The Great AI Divide — Part III
Your People, Not Your Tech, Will Cross the AI Divide
I'm a CTO and founder with nearly two decades of experience driving growth and transformation through technology. At Stronghold Investment Management, I led the development of a systematic real asset trading platform and modernized everything from Salesforce strategy to custom cloud-native infrastructure. My background spans commercial real estate, e-commerce, and private markets — always focused on delivering innovation, velocity, and meaningful business outcomes. I hold a PhD in Theoretical & Computational Biophysics and was recognized as a Google Developer Expert in Cloud. I build high-trust, high-output teams. I’ve rebuilt broken cultures, hired top-tier engineers, and helped early-stage and PE-backed companies scale with confidence. System modernization is my specialty — not just upgrading software, but aligning teams and infrastructure with what the business actually needs. Currently, I lead client engagements through Heavy Chain Engineering and am building Newroots.ai, an AI-driven relocation advisory platform.
We’ve covered the Great AI Divide, covering the MIT report that 95% of companies are failing to get any real value from AI. I've also established that I don't think this is a technology problem; it’s a process problem. Most initiatives fail because they lack the rigorous planning and clear specifications that have always been the bedrock of good engineering.
But let’s say you fix that. You start writing clear specs. You define your workflows. You’re still missing the most critical piece of the puzzle, and it’s the one that’s most infuriating: you’re forgetting how to lead.
The Wharton report calls this “The Human Capital Lever,” but what it’s really describing is a catastrophic failure of change management. This is the final, and most important, reason why the 95% are failing. They think they found a magic wand to do the thinking for them, and in the process, they’ve abandoned decades of established practice on how to lead people through change. Even as AI usage becomes mainstream, the report finds that training budgets and confidence in that training are slipping. Think about that. Just as the most powerful tool in a generation is being deployed, we’re becoming less confident in our ability to teach people how to use it.
It gets worse. 43% of leaders see a risk of declines in skill proficiency. They’re worried that by relying on AI, their teams will forget how to do their jobs. (Sidebar: There's a corollary here from the world of DevOps and automation. As we automate more and more the value of the SME increases because that's the person who can fix these larger systems when they break. Like I said, use your freed up time to elevate your thinking.)
Here’s the thing: they’re not wrong to be worried, but they’re diagnosing the wrong disease. The problem isn’t that AI makes people dumber. The problem is that when you deploy a systemwide tools with lack of forethought, you can’t possibly train for it effectively. People give up easily because they were set up to fail from the start.
Your Training is Broken
So why is confidence in training slipping? Because watching a webinar on “10 Cool ChatGPT Prompts” doesn’t work. The kind of training that creates self-sufficient, AI-powered teams is messy, hands-on, and real. It’s about showing them your own process, failures included. It’s about setting up a sandbox and letting them try, explore, and report back.
It’s about coaching them through that initial frustration until they have their own “this just saved me weeks” moment. Once they feel that, you’ll never have to convince them to use AI again. They’ll be hooked. They'll become more productive and happier, which will be noticed by others. I've seen this positivity spread. It's so satisfying to watch.
The divide between the 5% and the 95% isn’t a technology gap. It’s a culture and a mindset gap. The companies that are winning are the ones that are cultivating a culture of pragmatic persistence. They’re not trying to replace human thinking; they’re focused on elevating it. They understand that the most valuable skill in this new era is the ability to think critically, define a problem with absolute clarity, and then use AI as a tireless, infinitely scalable intern to execute the solution.
Forget the hype and the fear. The AI revolution should be a human revolution. It should be what frees us to elevate our thinking and put our grey matter on larger matters. But that can only happen with leadership. It requires a return to the fundamentals of craftsmanship, planning, and disciplined change management. The question isn’t whether your people have the right mindset; it’s whether you have the discipline to lead them across the divide.
