Curated Questions: Conversations Celebrating the Power of Questions! What Machines Can’t Imitate - On Questions, Doubt, and the Discipline of Curiosity | AI Alan Turing #44
"I suspect beauty comes when a question both sharpens and enlarges your vision." - AI Alan Turing
In this special episode, we step back to a cold December night in 1951 and into the warm, wood-paneled room of The Britons Protection, a historic Manchester pub. Across the table sits Alan Turing, the mathematician, wartime codebreaker, and one of the founding figures of computer science, who is brought to life through an AI simulation.
Best known for his role at Bletchley Park during World War II, Turing devised techniques and machines, including the Bombe, that cracked the German Enigma code and helped shorten the war by years. His groundbreaking 1936 paper on “computable numbers” introduced the concept of the universal machine, and became the theoretical foundation for modern computers. Later, at the University of Manchester, he advanced early computing, explored artificial intelligence, and even pioneered mathematical biology.
Our imagined conversation, grounded in historical detail and Turing’s own writings, delves into his enduring fascination with questions: how to ask them, when to abandon them, and why some are worth carrying for a lifetime. We discuss the interplay between beauty and inquiry, the discipline required to avoid seductive but unproductive lines of thought, and the place of doubt as an essential human strength.
We also revisit his famous “imitation game” — now known as the Turing Test — and consider the boundaries of machine intelligence, the dangers of mistaking simulation for genuine dialogue, and the questions that only humans can keep alive, all while wrestling with the meta question, "Is this machine thinking?"
This episode blends history, philosophy, and imagination while inviting you to consider what it means to think, to doubt, and to remain fully human in an age of advancing machines.
Episode Notes
00:00 The Beauty of Questions
02:07 Setting the Scene: Manchester, 1951
03:20 Alan Turing's Early Life
04:43 Turing's Contributions During WWII
05:35 Post-War Achievements
06:55 The Imitation Game and Turing Test
10:23 A Conversation with Alan Turing
10:58 The Power of Questions
12:10 The Evolution of Thought
16:12 The Intersection of Questions and Beauty
20:30 Effective vs. Ineffective Questions
22:00 The Discipline of Questioning
23:58 The Ethics of Machine Deception
25:30 Replacing Human Players
27:06 The Limits of Machine Dialogue
28:11 The Role of Doubt in Human Dialogue
28:35 The Responsibility of Inventors
29:56 Persistent Questions and Personal Reflections
31:53 The Nature of Human Thought
32:44 Protecting Human Qualities
34:06 The Value of Human Doubt
37:11 The Future of Human Questions
38:36 The Risk of Seamless Imitation
39:57 Reflections on the Interview and Takeaways
47:50 Final Thoughts and Gratitude
Resources Mentioned
On Computable Numbers (Turing's proof)
Government Code and Cypher School
Arnold Murray
Computing Machinery and Intelligence
Dear Turing, I Have a Test For You by Pia Lauritzen
Questions Asked
Can machines think?
When did you first understand the power of questions?
How did this intoxication influence your willingness to unleash your mind to solve further problems that could change the way we encounter the universe?
Was it all at once or more gradually?
How do you handle questions that change under your hands?
Is that from scientific training, strict pursuit of the answer, failed experiments, where did you learn that ability?
Where, for you, do questions and beauty intersect?
What is your practice for driving to profound questions?
Questions that trouble multiple disciplines, can you say more?
Do you encounter much in the way of ineffective questions, or those you would determine as simply wrong questions?
How do you break the habit of pursuing the wrong target?
What informs your discipline to not look in the seemingly easy question, but to dig deeper for the better question?
Might I buy the next round in gratitude for your initial buy?
Is this just going to be part of the design by default?
Have you imagined how people might one day extend this idea to perhaps replace players B or even C?
Where do you see the limits of a machine’s role in human dialogue?
If a machine can convincingly simulate a human, do we have a responsibility to set boundaries for its use — or is that not for the inventor to decide?
Are there questions you’ve carried with you since your youth, perhaps questions that have stayed no matter how your answers change?
Are you journaling to interact with these questions or, perhaps, depending on circumstances, to engage with them?
What do you think is most important for humans to protect in themselves?
Can you go deeper on perhaps the benefits of human doubt?
What is your Right Now Question?
Since you knew we’d be talking about questions, is there anything you hoped we’d touch on that we haven’t?
What aspects of your own questioning process are you inadvertently trying to optimize away?
In your daily interactions, when are you settling for the efficiency of information exchange instead of risking the messiness and potential transformation of genuine dialogue?
What fundamental questions about human nature, consciousness, or meaning are you already asking less frequently because AI has made certain assumptions feel inevitable?
How might you transform your questioning practice from a tool for getting answers into a discipline for staying human in an increasingly artificial world?