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Don't Shoot The Deadline


People hate deadlines. They cause stress and encourage people to work long hours. There are three basic types of deadlines:


  1. Those imposed by internal people or factors

  2. Those imposed by external stakeholders

  3. Those imposed by “the system”


Working backwards, by “the system,” I mean institutions that are bigger than one or a few people. A good example of this would be tax day. Every year, somewhere around April 15th in the U.S., accountants are wrapping up a frenzied period of doing tax preparation. It is estimated that they do about a third of their annual billing in this period, working an average of 55 hours per week. In talking with a few of the accountants I know, it can be a lot more than this. Deadlines like this can’t be moved, but they are usually predictable well in advance, so preparations can be enhanced over time.


The second type of deadline is one that is handed to you by an external stakeholder -- often a customer. The customer may be handing you a type #3 deadline that they have, or they could be handing you a type #1 deadline that they made up. An example of the former might be a big trade show for which you are helping them prepare. While type #3 deadlines are non-negotiable, the #1 type are -- even if they claim they aren’t. You just need to be negotiating with the right people.


Which brings us to the infamous type #1 deadline -- the most common of all. We tend to hate these deadlines the most because their motivations are often tainted. They could be tainted by the ego-driven ambitions of an upwardly mobile leader. They could be tainted by the bad decision-making of someone in a position to make commitments on behalf of others in the organization. They could even be tainted by a misguided plan to “energize” and “motivate” the operational workforce.


Here’s the thing: deadlines are actually a good idea. They’re very helpful in situations in which coordination across teams is necessary. They also provide a valuable sign-post as to whether the work is on an expected trajectory. There are actually lots of good things about deadlines including their potential to provide motivation. So, why do we hate them?


The answer, my dear Watson, is simple. The wrong people are setting them. Type #1 deadlines should ALWAYS be set by the people committing to the work. Furthermore, these types of deadlines should be subject to change without notice if and when the proverbial unknown unknowns rear their ugly heads. To be fair, good teams should include a reasonable amount of padding for these in the initial estimates that lead to the setting of a deadline. I’ll talk more about estimating in a future article. Suffice it to say for now, if your estimates keep coming up short, keep upping your padding until that stops. I had a friend once who said that when a rookie developer gave him an estimate, he would double it and add a zero before passing it onto the client. That system worked pretty well for him.


Sometimes, the surprises that inevitably show up during product development are far too big to absorb into your initial estimate. My advice here is -- DON’T WAIT! Tell everyone early and often as soon as you know. Make clear that the original deadline is blown and needs to be moved. If other teams need to react to this change, make sure they have the longest runway possible to make adjustments to their interconnected plans.


If you get pushback, be prepared with scope changes that could keep you on track. Nobody likes the idea of scaling back the value that you planned to deliver, but it’s the only other lever the team can pull. Putting in a bit of extra work now and then isn’t unreasonable, but there’s a reason one of the 12 agile principles speaks directly to the concept of sustainable effort. Falling back on pushing the team every time something derails a deadline is a crutch that ultimately leads to a whole different injury (high turnover). If you’re thinking about shifting resources to move things along faster, consider this only if you have people that are knowledgeable enough to hit the ground running. If they can’t do this and you’re still thinking about it, you haven’t read The Mythical Man-Month yet (written before gender bias was considered as part of book titling)


So, next time you get handed a deadline, don’t shoot the deadline -- shoot the messenger. Then, maybe you’ll need to shoot the deadline, too, but let the team examine it first. Who knows, maybe whoever came up with it is better at estimating that you. It’s unlikely, but stranger things have happened.


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