Given that coordination and communication swamp all other costs in modern software development it is a pressing area to invest in, especially as your team scales. I use a framework of a Small Number of Well Known Tools to build shared understanding in our complex systems over time. When we want to do something other than use the Small Number of Well Known Tools (in the small number of well known patterns), that’s a Departure. I have a long note I want to post on technical decision making and departures. In the mean time I want to share a short list of questions I’ve been using in various forms for over a decade to engage with The Dreaded Question.