Most business leaders talk about AI adoption, but Alane Boyd and Micah Johnson are asking a sharper question: how do you actually measure it? In this episode, they introduce a concrete five-milestone framework for tracking individual AI fluency on your team, built from a real gap they identified at a recent COO conference where everyone agreed the topic mattered but nobody had answers.
If AI adoption at your company feels more like chaos than progress, there's a good chance your team has no shared baseline — and no way to know who's moving forward and who's stuck. Alane and Micah make the case that undefined fluency goals are a business problem, not a personal one, and that the fix is simpler than most leaders think.
In this episode, you'll learn:
- How to define milestone one so every team member has a clear, achievable starting point with Cowork
- Why Skills, Folders, and Connectors mark the jump to milestone two, and why that baseline alone drives major efficiency gains
- What human-in-the-loop design looks like when someone reaches milestone four and starts building AI workflows with built-in approval checkpoints
- Why milestone five isn't for everyone — and how chasing it too early can actually slow down your results
- How one team member spent 5 minutes building a Skill that now saves 45 minutes every single day
- The two-track model — individual vs. organizational, and why both need to be measured to see real AI success
If you're ready to stop guessing about where your team stands with AI and start building a measurable path forward, this episode gives you the exact framework to do it, press play now.