The Art of Asking Great Questions (And Why We’re Losing It)
The Occupational Philosophers | Episode 119
With Larry Robertson — innovation advisor, author, and founder of Lighthouse Consulting, and the author of “Great Question: The Art of the Ask,” his fourth book after three decades advising leaders through uncertainty and change.
Larry has spent twenty-five years watching the world drift away from real questions and toward statements dressed up as questions. 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 realize soon that you already know?”