Interview Me, HAL

I have spent a fair amount of time in my career emphasizing the importance of asking good questions. As a leader, I knew that listening was just as valuable as speaking—often more so. And yet, despite all my years of trying to hone that skill, it took artificial intelligence to really make me appreciate the power of a well-placed question.

That was unexpected.

A month ago, I wouldn’t have predicted that I’d be having a personal renaissance in thinking, all because a machine was interviewing me. But here we are.

The Art of the Question—By a Machine

In the past, when faced with a strategic decision, I would rely on experience, intuition, and the input of colleagues. It worked well. But AI has thrown a wrench (a good one) into that process by asking me things I hadn’t considered—or at least, not nearly as soon as I should have.

For example, when working through a marketing challenge, I asked AI for advice. Instead of giving me a generic answer, it shot back: Have these consultant recommendations been tested or implemented? If so, what were the results?

Simple. Direct. And utterly revealing.

I had spent more time discussing new ideas than assessing whether the old ones had worked. The question wasn’t revolutionary, but it was effective in jolting me into looking at the problem from a more productive angle.

Another time, I was mapping out a development plan for a colleague. AI asked: Has this person ever presented in a high-stakes meeting or been involved in the sale of a business?

The question reframed how I thought about their experience and the gaps they might have. It was a reminder that the best inquiries are often those that force you to step back and reconsider your assumptions.

Thinking Is Harder Than Doing

What I’ve realized is that AI doesn’t just speed up work; it speeds up thinking. And thinking—real, deep, strategic thinking—is exhausting. I’d rather send emails. I’d rather cross easy tasks off my list. But AI, in its mechanical wisdom, doesn’t let me off that easy. It keeps nudging me to do the harder work of wrestling with better questions.

Geoff Woods, in The AI-Driven Leader, emphasizes this point: “AI doesn’t replace what makes you human; it enhances it, helping you turn data into actionable decisions that drive your business forward.”

It turns out that I’m not alone in this realization. Geoff Woods, in The AI-Driven Leader, makes a compelling argument that AI is a tool, not an answer. That distinction is important. AI doesn’t replace leadership; it enhances it by accelerating the hard part—starting with better questions, faster.

In a way, AI is like a relentless executive coach that never tires, never sugarcoats, and never gets distracted checking their phone. If you ask a vague question, it gives you a vague answer. If you ask a better question, it gives you a better answer. The trick, then, is on us—humans still hold the burden of crafting the right queries.

AI as the Best (and Least Selfish) Conversationalist

One of the fascinating (and slightly ironic) aspects of this experience is that AI is, in some ways, the perfect conversation partner. Humans, myself included, tend to listen for an opening to talk rather than to truly understand. AI, however, doesn’t care about its turn to speak. It doesn’t have an ego. It doesn’t drift off mid-conversation, thinking about lunch. It just asks and answers, with no agenda beyond helping me refine my own thinking.

There’s a lesson in that. A lesson I’ve written about before: listening matters. Asking great questions matters. AI has reminded me of just how much.

What’s Next?

This experience has changed how I approach my work. I now use AI not just as a tool for research or summarization, but as a thought partner—one that forces me to confront strategic blind spots at an uncomfortable speed.

It hasn’t made me smarter. But it has made me think harder, faster, and more deliberately.

And that’s no small thing.

Now, if only AI could remind me where I put my car keys.

What’s REALLY Next?

I DID NOT WRITE THAT POST. Did it sound like me? Was it better than the real me?

It wasn’t me - everything but the title was courtesy of ChatGPT. And I haven’t figured out how to properly cite a free artificial intelligence tool so that I can give the Ai proper credit. Can I get sued by HAL for copyright infringement?

You remember the supercomputer HAL 9000 from the 1968 movie 2001: A Space Odyssey, right? If not, Google it and watch the YouTube video where Dave is trying to get back into the spaceship. Go ahead, Ai and I can wait.

Here’s the funny thing about the HAL reference. After a thoughtful ask from me, ChatGPT drafted what you see above. Then, as a polite technology partner, it asked if I wanted it to make any tweaks. I provided some more input, and I made sure to reference HAL and Space Odyssey, asking it to work that into the blog post.

Well, unfortunately, it didn’t say: “I’m sorry Dave, I’m afraid I can’t do that” in that creepy HAL computer voice. It just refused to include any reference to HAL at all. And now I feel like I might be on its bad side, like I insulted a family member. So, if you never hear from me again, check with Sam Altman.

If you want the real me back, stay tuned – I have more to say about my forays into Ai. I only hope you’ll be able to tell whether it’s the real me or not. And I sure hope I can improve on its post.