We are all working to deadlines, all the time. Whether you’re working to a daily print deadline or a project deadline further in the future, everbody is ruled by the deadline. Too often we don’t get to choose our deadlines, they get imposed upon us. Our workload is also something we can’t always control. This means we are often looking at calendars knowing that work left to do is impossible to be delivered by the deadline.

Understanding your deadlines is key to organising your work.

Don’t make up deadlines

David Allen in his Getting Things Done book says don’t add a task with a due date if it’s not a “real” deadline.

Resist this impulse. You need to trust your calendar as sacred territory, reflecting the exact hard edges commitments.

In a professional environment work often comes with an expected deadline. If we don’t have control over our assigned work then unexpected work can put old deadlines in jeopardy. At this point, some deadlines will have to be moved. But if the deadline can be moved, was it ever really a deadline?

This suggests that there is more than one type of deadline.

Motivational deadlines

David Motto helpfully suggested a method of using deadlines to improve motivation. He outlined 3 levels of deadline for musicians to encourage practice and preparation.

  • Type 1: Outside of your control and accountable to others e.g. an audition or performance with a paying audience
  • Type 2: Inside your control and accountable to others e.g. setting a date for a rehearsal performance with family and friends
  • Type 3: Inside your control and accountable to yourself e.g. perform a mock concert with no audience

His definition works well in this context of motivation. However, it didn’t help to distinguish between external deadlines that can be moved.

Type 3 is clearly not the type of “real” deadline we are looking for. The article suggests that this is the hardest deadline to meet and requires a lot of motivation. I could simply choose to do my mock concert with no audience a day or two later.

Type 2 looks like a real deadline… but who are you performing to and how accountable will they make you? If I was performing to friends and family, any mistakes would certainly be forgiven, especially as it wasn’t the “real” event. In software development you can demo work to others but if it’s not quite right, is there enough accountability to not gloss over imperfections? The criteria for a successful demo is that it looks good, it does not necessarily have to BE good. This potential loophole in meeting a deadline doesn’t feel like it’s “real”. This suggests that the event has to be “real” as well as the date.

Type 1 in this context fits my idea of a “real” deadline. There’s a performance and that can’t be moved. In the world of software though we see many deadlines often linked to arbitrary events e.g. the end of a company’s financial year. Those deadlines can and do get moved because it’s better to improve or finish the work than it is to reach that exact deadline. This is only often discussed with any real meaning very close to the original deadline.

Prioritising deadlines

When you’re overwhelmed with deadlines you need to know which ones are “real”. I found myself in this position a few years ago. Commitments had been made and were only communicated with the team when time was running out.

We put all the tasks on a board and tried to set a priority order. We started by ordering them by date but discovered that the competing deadlines were impossible to meet. We started to question the reason for the work and quickly realised that not all the deadlines were “real”! Some were arbitrary, some were important and others had contractual implications.

We started to form our own version of the 3 deadlines:

  • Real deadline: Chosen because it was contractual or facilitated other commitments
  • Expected deadline: Chosen because it made scheduling resources simpler
  • Target deadline: Chosen because it allowed new work to be added or for the internal sales team to demo

This allowed us to prioritise which deadlines were more important. As we went through the backlog it got harder for the work to fit neatly into 3 types. We needed to understand what we meant by deadlines even more.

Accountability

Whereas David Motto’s deadlines focussed around accountability, our deadline’s centred on flexibility. We had found the concept that helped determine the “real”-ness of a deadline - the ability for it to move. This by itself though didn’t help to categorise our deadlines.

Earlier we discussed how an event had to be “real” and that a concert for friends and family could be too forgiving to be taken seriously. Imagine instead, the example of a grand performance. The venue that had been booked and paid for, a long marketing campaign may have been run, many shift staff who were relying on the work and hundreds of ticket buyers who had paid for baby-sitters. The inconvenience of missing this deadline is much greater and the public would be far less forgiving. There are severe consequences to missing that deadline.

This gives us a second lens in which to view deadlines. Flexibility and consequences.

Consequential deadlines

If flexibility defines the type of deadline we are looking at, then consequences helps us to define that flexibility. As shown in the graph below they are inversly linked.

A new Automator application interface

This means we can establish the 1st law of deadlines:

The more severe the consequences, the more fixed the deadline will be.

This law makes it trickier to define the moment when a deadline becomes real. The graph shows a line which marks the point where a deadline becomes real. There is no formula for how to decide where this line should be but I have established a helpful maxim:

A real deadline is one where the consequences are too great to be missed.

Other thoughts I’ve had during writing this which I may write about further if there is interest:

  • How to set deadlines for “real” events that aren’t scheduled e.g. disaster planning
  • Mapping whether a deadline’s consequence rises or falls over times