For every new manager or any manager who suddenly woke up in the age of algorithms as a first-time manager…
Let me introduce you to Wally Von Picklesworth, yes, that is the real name of our artificial matrix hero. And no, this is not satire (well, maybe just a little).
Wally is 58. He has two master’s degrees, a stable marriage, and a drawer full of ties he hasn’t worn since COVID. He recently became a first-time CEO at a charmingly unstable pharma company called Pharmageddon Biotech, best known for developing a hangover drug that accidentally cured two types of acne and one midlife crisis.
So far, so good, until Wally walked into his first strategy meeting and someone said,
“We will run that through the LLM.”
Wally blinked.
“Lovely. What is an LLM?”
“Large Language Model.”
“Oh. I thought it was a law degree.”
Let’s get one thing straight.
Wally is not stupid. He has survived three recessions, two mergers, and one office fire caused by a fax machine. But like many Baby Boomers, Gen Xers, and even elder Millennials, he is now, suddenly, a first-time manager in an AI-driven world.
And here is the twist: he is actually handling it better than the 30-year-olds pretending they know what they are doing.
While the digital natives were busy feeding their entire business plan into ChatGPT, Wally did something radical.
He asked questions. Real ones.
“Can we trust this AI model not to lie?”
“Will regulators accept a machine-generated trial report?”
“Do I now need to supervise a robot in addition to my CFO?”
The room fell silent.
Then came the magic word: respect.
You see, the real problem is not AI.
It is pretending you understand AI when you do not.
And that is the epidemic, not just in startups and tech-bro circles, but across every industry dressing up cluelessness in futuristic PowerPoints.
Wally chose not to fake it.
Instead, he launched a weekly “Dumb Questions, Smart Answers” session.
No jargon. No ego. Just learning.
Guess what?
It turned his company around.
People started thinking again. Collaborating. Challenging the hype.
And he, a so-called dinosaur, became the most adaptive person in the room.
Everyone is a first-time manager in the AI Age.
The ones who thrive are not those born with screens in their hands.
They are the ones who know what they do not know and are not ashamed of it.
That is the core of leadership.
If you think age disqualifies you from navigating AI, think again.
Experience still matters. Context still matters. Common sense still matters.
(And, by the way, so does knowing when not to listen to a machine.)
As I wrote in Labyrinth of Management, real leadership does not come from tools.
It comes from the courage to face uncertainty and the humility to ask,
“What am I missing?”
Wally Von Picklesworth did not just survive the AI revolution.
He led it.
Corduroy and all.
—
If you enjoyed this article, you can dive deeper into real-world leadership lessons and behind-the-scenes stories in my book Labyrinth of Management—available now on Amazon.
For more stories, reflections, practical leadership tips, and to stay updated you can follow me on Instagram, X (Twitter), and Facebook.