Automation in testing is like a relationship in that there are many facets to it and it is complicated. This will become clear from a series of my experiences during my 20 years as a test automation architect and expert. Each experience will point out a number of topics to consider in a project, both things that went well and things that did not but all of them important. A comparison with human relationships will be made each time. In the end, we find a clear structure in all of it that helps ask the right questions in a project. As usual, it is a context that determines what the answers to the questions should be, but it starts with asking the right questions. The audience can take home this overview (also in the form of an ebook that will be ready then) and apply all of it immediately.