Setting the Perfect Deadline


“I love deadlines. I like the whooshing sound they make as they fly by.”
Douglas Adams, English Humorist

During my first years as a web worker, whenever a client would ask me “When can I see the finished product?” I’d estimate the deadline in my head and give them an answer in 5 seconds.

Apparently, that was a colossal mistake which led me to miss more deadlines than I can count on both my fingers and toes.

After losing a few clients, I realized that I had to shape up and change the way I’ve been setting deadlines. Now, the process takes me much more than 5 seconds, and missing deadlines has been rare since.

So how can one set a better deadline?

Think of an initial deadline. This is the easiest part. When do you think you’ll finish that project? In a week? Two months? Just pick the most likely date.

Now, move your initial deadline earlier. Hofstadter’s law states that things take much longer than you expect them to. This is why some people adjust their watches 15 minutes earlier than the actual time.

Now, just because you should move your deadline earlier, it doesn’t mean you’re picking a random date either. Here are some things you should think about when setting an earlier deadline:

  • Make sure it’s humanly possible. If only a robot can finish your project at that time, then you’re setting it too early. Besides, most projects take longer than you think they take.
  • Look at your history. How often do you miss deadlines? Why do you miss them in the first place? Answering these two questions can help you evaluate your efficiency in the past, to see where your problems lie.

Add deadlines for milestones. Keeping your new, artificial headline in mind, set up deadlines for the smaller milestones or next actions for your project. Not only will it make your project more organized, but you can have a more realistic idea of when you can get things done.

Exert firmness. “So what if you moved the deadline to an earlier artificial deadline? You can always move it later!” This is the primary reason why I had a problem hearing deadlines whoosh by. The solution? Make those deadlines immovable – literally.

This is how I do it for Google Calendar: my virtual assistant shares a calendar with me, but she is the only one allowed to edit it. I let her know what my immovable deadlines are, and she sets them up in the calendar I can’t touch. I can’t ask her to move it, as when I was thinking clearly I’ve asked her to be firm with me. She’s like my sponsor for Procrastinators Anonymous. If you don’t have a VA, look for an equally firm equivalent in your life – such as your partner, a colleague, or a good friend.

However, your calendar might not have that feature I use for Google Calendar. If you use a different calendar tool, here are some alternatives to keeping your deadlines firm:

  • Sometimes, editing a calendar event may require a password. If this is possible, make this a password that’s made out of random characters you will never remember.
  • Move your calendar offline. If you write on an actual calendar with permanent ink, it’d be a hassle to remove and replace. (Of course, make a pencil draft first!)
  • Make it public. This is especially easy for bloggers to do – even if it’s only on your personal blog and only friends and family can read it. You can announce your deadlines before the project starts and make daily updates on your progress. Doing this via Twitter is also an option. The theory is that if everything is out in the open, you’ll be more ashamed to miss that deadline.
  • Understand that it’s a domino effect. To miss the first milestone deadline will mean you’re likely to miss the next, which may have messy consequences for all parties involved in your project.
  • Know the cost. Sometimes, attaching monetary value to something can make its cost seem more realistic. If you miss your deadline, you might get paid at a later date, and what effect will that have? Will you be able to pay your bills on time? Does it mean you’ll buy that new gadget a week later than you planned?

What date do you tell your clients? I usually give them the date 2 to 3 days after the initial deadline I’ve set, but the allowance you give yourself will depend on the extent of the project.

Once you tell your clients the later deadline, forget about it. Don’t mark it in your calendar. The only time you should recall it is when you’re contacting them that the project is finished, and you’re looking at your email archives to find the date you promised. Of course, your email should be along these lines: “Good news! We’ve finished the project ahead of schedule!”

After all, you should be the one whooshing past your deadlines, not the other way around.

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