This is the Leadership Journey series on the Choosing Leadership Podcast.
I believe we all have a lot to learn from each other’s stories – of where we started, where we are now, and our successes and struggles on the way. With this series of interviews, I attempt to give leaders an opportunity to share their stories and for all of us to learn from their generous sharing. If you know a leader whom you would like to see celebrated on the show, please send me a message on LinkedIn with their name.
What happens to the first rung of the career ladder when AI takes over the entry-level work?
In this conversation, Oliver Pickup, a journalist of more than 20 years who now calls himself a human work evolution storyteller, shares how the launch of ChatGPT gave him what he calls FOBO, the fear of becoming obsolete, and how it pushed him out of his comfort zone and onto the speaking stage.
Oliver and Sumit explore why he sees three tribes (AI martyrs, AI zealots and AI agnostics), why he treats AI as a smart intern while keeping the creative process and the end product his own, and why a world drowning in AI slop will reward lived experience, personality and detail.
For leaders, Oliver raises a pointed warning about the vanishing first rung: if companies hand all the entry-level work to AI and stop bringing in young talent, what will their garden look like in five years? He also explains why people need a vision and proper training before you hand them the keys to a Formula 1 car.
Underneath it all is a family thread: how becoming a father reset his values, why he builds Friday afternoons around watching his son play rugby, and why reading the bedtime story together still counts, even when AI can write one in a blink.
You can find Oliver Pickup at the links below
In the interview, Oliver shares
- “I want humans to be the carpenter rather than the nail at the other end of the hammer.”
- “AI is making many of us a hamster going faster on a faster wheel. The more tech you throw at something, the busier people are.”
- “There are AI martyrs who think AI will take their job, AI zealots who defer to it for everything, and AI agnostics who don’t fear it and don’t worship it. They see it as a tool.”
- “I use AI as a smart intern to help with the legwork, but the creative process and the end product are all mine.”
- “Generative AI is the average of the average, so it’s clear to see when something isn’t up to the standard a human would produce.”
- “The heart skills, the seven C’s, are collaboration, compassion, communication, courage, critical thinking, creativity and curiosity. They matter more as the machines get stronger.”
- “I just don’t think we should be so ready to give all the keys to the castle to AI.”
- “We need that lived experience. We need that messiness. We need that friction to really understand a problem.”
- “If you don’t water the garden with young talent, in five years’ time you’re looking at a garden that is completely barren.”
- “AI can write a bedtime story in a blink, but it’s taking the time to read it with her that truly counts in the end.”
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