Why Deadlines? Why That Deadline?

It was about 10PM that Thursday night when I got back to my apartment. After a full day of work, I’d helped haul a bunch of sound equipment, set it up, run sound, hauled the equipment back, and spent some time unwinding with friends.¹ I was tired.

The light on my answering machine was blinking.²

“You have one new message. Message one. Hi Matt, this is Barry³ from work. Hey, we need to make some changes to the track data⁴ before the release tomorrow morning…”

So I headed back to work to make the changes. I recall there being only a few, but the tools at the time were really primitive, and I don’t think we’d built any error-checking tools yet. I knew I was tired and likely to make mistakes. So I manually triple-checked everything, loaded things up in our train simulator, ran over the affected track, and everything seemed good. I published the changes, emailed everyone, and headed home sometime after midnight.

The next morning, I got to work⁵ and discovered the release had been postponed.

The urgent deadline Barry had relayed to me—and to be clear, he wasn’t the source of the deadline—had gotten pushed back a week or two. The results of those few hours of late-night-early-morning work would still be needed, but could have been done in an hour of well-rested work.

I share this story because I’m absolutely certain that this is the only time a deadline has ever been pushed back…wait. I’m now being told that’s not the case, and bogus, shifting, or unreasonable deadlines are common. Who knew?

Let’s talk about deadlines.⁶

Why Are Deadlines Assigned?

Horstman’s Law of Project Management is “who does what by when“. And studies have shown that deadlines often drive behavior.

Let’s get a little more granular than “deadlines are for project management and changing behavior”, shall we? Managers assign deadlines for lots of reasons:

• To coordinate work
• To show dependencies between tasks
• As an objective way of measuring progress toward a bigger goal or deadline
• Because Microsoft Project auto-calculated due dates based on estimates
• To keep people working together toward a common goal
• To make expectations clear (e.g., in a contract)
• To show priority
• To make a person or team focus
• To create a sense of urgency or value of time
• To show that a team is succeeding—or failing
• To represent a real-world event⁷ or consequence, like a trade show or a promised ship date⁸
• To represent an “appetite” for work (e.g., I want it, but it’s only worth a week’s effort)
• To give guidelines for investment
• As punishment
• To make a manager seem “tough” or “on top of things”
• To show that someone else’s team is the “weak link” or “long pole”
• To estimate completion dates or work sequencing for a larger effort

There are others, but I’ll stop there. That’s already a lot of reasons for a deadline.

I won’t even get judgy about which of those are “good” or “bad” reasons for assigning deadlines. There are one or two that I’d consider almost-always bad, and several that are probably almost always good. But even for those, I could think of exceptions.

With so many reasons for a deadline, what does it mean when you assign a deadline? They are, as you can see from the size of that list, a very blunt tool.

Are you clear in your own mind what this deadline means?

Are the people that will be executing on the task clear what this deadline means?

Know—and Communicate—Your Reasons!

Deadlines drive behavior.

Confusion about what kind of deadline you’re dealing with can drive confusing behaviors.

“Please email me the report by 2PM on Tuesday” could mean “I’d like the report so I can check it off on the project plan at the next status meeting.” Or it could mean “I need to absorb the report so when the exec team grills me about the outage first thing Wednesday I’ll be prepared and we won’t all get fired.” I’m sure you can imagine how things could go wrong if employee and manager had different ideas about what that deadline meant.⁹

Here’s the point: communicate the reason for a deadline.

If you’re assigning deadlines, tell people what the deadline means and why it’s important. “This is our top priority” or “we won’t be able to deflect the asteroid if we aren’t done by noon tomorrow” or “gosh it’d be nice to have this done but don’t spend too much time on it” all mean different things.

If you’re working a task that has a deadline, ask about the reason for a deadline.

Most people do better work if they have context, and the reason for a deadline is important context.

Now, if you’re not sure why you’re giving a deadline, consider whether there are other tools to accomplish whatever it is you’re after. “There’s no deadline on this, but we need it done so we can start the CEO’s new pet project” creates urgency without a deadline, and invites problem-solving. “No due date, but please don’t spend more than eight hours on it over the next two weeks” sets appetite and expiration without creating unwarranted urgency. A burn-down chart, a hill chart, color-coded work breakdown structure diagram, or one of those giant fundraising thermometers can show progress toward an overall goal. It’s okay to use other tools, especially if they fit the job better.

Deadlines are a powerful project management (and people management) tool, but they can’t be your only tool.

If you’re a people manager, remember that managers are communicated through. Sharing the reason for deadlines is a good example of “communicated through”.

Shape Up: An Example of Deadline Clarity

One of the things I really like about the Shape Up approach is that the six-week cycles are deadlines designed to communicate appetite.

The team doing the work knows the company has the appetite to fund the project for six weeks. Because that is clear, the team can flex the scope of what they build to fit that appetite.

There is no confusion about the reason for the deadline: it’s the end of appetite-budget timebox. It’s entirely arbitrary, but arbitrary in a way that creates predictability. No punishment, (generally) no real-world events attached, no dependency-management. It’s appetite.

I like that clarity.

I bet the people who work on your tasks also appreciate clarity. Just sayin’.

Wrapping Up

Deadlines drive behavior.

To drive the behavior that you want, be clear about the reason for a deadline.

And consider occasionally reaching for tools other than deadlines.

You’ll get better results, better outcomes, including a happier team.

And results matter!

If you’re not sure how to put this into practice, you need to book a coaching intro session by Friday at 5PM. Why that deadline? To make sure you get it done, and remind you of the urgency of learning to handle deadlines well.

1. It could have been at Perkins. Or maybe that day we went to Anti-Perkins, as we called Happy Chef for nerdy reasons. [↩]
2. This was long enough ago that not everyone carried a cell phone. An “answering machine” was a device that plugged into a home phone or “land line”, so when you weren’t at home to hear the phone ring, people could leave you messages. Like voicemail, but it lived in a box in your house. Mine was fancy and digital, though some used mini cassette tapes. Kids, ask your grandparents. [↩]
3. To be clear, not the same Barry as in The One Hour Employee. In this case, unusually, I’m using the actual first name of my former coworker. [↩]
4. At the time, I was the guy able to create track data for what became the standard North American “Interoperable Electronic Train Management System” solution for Positive Train Control. But that was more than 20 years ago, and there are much better tools now that run places other than my desktop computer. But I’ll stop before I write a whole PTC or track data blog post in this footnote. [↩]
5. A bit later than my usual 7:30AM. [↩]
6. The origin of the word “deadline” comes from a line at a US Civil War military prison. If prisoners crossed it, they’d be shot dead. Literal line, literal death. Fortunately, in office jobs, that tends not to be the case. [↩]
7. You’re making a Super Bowl commercial? You should have that done before the big game, not after! [↩]
8. If the asteroid is going to hit Earth in six months, the asteroid-deflection project darn well better be ready in six months or less. It does no good if it’s delivered after the asteroid hits. [↩]
9. In any combination! If the employee misinterprets it as an “unimportant” deadline and gets caught up in other work, the manager will have trouble at the grilling. If the employee misinterprets it as a “super-urgent” deadline and ignores other, actually-more-urgent work, that could create big problems for the team. [↩]