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Advice / Succeeding at Work / Productivity

How to Ask for a Deadline Extension Without Losing Your Street Cred

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So, you kinda underestimated how long that new project would actually take. Or, you felt pressured to overcommit and now have way too much to do before Friday. Regardless of the situation, you’ve done the math—and there simply aren’t enough hours in the day to get everything done on time.

Fortunately, we’ve all been there. So, in many situations people will be willing to be grant you some extra time. Of course, you want to be sure to ask the right way. What you say can make all the difference in how the person responds as well as how it will affect your future responsibilities and assignments.

Keep these dos and don’ts in mind as you attempt to score yourself some breathing room while keeping your reputation intact.

Don’t Take it as a Given

Yes, there are situations in which a few days here or there really won’t matter. But there are also times when being late could be disastrous. Like if you miss a deadline required for funding. Or submit a late job application to a company that refuses to review tardy submissions. Or if you’re behind with stage one of a project and the people charged with stage two can’t do their work in the meantime. In these instances, reaching out with a simple, “I’m running behind and could really use an extra few days,” will rile up the person you’re working with.

So, how can you tell when an extension wouldn’t make a difference from when you’re better off not asking at all? Send a test balloon. Before you see if you can have extra time, ask: “Is there any flexibility with deadlines for this project?” Or you could try something like: “I wrote August 15 on my calendar, could you remind me if that’s a hard deadline or if we’re generally targeting the middle of the month?”

These sorts of statements give everyone an out. If the exact dates don’t matter, you’ll know and feel more comfortable following up and asking for more time. If there is no flexibility on the other end, your client—or boss, or hiring manager—will tell you. In that instance, your next step if to revisit your to-do list and see if you can push something else.

Do Set a Reasonable (New) Deadline

You just need an extra day, so you email and ask for 24 hours. Those 24 hours pass and you realize that if you had another additional day you could make it that much better, so you ask for another 24. And then you do that one more time—but all told your work is only three days late and now it’s exceptional, so it’s all good.

Except, for one thing, this approach does not make a great impression. First, instead of asking for a break once, you’re literally providing the other person with a daily reminder that you didn’t complete your work on time. Second, each time you send that request, you’re also asking someone to receive and send an extra email—and you know how people love that! Third, and most importantly, there’s a good chance your work had that deadline for a reason. They’re rarely completely arbitrary.

So, when you initially inquire about more time, suggest an attainable new date. If you have a crazy week, don’t ask to push your deadline one day; ask if it would be possible to push it to the following week. If, per above, the new date won’t work for someone, she’ll tell you. But like negotiating anything else, if you end up meeting in the middle (say she says you have until Friday—latest), you still have more breathing room than if you gave yourself one day.

Oh, and that revised deadline? Do everything in your power to meet it.

Don’t Wait Until the Last Minute

You decide to save yourself the uncomfortable conversation and not ask at all. After all, if your first meeting finishes early and your second meeting is randomly cancelled, and you pull an all-nighter, voilà! The project will be done on time.

But, if you don’t find those extra hours—or if you fall asleep at your desk—you’re in trouble. Because even if your work isn’t time sensitive, it looks seriously unprofessional to ask for more time right before something is due. Then you’re left contemplating drastic measures from winging an entire presentation to calling out sick.

At this point, you need to gauge the relationship. If it’s your boss or someone you have a positive track record with, you could admit that you took on too much and say, “Unfortunately, I’m still in the early stages of drafting the document. Would you like to see what I have or would you prefer for me to reach back with a polished version at a later time?” (Also, don’t be surprised if there’s a follow-up discussion at some point about how you’re managing your workload.)

If it’s your first time working with someone, asking for an extension the morning of can set a very negative precedent. In this case, your best bet is to send an early version and say you’re prototyping and hoping for feedback, or triage and pull together the best effort you can in the time remaining.

Do Take Steps to Prevent it From Happening Again

So, you asked for an extension and were granted one. All in all, it wasn’t that hard. But unlike so many tough conversations in your career that get easier every time you have them—this is not something you want to repeat.

So, if you keep feeling like you’re faced with an insurmountable of work, try to go back to the source. If it’s a boss, client, or colleague use one of these scripts from Muse columnist Alexandra Franzen to say, “Help! I’m Drowning in Work.” If you’re self-employed, consider scaling back for a bit and then adding more work once you have a better handle on your schedule.

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