Company-wide AI Implementation in Five Steps
Mauricio Cavallini 6 days ago
Typo?
Company-wide AI Implementation in Five Steps A look inside Every’s executive training playbook
June 1, 2026 · Updated June 3, 2026
Listen Listen Copy Link Share on X Share on LinkedIn Share on Facebook Like 6 Comments Join me and Dan Shipper for a live session on what AI fluency looks like at the executive level tomorrow, Tuesday, June 2. We’ll walk through how the leaders we work with—at hedge funds, private equity firms, and Fortune 500 companies—are using AI in their day-to-day, and what they wish they’d done differently six months in. RSVP.
Sitting across from the chief operating officer of a health tech company earlier this year, I watched her name a problem many executives are feeling but few say out loud.
“Our junior employees are probably much more native with this technology,” she said. “And we need to make sure we’re sticking with it. Makes me feel like a dinosaur to say that, but it’s true.”
Confessions like this come up regularly during our executive training sessions: Leaders aren’t working directly with AI on sophisticated tasks, even as they’re guiding planning decisions about the technology. They know they should spend more time learning the tools, but they haven’t committed to it yet. That’s understandable; executives are incredibly busy. But what we see in our sessions is that leaders who haven’t gotten their hands dirty don’t clearly understand the practical opportunities and challenges of AI. That health tech executive’s admission sparked an important conversation about how a coordinated company-wide approach to AI implementation starts with executive AI fluency—but doesn’t stop there.
We see this pattern in every engagement we run in our consulting work. Over the past two years, we’ve trained thousands of people at companies including the New York Times, Ripple, Headway, and Thumbtack, and at investment firms managing over $100 billion in assets. We’ve done the workshops and watched what changed six months later.
AI usage in the workplace is now widespread, but it’s an altogether different ballgame to build organizational capability that truly realizes financial gains.
McKinsey defines AI high performers as organizations that report both significant value from AI and more than a 5 percent impact on earnings before interest and taxes (EBIT). These companies are nearly three times as likely as others to have fundamentally redesigned their workflows, but they remain a minority: Only 6 percent of the nearly 2,000 organizations surveyed met the criteria for success.
As AI has gone from performing party tricks to completing an entire day’s worth of human work in three short years
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