Larry is possibly the world's nicest man, and Simon and John hope you enjoy listening to the show as much as they did recording it. There are so many gems here. 

Timestamps

  • 00:00 – What's caught your curious eye and Simon's favourite artwork story
  • 00:08 – Larry's curious eye: yellow finches, and the joy of seeing
  • 00:13 – Dinner party questions: The big question Larry keeps circling back to
  • 00:20 – Larry's Venn diagram, and his to-ask list (with an assist from Mary Oliver)
  • 00:25 – Where the new book started: the pattern across his first three books
  • 00:29 – The 25-year observation: statements replacing real questions
  • 00:32 – Four things a question is: an invitation, a frame, a behaviour, an identity
  • 00:37 – Noticing versus the practiced noticer
  • 00:40 – Stuart Kauffman and the adjacent possible
  • 00:43 – Slow looking, the National Gallery, and Claire Bown's "The Art Engager"
  • 00:47 – Training medical students by having them diagnose art
  • 00:50 – Intellectual humility: the Hero's Journey, three levels, and the mantras for practicing it
  • 00:58 – Warm data versus cold data, and reframing the data-centre problem
  • 01:02 – Why the book matters: mattering, meaning, and being a questioning species
  • 01:07 – Jeopardy! Possibly the world's best ever thought experiment
  • 01:13 – Rapid fire: the manifesto addition, plus book and film recommendations
  • 01:18 – What's next for Larry, and where to find him

Live Links

Larry Robertson

  • Website: https://lrspeaks.com/
  • Great Question: The Art of the Ask (Amazon): https://www.amazon.com/Great-Question-Getting-More-Really/dp/0983757461
  • Lighthouse Consulting: https://lighthouse-consulting.com
  • LinkedIn: https://www.linkedin.com/in/larryrobertson3rd/
  • Column — Inc. Magazine: https://www.inc.com/author/larry-robertson
People & Work Mentioned
  • World Peace Game Foundation (Robin Klingler): https://worldpeacegame.org/
  • Stuart Kauffman, theoretical biologist and originator of "the adjacent possible": https://en.wikipedia.org/wiki/Stuart_Kauffman
  • Claire Brown — The Art Engager / Thinking Museum: https://thinkingmuseum.com/
  • Project Zero, Harvard Graduate School of Education: https://pz.harvard.edu/
  • Centre for BrainHealth, UT Dallas (art-based medical student training): https://centerforbrainhealth.org/
  • Temple Grandin: An Open Door (documentary): https://www.templegrandindocumentary.com/
The Occupational Philosophers
  • Website: https://www.occupationalphilosophers.com
  • Substack: https://occupationalphilosophers.substack.com
  • John — Bowland Consulting: https://www.bowlandconsulting.com
  • Simon — simonbanks.com.au: https://www.simonbanks.com.au
Standout Line

"What will you realise soon that you already know?" As always:  Stay curious, play more, have fun, make stuff, and as you leave the door, date life as always, stay curious, play more, have fun, make stuff, and as you leave the door, date life. 

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