Building a strategic roadmap feels good. You get the team in a room, you listen, you collaborate, and you land on something real — a mission, a set of priorities, a shared sense of what “at our best” looks like. That part is worth celebrating. Then it gets hard.

Amy Richman has done this at Microsoft, Starbucks, and now CVS Health. Once the roadmap exists, everything has to be held up against it — operating model, tools, processes, team behaviors. Her question is simple: if it doesn’t map to the vision, why are we still doing it? Answering that question requires real change. Teams resist. Fear shows up. The change management required to bring people with you is massive. Amy learned this the hard way, and she’s here to share what that actually looks like.

Amy walks through the whole thing — why she builds roadmaps collaboratively, how strategy connects to operating model, and what leading a team through the change that follows actually costs. She’s living it right now at CVS Health. This is a working case study, not a retrospective.

Attendee Takeaways

The “at our best” exercise. A specific facilitation tool Amy uses to get teams to agree on how they want to behave together — before the hard work starts. It sounds soft. It isn’t. Done right, it becomes the thing the team points to when things get uncomfortable.
How to run an operating model audit. A practical method for reviewing tools, processes, and team structures against the strategic vision — and making deliberate decisions about what stays, what changes, and what gets cut. The audit is where the roadmap becomes real.
What to do when the team is in a fear state. Change triggers fear. People stop taking risks, start protecting turf, and wait to see what happens. Amy shares specific signals to watch for and how she redirects that energy — from defensive to engaged — without glossing over the discomfort.
The “sprinkling vs. dumping” test. Every leader brings a playbook. The failure mode is dropping it wholesale on a new organization and expecting it to stick. Amy’s framework for knowing when to carry something forward, when to adapt it, and when to leave it behind — based on 25 years of making exactly that call across very different businesses.