Essentially, observability is a collection of approaches and best practices that allow us to look into a running software system, and understand how it behaves, how it misbehaves and what’s broken inside. While the idea is brilliant and perfectly works in teams that own software systems end-to-end, enterprises face a set of unique challenges that can drive observability useless if not properly addressed. In this talk, I will explain these challenges and how they can be solved before turning into unsolvable problems. We will look into technical, organizational, processual and political aspects – all these are unavoidable when applying such a change to an enterprise. The listener will learn what to look for in order to apply observability ideas in their enterprise without risk of failure, and hopefully get excited about possibilities and chances that come with the introduction of observability in their enterprise.