Chris Hay, AI Technologist & Futurist
When it comes to pitching, most people think about perfect slides, rehearsed lines, and the sweaty palms that come with trying to stick the landing. But as anyone who’s seen Chris Hay in action will tell you, great pitching rarely looks like a rigid script — and increasingly, it doesn’t happen without a little help from artificial intelligence.
Chris and I know each other well through our time at IBM, where I’ve watched him pitch complex ideas to huge audiences without ever appearing tied to a slide deck. He describes himself as a “technologist, futurist and disruptor” — and if you listen to this episode, you’ll quickly see why. While he humbly claims he doesn’t ‘do pitching’, what he actually does is convince people to think differently about technology, the future, and how to adapt — and that, in my book, is pitching in its purest form.
The Human vs. AI Paradox
I wanted Chris on the show not because we needed another AI hype session, but because he’s refreshingly candid about what AI can and can’t do — especially when it comes to human connection. As someone who lives at the sharp edge of emerging tech, Chris knows better than most how quickly AI is changing the landscape. But he’s also quick to remind us that pitching is, at its heart, a human conversation.
In the episode, we dig into what happens when you bring AI into your pitch process — not as a replacement for your voice, but as a tool to shape ideas faster, polish drafts, and even pressure-test your slides from the audience’s perspective. Chris jokes that AI can do a lot of what he does, except stand on a stage and read the room in real time — and that’s precisely where your irreplaceable edge lives.
Structured Unstructured: How Chris Pitches
One of my favourite parts of this conversation is hearing Chris describe his so-called “structured unstructured mess” approach to pitching. He spends hours drafting and organising a story, often building 60 to 100 slides — but when he’s in front of an audience, he might only use ten. He never hands his slides over beforehand and never locks himself into a rigid order. Instead, he pivots and responds based on audience signals: who’s leaning in, who’s drifting off, and where the energy is heading.
This is such an important lesson for anyone who feels chained to a script. The real magic of pitching, as Chris shows, is that you can only plan so much. The rest is reading the room and trusting your expertise.
