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The elephant in the room: let’s talk deadlines

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Hi! Today I want to talk with you about deadlines. In fact, I want to show you why I think it makes s
 

Work in Progress

October 28 · Issue #6 · View online
The newsletter about work

Hi!
Today I want to talk with you about deadlines.
In fact, I want to show you why I think it makes sense to give ourselves more deadlines.

Lots of people groan at the word deadline, often due to the annoying experience of having missed one. With all that entails, you can develop an aversion to anything remotely resembling a deadline.
And that’s a shame, because then you also miss out on the many benefits deadlines offer. Why else would you prioritize work that’s important to you, but not at all urgent, for instance, over all those pressing emails from people waiting on an answer?
Take a look at this diagram:
These three factors play a role when scheduling a project: What exactly is the scope of the job? How much time is available to do it? And what resources can be used?
Let’s go ahead and leave human resources out of it for now, because for our own work, that’s generally limited to ourselves. We’re now left with two dials we can adjust: the precise job at hand and the amount of time available to complete it.
If you make firm agreements about both factors, you don’t leave yourself much wiggle room. And you’re much more likely to fail to meet your deadline. On the other hand, if nothing has been agreed upon, then all urgency is gone and there’s little pushing you to get started. 
So for everything I work on, I make sure one of the two is firmly fixed, and I almost always choose time. A deadline. 
But how does that work? you may ask. Surely other people need to be able to count on what youre doing? 
Here are a couple of ways to resolve that:
1. The shadow deadline and milestones along the way
First of all: the official deadline is never my deadline. Whatever timeframe I agree to, I make sure my own personal deadline is earlier. You have to use a little discipline to make this work, but a buffer is a really, really nice thing to have (and has saved my skin more than once!)
Perhaps more important than buffers are milestones. I break all my work up into milestones. Instead of aiming for the final deadline for, say, a full review of my manuscript, I break the work into steps: go through the first six chapters of edits by Wednesday, finish the rest by Friday.
If I can tell by Tuesday that I’m going to fall short of my target, I can adjust. I can opt to move through the text faster and not as painstakingly to stay on schedule. And because of my shadow deadline, I’m still ahead of the game.
Working with milestones is also a great way to sustain motivation throughout your project. A deadline of a whole week means you still have room on Tuesday to think: I’ll do it tomorrow. But milestones within that week ensure you pace yourself, and pacing yourself can make your work better.
2. Underpromise, overdeliver
I think deadlines should be negotiable. But a client (or boss or colleague) is never going to accept an ultimatum like this: “Ok, you can choose. Either you decide when you’re going to hear back from me but you’ll have no idea what exactly I’m doing in the meantime and how far along I am. Or you decide precisely what you want me to do but you’ll have no indication of when I’ll be finished.”
Luckily, there’s a better way to get the best of both options:

  • Resist the urge to provide a time estimate on the spot. Ask for some thinking time to avoid committing to a deadline you’ll later regret. Planning isn’t easy and any deadline you name will greatly affect your work and how you feel about it. You’re certainly allowed to give it some thought first. 
  • If planning is a big part of your work, collect more data. Better estimates make your work easier. Start by keeping track of the work you do in a planner or spreadsheet. That helps you develop a clearer sense of how long things take. 
  • When possible, promise deadlines you can easily beat. Add an extra day to deadline estimates and deliver early. Or indicate that you’re not sure whether a certain part of the job is doable, and then make sure it’s done and done well (and on time). That’s the way to gain the trust of clients as a reliable partner. 
I’m convinced that deadlines – when used well and broken down into steps – make your work more enjoyable, not less. And you’ll get better results.
Have a great week!
Rick
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