Your latest deployment is to a large, successful enterprise with a field of reliable, essential components of all vintages - as well as a sizable foothold in the cloud world. It’s a busy place, with demanding projects to implement alongside waves of transformations - agile, devops, cloud - all competing for people and time and resources. You’ve been tasked with evolving the monitoring estate, and you know the right thing to do is lead them into an observability transformation. Now, where do you start? This talk explores how to introduce observability to large enterprises with a deep stack of technologies reaching right back to the early days of digitisation. From convincing stakeholders, to deploying your first tools, to enabling engineers to make their components observable (and convincing them that it’s worthwhile!) - and, finally, going from project to "just the way it's done".