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Esquire Guy

The Esquire Guy on the Right Way to Miss a Deadline

Magazine Contributor
Articles Editor, GQ magazine
6 min read

This story appears in the September 2014 issue of . Subscribe »

The key to missing deadlines is, first, to miss them morally: fully aware of the problems you're causing other people and generally aware of the reason you're missing the deadline. (Note the active voice there. You--or your company--are missing the deadline. The deadline isn't being missed. For example: I am turning this column in late. The column isn't being turned in late. Responsibility must be assumed. And you are the one to assume it. Me, too.)

The first part is easy: However much you think you're negatively affecting the party to whom you are not delivering the work, multiply that by three. Hold yourself accountable by recognizing your role in a larger system of deadlines.

And you must recognize the deep psychological underpinnings of your lateness. There are lots of reasons we procrastinate. It might be because we're incapable of doing the work (unlikely). Or it might be because we think we're incapable of doing the work. Or it might be because we'd rather be thought incapable than inferior, which is a common phenomenon among creative workers. (Megan McCardle's book on "failing well," The Up Side of Down, devotes a fascinating chapter to this concept.)

The common thread here is image, says Joseph R. Ferrari, a professor of psychology at DePaul University in Chicago and author of Still Procrastinating? The No-Regrets Guide to Getting it Done. "We call it social esteem in psychology," he says. "Self-esteem is how I feel about myself; social esteem is how I feel about how others view or judge me. Procrastinators would rather give a projection of a lack of effort than lack of ability. A lack of ability is stable; it means no matter how much I try, I can't cut it. A lack of effort is not stable; it means I might be able to really do this."

Procrastinators hold on to the maybe, the possibility of success--no matter how slim.

But our concern here today is not with why you're missing a deadline--that's your problem--but how to miss it. Which is both your problem and the problem of the other party. How can you recover, apologize, use your failure--and it is failure--to strengthen the relationship you've injured? How can you foster trust in a situation where your trustworthiness is being called into question? The rules of how:

1. Do not say why you are missing your deadline

Because no one cares.

No one.

Not even the person who is waiting for your work.

You don't even care.

I certainly don't care.

Don't look at that guy. He doesn't care either.

No one cares.

So don't mention (by phone or text or carrier pigeon) why you're missing your deadline. Just acknowledge that you missed it--or you're about to miss it--and when you will turn in your work. The most useful thing for the other party: having your work in their hands. The second most useful thing: knowing when that work will come in. The fact that you're "swamped" is the 1,432nd most useful thing, right behind how much you think chickpeas are underrated and the dream you had last night about boxing with your grandmother. (Weird, right?)

Dr. Ferrari is pretty much fed up with all of our excuses, too. "I think people who miss deadlines have life focused all about themselves. Life is not about me, life is about we, and if I delay, someone else has to delay."

I was saying the same thing, doc--

"It's a snowball effect. People don't get that. I don't like that, I don't have the time. Suck it up, we're all busy."

Right, but we're so much busier than--

"Our lives aren't busier today. What an insult to our ancestors to say we're busier today. They had to get up and plow the field, make sure the buggy was working, fix the roof, get the pump working …"

What about feeding the--

"… feed the animals. You can't manage time; you manage yourself. Time-management is a misnomer. We can't fix the wind; but you can adjust your sails. This notion of missing deadlines because we're busy: no. Because we're creative: no. It's not about you, it's about us. When you delay, you're impacting other people. We are great excuse-makers."

Thank you, doctor. We all needed--

"Reframe it, rethink it, stop the excuse-making."

Got it.

2. Disclose your failure as soon as you know you've failed.

Advice from Jeremy Conrad, co-founder of San Francisco-based investment group Lemnos Labs, which works with a dozen hardware startups at any given time. With all that time spent working with early-stage companies, Conrad has a good understanding of the challenges entrepreneurs face and the best approach for addressing delays.

"The worst thing you can ever do is tell them at the very minute it was due," he says. "A single component delivering late can cause everything to stop. Vendors don't want to admit they're going to be late, so it's important that we say, 'It's OK if it's late--it's not great--but I'd much rather have you give us notice that it's late than just get no product delivered at all.'" If people can't have the product on time, they need information.

3. State a new deadline.


4. Stay off social media unless your social media musings relate to how much you're working on the project you're turning in late. And even then, I mean, come on.


5. Meet the new deadline.


6. Finally, reiterate your regret.

For example: "Here's the column. I want to apologize to you and anyone else who was inconvenienced by my lateness, which belies the respect I have for you, the magazine and its readers. And sorry for the tweeting."

Key Technical Matters

  • As soon as you know you're going to miss your deadline, apologize emphatically.
  • But don't make excuses.
  • Don't say you're swamped.
  • Or slammed.
  • Or overloaded.
  • Or being pulled in all directions.
  • Unless of course you are literally in a swamp or being slammed or overloaded or pulled in all directions.
  • After apologizing and not making excuses, establish a realistic and firm new deadline.
  • Meet it.
  • After you have turned in your work, ask yourself why you were late.
  • Is it because you took on too much work?
  • Is it because you didn't know how to do the work?
  • Is it because you were afraid your work would not be good enough?
  • Is it because you would rather be deemed irresponsible than incompetent?
  • Is it because you are on island time?
  • In any case, the key to meeting deadlines is to understand the reason why you're missing them.
  • The key to regaining trust is to make sure the other party knows how regretful you feel.
  • Note: Island time is not a thing.

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