I often find myself making simple judgment errors during planning sessions for large projects. Agile teams consistently embark uprepared for high risk projects because they underestimate odds they will face. Kahneman’s Thinking Fast and Slow describes a common planning fallacy as “a lethargic unwillingness to think about what has happened during similar projects in the past”.
Executives are often delusionally optimistic about potential positive outcomes. While decisions should be made after rationally weighing gains, losses, and probabilities — an optimistic bias is a significant source of risk. Projects are rarely left unfinished, but they often run over budget or past expected deadlines. Challenges arise from these misaligned expectations and can be avoided by a collaborative, realistic planning session with teammembers.
Far too often I see teams that fail to anticipate potential difficulties while estimating projects. Story points by Scrum teams provide an arbitrary measurement of effort to implement functionality, but rarely factor in unknown-unknowns. Often these optimistic forecasts cater to key client stakeholders who would absolutely appreciate a realistic assessment of cost and benefits before approving proposals.
In order to prevent best-case scenario planning, remember to reference similar cases in the past. Planning fallacies appear across every industry and can be avoided by anchoring outcomes with baseline cases. We often forget the variable human element throughout the duration of projects. Life tends to unfold in unexpected ways. Throughout the course of any large, global project you should expect something to go wrong. Projects that span months will inevitably encompass vacations, illness, unforeseen accidents and an occasional emergency. It’s reasonable to build in time at the beginning of projects for these, because honestly these unexpected impediments regularly surface days before a demo or deadline.