If your company is like the typical digital agency or software shop, you've got deadlines slapped on every bit of work in the entire organization as a way to get your people to deliver work quickly.
If you're honest with yourself, you know that your people will miss their deadlines on plenty—if not most—of the work they do. And while you might crack the whip and fuss about it, you know deep down that it's expected. You're upset about it, but that's just how things are. How else could they be?
The trouble is this: your people know it's expected too. The deadlines don't really work as an incentive, and the side-effect is constant, corrosive stress. You never intended to run a burn-out shop, but here we are.
But hey, that's all just part of doing creative work. How else could it be?
So when something really does have a deadline, like a t-shirt design for a trade show giveaway, don't be shocked when your people don't take those deadlines very seriously. You've been training your people not to take them seriously all along.
How do you make deadlines meaningful again? Use them sparingly. When the outcome of your work has zero value if it's delivered after a given date, that's work that needs a deadline.
For everything else, there is no deadline. There never was.