Tight deadlines? You’ve got a crappy manager.

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Tight deadlines are a very common thing (concept?) in business. We’ll address the ‘why’ of that statement in a few moments, but almost regardless of job/role, you’ve probably experienced some tight deadlines. Oftentimes this causes people to shriek, run away, and hide under their desk. (The other reaction is to tell everyone how busy they are constantly.) In short, we all have a fraught relationship with deadlines, and especially tight deadlines. But why is this? And what can we do to make it better?

Tight deadlines: A few initial points

First off, tight deadlines are not necessarily bad things. Most companies are very bad at priority management, and tight deadlines can drive people towards achieving the right things at the right times. (This doesn’t often happen, but it could!) There’s a documented dark side to tight deadlines, too: they can wreak havoc on your health. There’s also a much broader, more philosophical discussion here about ‘moving fast vs. moving smart.’ Some companies, and their senior leaders, think it’s all about first-mover advantage and hitting targets ASAP. Others think it’s about smart plays. It kinda varies by who you work for. Deadlines, and the potential for procrastination, play into that. The final point to consider before we dive deeper? Maximizers vs. satisficers. The former type of boss is basically a perfectionist. Nothing can ‘get out the door’ unless it’s superb and ideal. The latter type of boss is willing to release a good product/service, have people deal with it, and make adjustments. Both kinds of bosses have pros and cons.

Tight deadlines: Sense of urgency, lack of priority

This is where a lot of people begin to be frustrated by tight deadlines, I think. Follow the bouncing ball.

  • Most people tend to fear/respect hierarchy (i.e. their boss), even if that respect isn’t necessarily well-deserved.
  • As a result, what your boss says is important.
  • The problem, as noted above, is that many organizations are not great at setting priorities.
  • When you get down to the middle management level, there’s often almost no connection between what’s being assigned and the CEO’s priorities.
  • But because those middle managers need to seem relevant to their bosses, they want to be seen as “go-getters” and “producers.”
  • As a result, every project they assign you has a “sense of urgency” attached to it.
  • You now have 10 projects, with 10 tight deadlines, and you want to go plunge your head in the toilet.

This is the psychological vortex that is work for many people. In short: executives chase money and very little else matters. But to get the money, a variety of day-to-day tasks have to happen. Most executives couldn’t care less. Their priority is “get the money” or “get the growth.” So all these other people, with direct reports, have to do … uh … something? They oftentimes straight-up create work, as if from whole cloth, and then deem it “urgent.”

Dirty little secret: if 10 things are urgent, nothing is urgent. The definition of “urgent” is pretty accepted by 2016. 10 things can’t be concurrently urgent; it’s a violation of the term.

These bullets above create the ‘tight deadlines’ issue for many people.

Tight deadlines: So, what do we do?

It’s hard, but I’d make a few arguments here.

Better Priority Management: This is like telling some execs to walk on water, but it’s important. Define what needs to be worked on, and in what order. Cascade that down. Stop adjusting workflow every 30 hours for a new shiny penny. It doesn’t help anyone.

More organic management: A lot of people only ‘see’ their boss via email or rushing past them in a hallway (“Late to my 12:15!”). That’s bad. It’s really bad, actually, and it’s not leadership. Hell, it’s barely even ‘management.’ If managers came over and talked to their direct reports and explained what a project was, who was involved, who needed it, why, when, etc … that’s better. And that reduces tight deadlines because people now understand “OK, this is more important than this.”

Workflow tools: I don’t think you can solve people issues — bad communication — with software, but you can use something like Basecamp to see what people have on their plate. This terrifies most people because secretly we all want to surf the Internet all day and not get assigned new work, but … the company’s paying you, so go do something once in a while. Transparency about workflow is actually crucial if you truly believe that everyone is so busy and your entire team is understaffed.

Cower under our desks and weep: A fourth option on tight deadlines is always appreciated, yea?

The tight deadlines-criticism matrix

This is always amazing to me — and no one discusses it. Here’s what I mean.

At every job, there has to be some degree of criticism baked into the culture. You can’t just send documents around and have everything approved the first time. What would be the role of managers? Of gate-keepers? There always need to be iterations, adjustments, and tweaks. That’s kinda how work, well, works.

But this is what happens with tight deadlines a lot: someone will set an “out-there” deadline, i.e. “This project is completely due in six weeks.” Got it?

In the first three weeks of the six weeks, every line-item and document will be edited 19–25 times, with 28–32 new people requesting access. It’s a confusing mess of version control. In sum, it’s typically reams and reams of bullshit.

So now you’re halfway to the six weeks, and all you’ve done is edit a bunch of documents 32 times. Now people get nervous. Tight deadlines a-comin, boy! We got targets to hit!

Still, people spend another week sending emails back and forth like “Re:re:re:re:re:re:re:FWD:re:re:re:FWD:re not sure of Version 12 edits…”

Now we’re at four weeks. What happens? Tight deadlines bearing down, so now everyone rushes to approve everything as quickly as possible. “We gotta get it out the door, boys!”

This is a horribly ineffective approach to creating something, and yet, I’ve been in this exact situation 21,933 times. (Scientific estimate.) The tight deadlines result because everyone spends the first 66 percent of a project trying to justify their worth to the project — as opposed to making the project the best it can be. I just explained work in like, 2 sentences. Where’s my prize?

Tight deadlines and generic convos

Final point here. Every personality test or productivity study always has some matrix about deadlines and procrastination. People get their results back from some overpaid consultant, and for 2–3 days all they discuss is “Well, Jenny, I’m just such a procrastinator!” It always makes me want to self-immolate. Procrastination is not a fixed character trait; people procrastinate on projects they don’t give a crap about or see no purpose in. When they care, they’re off to the races. It’s pretty simple, basic psychology that no executive ever seems to understand as they race to analyze Q2 ROE.

Look, here’s the deal. How you deal with tight deadlines certainly says something about you in a work context, but how these tight deadlines tend to come about? It says a lot more about where you work and how it could improve. And heck, maybe with a little sense of urgency, right?

Your take on tight deadlines?

My name’s Ted Bauer. Here’s my blog. Here’s my newsletter. Let’s connect, eh?

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Blogging, largely about work and how to improve it. How I make (some) money: http://thecontextofthings.com/hire-freelance-writer-ted-bauer/

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