Most founders I talk to come to me with some version of the same question: How do I implement AI across my organization?
It sounds like the right question. It isn’t.
The right question is: How do I get my people aligned before I implement anything?
Those are not the same question, and confusing them is one of the most expensive mistakes a growing company can make right now.
Imagine a leader stands up in front of their team and says, “Follow me.”
But then someone asks, “Where are we going?”
And the honest answer is, “I’m not entirely sure.”
Then someone else asks, “How are we getting there?”
And the answer is, “We’ll figure out the vehicle on the way.”
That organization is not ready to implement AI. Without leadership alignment, any change — especially one as big as AI transformation — could be disastrous.
People need a shared foundation to anchor to when the change gets hard, when the new tool feels clunky, when the old way of doing things feels easier. Without a clear destination and a leader who can articulate why it matters, people will avoid, fight, and mistrust change.
This isn’t a theory. It’s a pattern I see consistently when I go into mid-size companies to assess their AI readiness.
The assessment results come back. The exposure scores are high. Shadow AI is already happening. There’s urgency, and it’s real. But underneath the AI readiness problem, there’s almost always a more fundamental one: leadership hasn’t defined where the company is going, what it stands for, or how decisions get made. Core values exist in someone’s head but haven’t been articulated or disseminated. The vision stops at “we want to grow.” There’s no operational roadmap — no three-year target, no one-year priorities, no 90-day focus.
You also can’t win your people over to a transformation they don’t believe in. If employees are already operating without a clear sense of shared direction or trust in where leadership is taking them, rolling out a major organizational change — and AI implementation is a major organizational change — doesn’t fix that problem. It exposes it.
Before I started working in AI, I was a Scaling Up coach, and the more I learn about AI implementation, the more I find myself leaning back into what Scaling Up taught me. Get the leadership team aligned on vision, values, and priorities first. Work backwards from a long-term goal to a 90-day plan everyone can execute against. Build the operating cadence that makes accountability possible. Then, and only then, do you start layering in tools and technology designed to scale what’s already working.
The same logic applies to AI. If you don’t have a roadmap for your operations, you can’t have a roadmap for your AI. If your people don’t know what they’re fighting for, they won’t fight for the new system. If your leadership team isn’t aligned on what’s acceptable in the business, they won’t be aligned on what’s acceptable with AI tools either.
This doesn’t mean AI has to wait forever. It means the sequence matters. Companies that skip the alignment step don’t just slow down their AI implementation — they spend money on pilots that stall, tools that go unused, and rollouts that generate resistance instead of results.
The question was never really about AI. It was always about whether the organization is ready to change. AI just makes the answer harder to ignore.
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If you’re a founder or executive trying to figure out where to start with AI, I offer a complimentary AI Readiness Assessment. We’ll look at where your organization actually stands — not just the technology, but the leadership foundation underneath it. If there’s work to do before you implement, you’ll know exactly what it is.