Advice for the AI Revolution
As orgs resist change, leadership needs courage and humility to embrace what’s coming.

Now I want Twizzlers.
There’s a lot of talk lately about AI coming for your job. For example, here’s an excellent piece in The Atlantic about AI and the future of work; it’s spot-on, and I agree with much of its analysis.
Since we build software with AI at Aboard, we often get asked about hiring and firing. I get it—right now, people are obsessed with how AI could replace people in the workforce. Jack Dorsey’s Block just laid off thousands of people, for example, in order to prepare for an AI future. That’s scary, but my instinct is that a lot of it is performative, too: Look at how prepared we are for the AI revolution! Keep our stock price high!
I don’t think the real change is going to happen at the workforce level. I find myself thinking more and more about how AI could transform the nature of entire companies. Most organizations really suck at dealing with disruptive change. Large, successful orgs that dominate a particular sector or market often fail to react to some disruptive force that shows up out of nowhere. Here are a few examples:
- Kodak vs. digital photography. Most of Kodak’s revenue came from selling and developing film. They actually invented the digital camera in the 70s. But the film money was too good to stop. Fast forward to 2012: Kodak files for bankruptcy, eaten alive by, of all things, the Canon Powershot.
- Blockbuster vs. Netflix. I got to know the Blockbuster manager in Canarsie, Brooklyn. Why? Because I wanted Terminator 2 on DVD before anyone else. I’d grab a giant strawberry Twizzler pack on the way out. Blockbuster’s cash cow was late fees and junk food by the cash register. Netflix mailed you discs, which seemed slow and goofy to me. I don’t need to rehash what happened: 2010 bankruptcy.
- BlackBerry vs. smartphones. BlackBerry truly understood the business customer, and they knew their moat: That Chiclet keyboard and integration with secure corporate email boxes. Then came the iPhone. Apple’s trojan horse was a consumer entry point that proved irresistible for everyone, including companies. When app ecosystems eventually took hold, Blackberry’s closed environment rendered it antiquated.
The classic book on this, of course, is Clayton Christensen The Innovator’s Dilemma. There is one statement in there, that I keep coming back to:
The very processes and values that constitute an organization’s capabilities in one context, define its disabilities in another.
Kodak got really good at tracking the demand and fulfillment of camera film. They invested in…better quality photographs with brighter colors! They were optimized for what they’re good at.
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I call this sort of institutional muscle memory procedural debt. The org chart and the processes that pulse through it are an immune system that protects the body from drastic change. But at the same time, drastic change is coming. Unless your industry involves deep tissue massages or really delicious tacos out of a truck, you will be affected (for now—frankly the massage robot landscape looks like it’s poised to grow).
So when people ask me, “Can I fire my engineering team?” I don’t actually entertain that conversation. It’s too soon. Instead, I give them this advice:
- Don’t just cut costs, invest aggressively. Cutting jobs because AI can take over tasks is not a strategy. It is a temporary sugar high. The world is not just delivering efficiency; it’s also opening up opportunities for transformational change. Having fewer people does not position you to innovate. Retraining current employees and hiring new ones does.
- Don’t use AI to do shitty things faster. Related to the first point, your current processes are products of your past. Sure, you might be able to do them faster and better with AI, but rethinking how things work altogether leads to real competitive advantage. Remember: Your competitors are out there and they’re traveling light, free from all your procedural debt.
- Care less about technology. We can all thank Claude Code for the remarkable grassroots revolution we’re witnessing. But be wary: Engineers are under threat like everyone else, and they will defend their territory. To protect their turf, they will create friction and obfuscate. The two most powerful words an executive can use right now: “Why not?”
- Generate business urgency. Everybody is hunkered down. It’s not just your front-line employees; your executives are nervous, too. Mind you, there is urgency: Personal urgency, departmental urgency, Chicago satellite office urgency. But business urgency can only come from the top. It will take real work to get everyone to worry less about themselves and their teams and start aligning with the business. And it will require a particular kind of leadership that’s willing to make meaningful change happen.
- Go outside for help. Even before AI, the #1 reason business leaders go outside is because the org refuses to adapt, or won’t adapt fast enough. It’s always been very hard to get large swaths of an org to reset and align around a new set of goals. The AI challenge today is a whole other level of disruption. Going outside allows you to route around that stubborn procedural debt, and it’s often a good shot in the arm. (Disclaimer: The parent company of this newsletter is Aboard, a top-tier AI solution platform and consultancy.)
I’m an attorney by education, and one of the first things you learn in law is a company is a “fictional individual,” imbued with many of the rights and responsibilities of actual people. While we’re all debating whether AI will replace workers, it’s worth remembering that companies are people, too! Stubborn, slippery, deeply manipulative people that will hold onto their place in the world unless leadership has the courage and humility to embrace what’s coming. It’s going to be a wild ride. I believe we’ll get through it. But if you see change coming, pay attention. Nothing is going to look quite the same.