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Conversations with a Machine: Diving deep into real human problems with a not-so-human partner
As a Senior Partner in a global consulting firm, I’ve spent the last year learning and using AI to improve the quality of my work, reduce the time it takes to generate deliverables, and to improve the bottom-line profitability of our business. During that time, I’ve had the opportunity to explore and experiment with several AI Tools including ChatGPT, Copilot, Gemini, HeyGen, ElevenLabs, NotebookLM, Midjourney, Otter.ai, and Fireflies, and have recently begun my exploration of Agentic tools in earnest.
However, as I began to dive more deeply into conversations with Generative platforms about work topics, I started to cross into “non-work” side conversations. For example, exploring the process of organizational culture change for one customer ultimately took me down a rabbit hole that led me into motivation, coaching, and therapy, and this led me to Carl Jung and…well, you know how rabbit holes work online!
However, these forays into non-work topics turned out to be incredibly fascinating and fruitful. So, I decided to set aside 90 minutes every weekend to select one topic, open a prompt dialog, and just let it take me where it did.
Now let’s be clear. I am neither a philosopher nor a professional sociologist. So, these conversations are far from being airtight arguments and certainly should not be considered treatises of any kind! I don’t think we discovered any ultimate truths and no topic was covered wholly. But at the same time, that was not the point. Take these conversations for what they are, real-time conversations through which to question, learn, challenge and practice. They are a beginning.
With that said, what I found was that these conversations were truly inspiring to me.
They helped me to rethink and clarify all sorts of ideas that I had about the modern world. They also gave me a totally new understanding of, and empathy for, Artificial Intelligence - how to dance with AI to create something beautiful, rather than frightening or threatening. The conversations helped give me a hands-on understanding about how the future could include both humans and AIs and why that world might be better than one without the other.
It also created a safe space to explore ideas with someone else who would challenge me without being a troll and who was not so invested in any worldview that I could not challenge them effectively.
This book is a curated and mostly uncensored transcription of those dialogs. I hope you will find these dialogs fun, useful, challenging (in a good way), and inspirational. Like me, you might even learn something about AI that cannot be learned other than through real interaction.
However, as I began to dive more deeply into conversations with Generative platforms about work topics, I started to cross into “non-work” side conversations. For example, exploring the process of organizational culture change for one customer ultimately took me down a rabbit hole that led me into motivation, coaching, and therapy, and this led me to Carl Jung and…well, you know how rabbit holes work online!
However, these forays into non-work topics turned out to be incredibly fascinating and fruitful. So, I decided to set aside 90 minutes every weekend to select one topic, open a prompt dialog, and just let it take me where it did.
Now let’s be clear. I am neither a philosopher nor a professional sociologist. So, these conversations are far from being airtight arguments and certainly should not be considered treatises of any kind! I don’t think we discovered any ultimate truths and no topic was covered wholly. But at the same time, that was not the point. Take these conversations for what they are, real-time conversations through which to question, learn, challenge and practice. They are a beginning.
With that said, what I found was that these conversations were truly inspiring to me.
They helped me to rethink and clarify all sorts of ideas that I had about the modern world. They also gave me a totally new understanding of, and empathy for, Artificial Intelligence - how to dance with AI to create something beautiful, rather than frightening or threatening. The conversations helped give me a hands-on understanding about how the future could include both humans and AIs and why that world might be better than one without the other.
It also created a safe space to explore ideas with someone else who would challenge me without being a troll and who was not so invested in any worldview that I could not challenge them effectively.
This book is a curated and mostly uncensored transcription of those dialogs. I hope you will find these dialogs fun, useful, challenging (in a good way), and inspirational. Like me, you might even learn something about AI that cannot be learned other than through real interaction.
301 pages, Kindle Edition
Published July 2, 2025
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