The lies we tell about deadlines

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Personally think deadlines are a decent — maybe even good — thing and generally a necessary evil for work to function. Problem is, in the hands of the wrong managers, they become a series of complete lies and horseshit. Let’s run down a few of the ways that might happen, shall we?

“This deadline is being watched very carefully by such-and-such key stakeholder.” This is typically a lie. It’s the same lie that companies tell themselves when they say “Our target on this content is the CEO level,” but now the lie is reflected internally. Key stakeholders do not care about the deadline of some social media campaign or website redesign. They care about deadlines related to financials. That’s about it. Usually if you hear this, it is a shitty manager attempting to use a vetted name to “motivate” you. The sheer fact that they think this tactic is motivation is why I can call them a shitty manager. You consistently need to remember this when you have a white-collar office job: no one at the top cares about 85% of what you do, and all those 14-hour days of toil you put in? You could be replaced in 1 hour and none of them would care either. Capitalism is a complete animal. You just need to navigate to your spot as best as possible. But when your manager keeps claiming so-and-so cares about some small project deadline, please first realize that statement is a lie.

“This deadline is completely intractable:” Most managers sadly operate from this spot. Deadlines should be relatively set to have merit, yes. But deadlines can’t be intractable. What needs to be intractable is the quality of the output. If you are 1 week late on something but it’s 4x better, most people would take that trade-off. Well, most logical and rational people. Managers, fearing a loss of control, would often probably want the shittier, earlier project.

“This deadline is [arbitrary date in the future]:” I cannot count how many bosses I’ve had or observed that do this. If a meeting is held on January 10th, they look at the ceiling and say “So, January 25th for these deliverables?” It’s OK to wait until after a discussion to set deadlines, because here’s what you need to take into account:

  • Competing projects
  • People’s schedules
  • Time off
  • What’s really a priority vs. what isn’t
  • General workflows

When dozens of managers in a company just arbitrarily assign deadlines, we just create this “Temple of Busy” nonsense where everyone is spinning 47 plates worth of deadlines, even though most of them are ultimately meaningless drivel. That leads to work stress, which leads to burnout, which leads to turnover, which is a cost. If managers just said “OK, I know the deliverables, let me think about the bigger picture and come up with some deadlines,” companies would save money. It’s that simple. Reaction instead of response.

“Well, this deadline has been mapped to the road map…” I’ve seen this at 3–4 jobs. It’s as if no one understands what a “map” is. A map shows different routes. If something changes, you can take a different route and still arrive. Companies seem to think “map” is a straight line from A to B with no other lines. I worked at a place once where some deadline was November 19th, right? (Before Thanksgiving, so I’m sure it’s going to be heavily reviewed.) Nothing that was supposed to come before was in place by November 19th, but we got hammered about that deadline. The deadline was sacred. The work would be garbage and lack numerous elements, but we had to hit 11/19. Does anyone understand how psychotic that is? You are just trying to check a box, not actually do productive work. Sadly, those are often the people who get promoted.

“You’ll work better with more deadlines:” Psychologically, most people don’t — and that’s even more true in an era where multiple bosses are common.

What else might you add on the pros, cons, and lies around deadlines?

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Blogging, largely about work and how to improve it. How I make (some) money:

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