The problems remain the same. Legacy systems. Disengaged employees. Defects all around. Long delays getting software released. Being left behind by the competition. But why does everyone run into the same problems? And can they get out? They say the first rule of holes is to stop digging. There’s a reason we start digging in the first place. We thought it would get us closer to where we needed to be. It just happened to get us stuck at the bottom with very few options of escape. This talk is all about unintended consequences. The dysfunctional situations we encounter are created because well intentioned actions, intended to fix real problems, have only caused more and deeper problems. We simply didn’t foresee the wider impact. We can take a page from systems thinking, but how do you know what to look out for? I’ll use familiar, concrete examples, to show what type of impact to look out for and how to see if you are just doing local optimizations. I’ll also provide a simple and quick checklist to help avoid overlooking undesirable impacts. After all, when we know where the holes are dug, we can avoid falling into them.