Artificial Intelligence Podcast: ChatGPT, Claude, Midjourney and all other AI Tools
Aug 31, 2026 · 30 min · 11 segments
Everyone was told to adopt AI, tried it, got burned — so why do enterprise AI rollouts keep failing? Jonathan Green talks with organizational strategist Rob Lion about the real reasons big AI…
Rob LionGuest
Jonathan GreenHost
We're making the same mistakes here that a lot of companies make with their first hire.
Like the first time someone hires a VA or remote employee, they go, manage my social media.
And it's like, well, what's your posting cadence? What's your frequency? What's your style? What's your measurement of success? And if someone doesn't know what success looks like or what target, they don't know if they're doing a good or bad job.
If you don't have a clearly defined process for it to automate, accelerate, replicate, then it's going to fail, guaranteed, like right out the gate.
And then if you don't have a measure of success, which is, well, what does a good presentation look like? What's your measure of success for a presentation? And what's your process? This is the most important part.
How did you make that presentation? There's nothing worse than when someone shows me an output and then won't give me the prompt they used.
And it's like, if you give me a cake and say, mate, here's the ingredients, make it.
If you're a master chef, I don't know how someone can taste something and they know how it's made.
But it's the same thing to try and reverse engineer a process because, like you said, these AI tools are constantly changing and the order in which you do things makes a huge difference.
And there's always this micro step that gets lost unless you watch someone doing it, which is why we all love watching a video instead of a set of instructions, because the one person the person would have forgot to write down is like the most important step.
So in the same way, if you don't have your process of how you use this tool codified, you don't have the measurement of success codified, it's impossible that you even consider success.
Like if you gave the same set of instructions to a new employee, would you expect them to be able to succeed when you go, make a bunch of slides, what should they look like? I don't know, good? How many should I make? The right number, like there are not enough instructions there for them to succeed and it's the same thing when you're giving a new tool to an employee.
I also think that like, it's not clear why, often the why we're switching to this tool or what's the benefit to the employee is ever explained.
Because I've seen some companies that go, now that we have AI, we want you to do twice as much work.
We're making the same mistakes here that a lot of companies make with their first hire.
Like the first time someone hires a VA or remote employee, they go, manage my social media.
And it's like, well, what's your posting cadence? What's your frequency? What's your style? What's your measurement of success? And if someone doesn't know what success looks like or what target, they don't know if they're doing a good or bad job.
If you don't have a clearly defined process for it to automate, accelerate, replicate, then it's going to fail, guaranteed, like right out the gate.
And then if you don't have a measure of success, which is, well, what does a good presentation look like? What's your measure of success for a presentation? And what's your process? This is the most important part.
How did you make that presentation? There's nothing worse than when someone shows me an output and then won't give me the prompt they used.
And it's like, if you give me a cake and say, mate, here's the ingredients, make it.
If you're a master chef, I don't know how someone can taste something and they know how it's made.
But it's the same thing to try and reverse engineer a process because, like you said, these AI tools are constantly changing and the order in which you do things makes a huge difference.
And there's always this micro step that gets lost unless you watch someone doing it, which is why we all love watching a video instead of a set of instructions, because the one person the person would have forgot to write down is like the most important step.
So in the same way, if you don't have your process of how you use this tool codified, you don't have the measurement of success codified, it's impossible that you even consider success.
Like if you gave the same set of instructions to a new employee, would you expect them to be able to succeed when you go, make a bunch of slides, what should they look like? I don't know, good? How many should I make? The right number, like there are not enough instructions there for them to succeed and it's the same thing when you're giving a new tool to an employee.
I also think that like, it's not clear why, often the why we're switching to this tool or what's the benefit to the employee is ever explained.
Because I've seen some companies that go, now that we have AI, we want you to do twice as much work.
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