Doing our best work often means pushing past what is familiar, safe and comfortable. This is particularly true when the work we are doing is complex and uncertain, where we face many options but no obvious choices, and when each decision introduces new complexities and consequences. There is no clear plan, no well-defined path and few easy answers. Leaving our comfort zone and building good solutions to challenging problems means we still need some means of navigating and course correcting. The form that takes requires answering some different and difficult but absolutely essential questions.
I have always taught that a central principle of managing projects is that you should have a clear picture of what “done” and “done well” look like. That’s easy to define when something is straightforward and clear. It becomes much more complicated when we start straying into the realm of creativity, and of doing work that is complex, messy and uncertain. When we have many choices and options of how we might proceed, and those choices lead exponentially to other implications and impacts, it can be hard to know how to proceed, where to look or where the finish line is. The good news is that there are some thing to look for that can help.