"It ships on Monday!"
"We have a deadline to meet!"
"Why did you even set a deadline if you're going to change it?"
Deadlines. They matter until they don't. They are far away until suddenly they are right on top of us. Sometimes a deadline is sacrosanct, unchangeable no matter the situation or the quality of the product: one technology CEO I knew released his products on the day he promised them and nothing would change his mind. It was a point of pride for him to always release on schedule. His customers, however, were equally adamant that they wished it would be a point of pride for him to release products that worked. Yes, this particular CEO would release a non-functional product on the chosen date and then deal with fixing it in the field rather than slip the date and deal with the problems. Eventually, the customers won: they went to a competitor.
Other times, deadlines seem to be almost mystical talismans: setting a deadline will magically cause a product to be ready by that date. In one rather dramatic example from early in my career in high tech, the CEO turned to the head of engineering and asked him when the product would be ready.
"September 1st, best case scenario," was the curt reply.
The CEO nodded, picked up the phone, and said, "We'll have it ready by July 15th."
The head of engineering did a very credible job of not exploding.
When July 15th rolled around, the product was not ready. The CEO was shocked. His reaction was, "I set a deadline!"
Sometimes a deadline can spur people to dramatic action. Sometimes it can't. It's important to know which situation is which. When I was managing a team, I was once asked why I even bothered to set deadlines if I would then change them. The short answer was that it was because the only deadline that actually mattered was the one at the end, and that one we consistently managed to hit. How?
At the most basic level, deadlines are merely tools. They are powerful tools, but tools nonetheless. As will all power tools, it's important to know how to use them properly, lest your deadline prove fatal to your success.
At the beginning of any non-routine, non-trivial project, deadlines are basically little more than wishful thinking. Early deadlines exist to give you feedback: how well is your team working? How difficult is this project turning out to be? Will we be able to marshal the resources we need at the times we need them? Are we being aggressive enough? Are we being too aggressive? That feedback provides your roadmap moving forward. Therefore, start with small deadlines: don't rush forward in giant leaps which give you little information.
Whether you make those initial deadlines or miss them, the key is to be strategic: why did you make them? Why did you miss them? What are you learning about your team and your project? Early stage deadlines can be easily shifted and adjusted as needed, provided you don't lose sight of the feedback they are generating. Done right, the more flexible your early deadlines, the easier it is to hit your later ones. When you do miss a deadline, recalibrate! Don't just pile the extra work onto the next deadline; that only triggers a series of failed deadlines, which reduces productivity. Success is not how fast you can move, it's how smoothly you can accelerate.
As the project continues, you'll find that your ability to set useful, doable, aggressive deadlines will increase. You want your deadlines aggressive enough to excite and challenge your team, not so aggressive that people look and tell themselves that there's no point in trying. The secret to maintaining that excitement is simple: strive for deadlines that can be beaten with serious, but not unsustainable, effort. Beating deadlines increases excitement and builds a sense of success. Failing to meet deadlines has just the opposite effect. Quite simply, when people are ahead of schedule, they work harder, are more creative and innovative, and are better at problem solving.
Many a race ends with a final sprint across the finish line. How well you've managed the deadlines to that point will determine how hard the sprint is, and how much fuel your team has in its tank when you get there. If the team is exhausted and burned out, your deadline will likely prove fatal to your plans. On the other hand, if the team is excited and energized, they'll blast through that final deadline.
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