Scott Belsky says there are really three types of deadlines:
1. Data-Driven Deadlines: You break an entire project down into concrete steps, each with a specified amount of time it takes to be completed. And then, when you add up the time for all of the steps, you get an estimate of time required for the project. After taking into account the number of people working on the project, you get an actual target date for completion – otherwise known as a deadline. Of course, if you miscalculated – or altogether miss – a step in the process, then you will miss your deadline. Upon reflection, you will learn why you underestimated the steps. And such knowledge, while painful to learn the hard way, will be valuable in future project planning.
2. Arbitrary Deadlines: You put your finger in the wind and attempt to feel, based on past experience or a wild guess, when something will be done. Or, you pick an upcoming event and arbitrarily make it a deadline. Often times, this practice has the sole purpose of just having a milestone in mind. Common in start-ups or in projects with client-imposed deadlines, you are relying on a lot of luck and hustle. An arbitrary deadline is certainly better than no deadline. No doubt, the mental benefits of a deadline are helpful in pacing the project. Arbitrary deadlines are most effective in an iterative project planning process. You must consistently reassess the deadline as more information reveals itself. Ideally, arbitrary deadlines evolve into data-driven deadlines as more information reveals itself.
3. Bureaucratic (Padded) Deadlines: When you’re tasked with creating a deadline and reporting it to the higher ups, you have incentive to “pad” the deadline with extra pockets of time. While it helps to manage expectations and protect your reputation, the practice of padding deadlines will compromise the learning. The causes of miscalculated projects and missed steps may pass unnoticed because of the margin of error providing by the padding. While the higher-ups may be pleased, in actuality your team is robbed of valuable learning.