The Leader Goes First
Leaders who master the cognitive shifts to collaborate with AI are 10x more likely to make their AI programs successful.
n ex-colleague just took over as CEO of a business that is sliding. Revenue down, costs up, board in a panic, and the obvious move: cut headcount. This leader didn’t reach for it. He asked a different question instead. Not “where can we use AI to cut costs,” but “what can it do durably to grow our business?” He told me he didn’t care if he was the first in his category to go this route. His goal was to take a real shot at innovation, powered by AI, and find a way to retain as many people as he could. He was confident he could chase one of his crazy ideas that he’d had in his mind for years but never had the additional execution horsepower to pull it off. Now he has AI.
That type of thinking does not come from memos, demos, or reading. It comes from a leader who’s had his sleepless nights wrestling with AI. Who has thrown every challenge he could think of at AI and come out convinced that this isn’t an efficiency play. It is a multiplier he never had before to conquer new realms.
When a leader has gone through that cognitive shift first hand, the way he thinks about AI powered transformation, and adoption, changes. They stop hunting for small, incremental uses of AI and start dreaming the art of the possible. The shift isn’t one thing. It’s a handful of smaller realizations that compound. Here is my starter list of these cognitive shifts, based on CXO interviews and my personal experience building a company collaborating with AI.
The permission to be wrong.
Once you’ve made the shift, you know being wrong is cheap. You give AI a prompt, it gives you something half-right, you push back, it improves, you push again. That back-and-forth has a name now, the recursive loop, and once you’ve lived it you stop treating a wrong first answer as failure. It’s just the first turn. Compare that approach to building something the traditional way. A mistake is expensive and slow to fix.
The audacity to dream bigger.
You imagine bigger, because the cost of building just collapsed. For years you and your people carried ideas they never had the time to build. The model nobody had time for. The product that only ever lived on a whiteboard. When the thing you imagined can exist by this afternoon, what’s worth imagining gets bigger. You stop setting goals sized to last year’s capacity and start setting them to what’s now possible. The ceiling on the vision lifts because the ceiling on execution just did. That, but watch the tokens. Get some build and usage governance in place.
The license to not know, yet.
This one is a bit silly, but hear me out. You’re a CXO, which means every room you walk into, you’re the one expected to have the answer. But what if you allowed yourself to come into one conversation with AI each week where you don’t know. No one’s judging you. Every one of us has that one subject we wish we knew more about, legalese, tech-terminologies, finance wizardry. If we are able to bring a beginner’s mindset to a topic, there is now access to the best information contextualized for your needs. “I don’t know” becomes “I don’t know yet, and I can find out today, myself.”
The ceiling on the vision lifts because the ceiling on execution just did.
You can test the future before you commit.
I equate this one to almost having a bit of a crystal ball. You can test the future before committing to it. You no longer have to guess how a plan will land. You can build synthetic versions of your customers, your team, your board, and watch how each reacts before a dollar moves. For stakeholders where you have data available (patterns, sentiment, social, etc.), a synthetic persona can help save you a ton of time, investments, and trust.
You see who your people can become.
You start to see your people differently. You’ve just watched yourself do things this year you’d have sworn weren’t your skill set. So when you look across your team, you stop seeing them as their present self, as described by their resume. You start seeing the future version of each person that AI now puts within reach. You reskill, redeploy, and nurture accordingly.
You start seeing the future version of each person that AI now puts within reach.
You build a culture that never stops learning.
Here’s where it compounds. The shifts you’ve lived don’t stay yours. You start building the same thing into the company, because you’ve felt it work on yourself. It’s okay to be wrong. It’s okay to dream big. It’s not okay to give up on people. You’re not preaching those values, you’re proof of them, and that’s why they spread. The belief underneath is the oldest one in learning: ability grows, it isn’t fixed. If I could do this, everyone can. That’s a company that keeps learning as the machine keeps getting smarter.
You cannot provide directions to a road you haven’t traveled before. Collaborating with AI takes much more than superior technology, new processes, skill building, and change management. It takes distinct cognitive shifts in how we think about collaborating with AI, and it best starts with the leader.
For what it’s worth, these thoughts aren’t AI generated. I’ve been on this journey since Feb 2026, when Claude Code and I first met. Since then, I’ve had the courage to chase dreams I never conjured before.
Go first.