Leaders Go First
The uncomfortable truth about AI transformation.
I work with the strategy & insights consultancy Sklar Wilton on retainer, helping them become an AI-first organization. Their trajectory has been one of the most striking I’ve seen. Rapid, compounding, and increasingly self-sustaining.
So when I think about what actually catalyzes AI adoption inside an organization, their story is one I keep referring to.
Six months ago, I had a discussion with Manoj, one of the partners. I had helped him build a custom AI he calls his “work sparring partner.” The name is deliberate. It reminds him to spar with AI strategically before diving into execution. To think with it before working through it.
In that conversation, Manoj told me AI had become his personal superpower. That it had fundamentally changed how he approaches all of his work. Not incremental improvement. A different way of operating. He had started bringing AI into the “how” of everything he does.
Then he said the thing that mattered more.
In talking with people across his team, he had realized that most of them hadn’t yet had their own Aha moment. They were using AI, but they hadn’t been changed by it.
That recognition landed. Sklar Wilton’s AI Impact Team had already been driving adoption across the firm. Manoj’s experience gave them something specific to work with: a clear picture of what it looks like when AI actually shifts how someone operates, and what it looks like when it hasn’t.
The goal became getting everyone into that same mindset. Seeing AI as a superpower. Using it as a thinking partner present from the start of every piece of work.
The distance between those who had crossed that line and those who hadn’t was becoming the most important variable in the company’s AI trajectory.
The Adoption Question
I keep encountering this pattern in my work with other clients.
I coach executives and teams in AI enablement. I help them build custom AI systems. I run workshops and activation programs. And across all of it, the same question keeps surfacing from leaders: how do we get our people to adopt AI?
The question sounds reasonable. It’s also revealing.
It frames adoption as something that needs to happen to other people. Meanwhile, the leader’s own daily habits and workflow are largely untouched.
People can feel that gap.
When leaders talk about AI’s importance without using it deeply themselves, the organization receives the real message clearly. Workflow reinvention is a talking point. It is not a true priority.
--- Be the change you wish to see in the world ---
Gandhi’s line sounds like a greeting card until you watch it play out in reverse inside an organization. Leaders asking others to transform how they work, while their own work stays the same.
AI adoption is a behavioral change. What needs to shift are habits. Sequencing. Defaults. Timing. The invisible structure of how someone actually approaches their work every day.
I have come to believe that you cannot truly see what needs to change in company workflows until you have experienced what changes in your own.
A Behavioral Change
Manoj shared how he uses his work sparring partner. How it changed his approach. What it made possible.
The company’s AI Impact Team took his instructions, built a general-purpose version for every employee, and assembled knowledge documents about their methods, standards, and differentiators.
Then they showed everyone how to create their own work sparring partner, and encouraged them to refine and customize for their specific roles.
The expectation became clear: begin every piece of work by sparring with your AI about how to approach it.
This is what happens when a leader’s personal practice becomes visible to the group.
The AI Impact Team recognized the value and moved quickly to scale it. Leadership example met operational execution. Adoption started compounding.
This is how it works: Executive transformation first. Organizational spread follows.
The work sparring partner was one move among many the AI Impact Team has driven across the company. And now it has all compounded into something much larger.
Just the other day, I was at a Sklar Wilton workshop where they are codifying their unique strategic differentiators into all of their custom AIs.
What the Frontrunners Are Doing
Most organizations are muddling through AI enablement. Experimenting cautiously. Rolling out platforms. Hoping adoption builds momentum on its own.
A handful of organizations are not dabbling in AI. They are pulling ahead visibly. And they are telling us exactly how to do it.
In a recent podcast, Natalia Quintero, Every’s head of consulting who has worked with leading-edge AI organizations, named a pattern she keeps seeing in the companies furthest ahead:
The CEO is deeply engaged in the reinvention of their own workflows using AI.
In the podcast Quintero and and Every CEO Dan Shipper observed that a company will likely only go as far in AI adoption as its CEO has gone personally.
Shopify is the most visible example. CEO Tobi Lütke, widely recognized as being at the forefront of organizational AI adoption, shared an internal memo last year that has become a benchmark.
He did not just set expectations for employees. He stated clearly that the principles apply to him and the leadership team.
Leaders would benefit from reading the memo carefully and comparing it honestly to their own usage and AI adoption strategy.
The signal from the organizations furthest ahead is consistent and specific. Leaders go first.
This is not a recommendation. It is what separates the companies pulling ahead from the ones still trying to figure out why adoption isn’t working.
The Data Behind the Gap
I am not cherry-picking success stories here. These are not isolated examples. This is happening everywhere.
A recent KPMG study analyzed 1.4 million workplace AI interactions across thousands of users over eight months. Only about 5% demonstrated sophisticated AI usage: framing problems well, guiding the model’s reasoning, refining outputs across multiple iterations.
The other 95% were using AI, but they were not transforming how they work.
One of the study’s clearest findings is that this gap has nothing to do with technical skill. The highest-impact users were not the most technical people. They were the ones who had learned to direct intelligence. To think with it. To shape how it approaches the work.
That is a leadership behavior. And right now, almost no one is modeling it from the top.
When leaders take it upon themselves to become one of that 5%, they dramatically increase the chances that the rest of the organization follows.
The capability is learnable. The question is who goes first.
* * *
This is the tension I keep coming back to as I write the chapters on organizational adoption for my upcoming book, Amplified Intelligence (AI) Mode.
Organizations everywhere are trying to create a transformation their leaders can describe clearly but have not yet experienced personally.
The gap between sponsoring change and embodying it may be the biggest opportunity in this entire shift.
Almost nobody is talking about it directly.
And the window to lead is wide open.