Episode #119
Ep.119 - The Art of Asking Great Questions (And Why We're Losing It) With Larry Robertson
The Art of Asking Great Questions (And Why We're Losing It) The Occupational Philosophers | Episode 119 With Larry Robertson With Larry Robertson: author, innovation advisor, and Inc. Magazine columnist, and founder of Lighthouse Consulting, where he's spent three decades guiding leaders through uncertainty and change. 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. Larry has spent twenty-five years watching the world drift away from real questions and toward statements dressed up as questions. His fourth book, Great Question: The Art of the Ask, is the result. Larry has spent twenty-five years watching the world drift away from real questions and toward statements dressed up as questions which is the subject of his fourth book, Great Question: The Art of the Ask. This episode is about what that costs us, and what we get back when we relearn the practice: noticing, intellectual humility, and the "adjacent possible" as a way of seeing what's one step from where we already are. Timestamps 00:00 – Cold open, curious-eye banter, and Simon's favourite artwork story 00:04 – Introducing Larry Robertson 00:08 – Larry's curious eye: yellow finches, and a window onto Arlington, Virginia 00:13 – Dinner party questions: joy right now, and the big question Larry keeps circling back to 00:17 – Robin Klingler, the World Peace Game, and collective wisdom 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 – The Jeopardy! thought experiment 01:13 – Rapid fire: the manifesto addition, plus book and film recommendations 01:16 – A shoutout to Creative Mornings 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/ Center 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 Key Ideas The Practiced Noticer — Paying attention isn't passive. Larry draws a line between people who simply notice and "practiced noticers" who've turned observation into a discipline, and it's a skill anyone can build. The Adjacent Possible — Borrowed from theoretical biologist Stuart Kauffman, the idea that breakthrough thinking doesn't arrive fully formed. It shows up in workman's clothes, one small step past what you already know. Intellectual Humility Isn't Humility — It isn't about admitting you were wrong. It's accepting that what you know might be incomplete, and that you might have to change because of what comes back to you. Questions Are a Behaviour, Not Just a Skill — Brains are built to do their best work in uncertainty. The questioning instinct is wired in, long before we have the words to ask anything. The Slow Disappearance of the Real Question — Twenty-five years of observation led Larry to a blunt conclusion: more of what passes for questions now are just statements with a question mark at the end. Mattering Over Meaning — The point isn't landing on one big answer at fifty that carries you to ninety. It's staying in the practice of asking why you matter, again and again. Warm Data Versus Cold Data — The numbers on the spreadsheet only tell part of the story. The atmosphere in the room, the thing you sense rather than measure, is often where the real signal lives. Standout Line "What will you realise soon that you already know?"
