Whether on a personal or a project level, the calendar is the most important measuring stick used to gauge progress because it is the measure everyone understands and can follow. We mark significant milestones with a celebration. For example, birthdays are always milestones and every country, person or project has a birthday (whether they celebrate them or not is another story). Whether the celebration is annually or monthly (anyone with a newborn has celebrated birthdays monthly), isn’t as material as using the calendar milestone to create space for celebration and reflection. Recently my wife retired after a long and fabulous professional career. This is a milestone event in her life and time to reflect on where we started, our character, and the path we intend to take forward.

All project management techniques include time for reflecting on how to improve. In Agile, we build in time for reflection called retrospectives. While in classic waterfall projects, we have post-implementation reviews. What is rarer is personal reflection. Sure we create resolutions on New Year’s Day, but how often do we review our progress against those goals? Milestones represent a chance not only to celebrate, but, as importantly, time to step back and introspect. For example, the team at the Software Process and Measurement Podcast and blog (yes there is a team) spent a bit of time during a recent retreat reflecting on some stalled projects and how we were going to get them going.

Milestones evoke celebration and introspection. Celebration is the easy part, what is typically harder is to reflect on how we met our goals. In some cases, we accept accomplishment by asking whether means justify the ends. Early in my career, I saw projects that, even though they delivered great outcomes, left project teams in shambles, or in some cases, used creative accounting to hide budget overages. In the short run the celebration was exciting, however in the long run was cost worth the benefit? I think not. Tellingly, I do not know anyone from that stage of my career who is still in the business. A better approach is when the markers that show that time is passing are a signal to celebrate and find time to reflect and renew. In projects, those milestones include sprint reviews, demonstrations, sprint planning or classic phase gates. Each of those milestones generates feedback that helps teams and individuals change direction if needed. Feedback provides the impetus for change. It is usually easy to mark those events by letting friends, family, and stakeholders know what has been accomplished since the last milestone.

Everyone likes a celebration, whether they includes fireworks, a piece of cake, a gold watch, or the demonstration of some tasty bit of promised functionality. After the hoopla dies down, step back and reflect on the path that has been taken. Seek out feedback, just like a retrospective, and make changes where needed to ensure that at the next milestone, you do not have to think about what you should have done.