This document discusses the importance of asking "why" when automating tests. It notes that while the focus is often on how to automate and what tools to use, asking why helps ensure the right tests are automated in the right way. Specifically, asking why helps manage expectations around automation, determine if a specific test is worth automating and if the method of automation is efficient. The document encourages collaboration between industry and academia by asking why each group does what it does. It concludes by asking the reader why they personally automate tests.