How do you measure whether a transformation initiative is succeeding?

Situation: We launched an "engineering excellence" initiative—shifting from hero-based deployments to a platform model with self-service CI/CD, standardized observability, and shared libraries. The investment was significant: six engineers for a year, plus training and tooling. Leadership wanted to know if it was working.

Task: I owned defining success metrics and tracking progress. I had to move beyond "we shipped the platform" to outcomes that mattered to the business and the team.

Action: Before we started, I worked with stakeholders to define success criteria. We agreed on: (1) 80% of teams using the new platform within 12 months, (2) mean time to deploy reduced by 50%, (3) production incidents caused by deployment issues down 40%, and (4) engineer satisfaction with tooling above 4.0. I set up leading indicators—weekly adoption rate, deployment frequency per team—and lagging indicators—incident count, satisfaction survey. I created a simple dashboard and reviewed it in our weekly transformation sync. We also ran bi-weekly "pulse" surveys: "How confident are you in our new deployment process?" When adoption stalled at 60% in month eight, we dug into qualitative feedback: teams said onboarding was confusing. We added documentation and office hours; adoption reached 85% by month 14. I reported monthly to leadership with the numbers and narrative.

Result: We hit three of four targets: 85% adoption, 55% reduction in deploy time, 45% fewer deployment-related incidents. Satisfaction landed at 3.8—close but we kept iterating. Leadership extended funding for year two. I learned that defining metrics upfront forces clarity, and mixing quantitative and qualitative data catches what numbers miss.