It’s hard to talk about deadlines in isolation, deadlines are a part of a larger system of goal setting: time, teams, objectives and results.
Over time my view on the subject of deadlines has evolved and I am certain that a part of this article is going to be a shock to some people who worked with me several years ago. I was an early adopter of Scrum in 2001 and loved sprints with estimates for a long time, but in the last couple of years I have stepped away from Scrum because I realized that Scrum fails to distinguish important vs unimportant tasks and activities.
If you focus on too many things at once, by definition you are not focused. If you estimate every task and make sure that every 1-3 days there is a mini deadline, you start to miss the forest behind the trees. The burn down chart becomes the goal and the actual goal takes a back seat. People start feeling like they are hamster in a hamster wheel running somewhere and being stressed out for an uncertain cause.
One of the groundbreaking books I have read on the subject of goal setting is “Measure What Matters”. A quote that stands out from the book is: “When people have conflicting priorities or unclear, meaningless, or arbitrarily shifting goals, they become frustrated, cynical, and demotivated.”
I would add to that quote by saying that if you have too many small goals it fails to inspire longer term thinking and bring people together. In short: while decomposing a task into components helps you understand it better, driving for everyone one of those to be estimated and done on time wastes precious management ammo.
Deadlines are a source of stress, but they can also be a source of pride and celebration. When deadlines are put in a meaningful context, which 1-3 day stories rarely can be, the team rallies to achieve them and the company should celebrate those wins. If the goals are not meaningful enough to recognize and celebrate were they important enough to stress about?
Doerr, John. Measure What Matters: How Google, Bono, and the Gates Foundation Rock the World with OKRs. Penguin Publishing Group. Kindle Edition.