The idea for this article arose during a meeting where we learned that our supervisor would be leaving the company to pursue new opportunities. In response, a colleague lamented that what we would miss most is the knowledge departing with the leader. Unfortunately, that’s how it goes. Not only do we lose a colleague, but we also lose valuable knowledge and experience. However, this isn’t a story about my supervisor; it’s a story about all those individuals who are experts in their fields, who understand the paths to success and paths that lead to catastrophic failures. When they leave, they take with them knowledge that you won’t find in any book, note, or Jira ticket. And this leads to a fundamental question: What can be done to avoid this “black hole” of knowledge? How can we ensure it doesn’t vanish along with them? That’s what this article is all about.