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I work beyond normal hours quite regularly (often continue at home after dinner) and occasionally I finish working on something but don't "Send" or finish the very final part just because I get too tired or fall asleep.

Then I realize I didn't do it only after I wake up in the morning.

What's the best way to communicate something like this happened without appearing in a bad light?

Especially if the deadline was due to another timezone of the company requiring that work? e.g. I finish the work by end of my day so that another team on the other side of the planet can take over from there.

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    Let's say if I was the one in another country waiting for your work to arrive, and you told me what happened, that you worked on it after going home until you were so tired that you fell asleep and that's why you didn't send it, I would go straight to my manager to talk to your manager to stop you from working overtime. I wouldn't blame you one bit, but I would really blame your manager. Assuming it's the same company, my manager might ask his manager to talk to your manager's manager as well about your work practices. – gnasher729 Sep 24 '14 at 9:23
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Firstly, there is no way that you will not appear in a bad light here. You promised to do something, you were unable to do it - people will be somewhere on the scale of disappointed to angry.

There are two things that you need to do in a situation like this:

  1. You need to acknowledge and report the fact that you did not meet the deadline
  2. You need to change the way you work so that this does not become a regular occurrence.

Acknowledge and report

You need to do this as soon as possible. If you're close to finishing, but have the very final part left, and you're realizing that you won't be able to manage the rest - send what you have and explain why a part is missing. If I were the recipient, I'd rather have 95 % of a report than 0 %. If you literally fall asleep at your desk before hitting "send", you should send it with an apology as soon as you wake up.

Change the way you work

This is the most important part. If missing a deadline was a one-off occurrence, an apology and an assurance that "it won't happen again" would be sufficient. But it's not - you repeatedly find yourself in a situation where it's not possible for you to meet a deadline. This means that you need to change your work patterns. I can't tell you exactly how to do this, but here are some suggestions to consider. But first, talk to your manager. Explain that you are having problems with tasks requiring you to put in very long days to the point that you literally are unable to finish due to lack of sleep. Ask them to help you change the way you work so that you can deliver your product on time. You will need their support to fix this, and your fixing it will reflect well on your manager.

  • When you get a request with a deadline which will require you to work late, say no. Explain that it is not possible to meet this deadline, suggest that you can do X percent of the work within that deadline and you'll turn the rest in within Y days. This is something you really need your manager's support with; if they don't back you up, you're sunk.
  • If you often have the kind of jobs that are given to you late in the day and will require you to work after hours due to timezone issues with other departments, talk to your manager about adjusting your hours so that you can start later. That way, if you need to work until 10 pm, at least you will have been able to sleep in a bit first.
  • When you do need to work late and are tired, set up a reminder to yourself to send the work in at a given time, whether finished or not.
  • Send the work in in increments. It's better for the recipient to have part of the work than none of it.
  • EDIT If you need to deliver something at, say, 2 am, then don't start working on it immediately when you get home from work. Instead, have your dinner and get an hour or two of sleep. You will be a little more rested and you will be more efficient and effective at your work.

As a sysadmin, I've occasionally had work to do that could only be begun after business hours and that needed to be finished before a set time. On those occasions, I would get to start late in the day so I would be well rested when work started, and I would not be expected to be in until the following afternoon. I would also know that restoring the service would take e.g. 30 minutes, so I would not continue working with the job too long - I would always make sure that I wrapped up the job (even if unfinished) in sufficient time that I would be able to spend those 30 minutes to get the service back online. I would also plan for the time to send my report to my manager and anyone else concerned, and I'd take the time to jot down notes during the work so that I didn't have to formulate the entire report after the work was done.

Oh, and also remember to eat properly - coffee and sugar isn't sufficient, you need actual food to keep going. Eating something with actual protein and fat will keep you focused a lot better than three cups of coffee.

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    There are times to accept a task that will require that you work late, when it's really critical to the company. (I've done so on support for major customers or major projects.) But even if you do so, you need to be realistic about when you can complete the work. If you're down to the difference between pushing send in the evening vs. the next morning, you've already gotten your estimate wrong; admit it and refine your estimating skills for next time. I find that on larger projects I need to at least double my instinctive man-hours estimate to get an approximation for actual work-hours needed. – keshlam Sep 24 '14 at 13:14
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What's the best way to communicate something like this happened without appearing in a bad light?

If the deadline was something you committed to without external pressure, the best way is probably to state you overcommitted, learned from it and will commit to less on your next deadline.

If the deadline was established by your manager/boss (without taking your input into account) then you should raise a couple of alarms and point out most of the problem appears from overtime itself:

"I work beyond normal hours quite regularly (often continue at home after dinner) " - as a client I wouldn't want a product/service that is done on "after-hours work quality". The fact you have to do overtime on your project is a sign of poor management/planning.

"occasionally I finish working on something but don't "Send" or finish [...] because I get too tired" - typically, work when you are exhausted is exceptionally lacking in quality. When I did overtime (I am a consultant now, so it doesn't happen anymore), I used to have situations when I would work on a problem for an entire evening (4hrs+ after work), then give up, come back the next morning and solve the same problem in 10 minutes.

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    I've found that when I've worked too many extra hours in an evening that the next morning I have to spend an hour or two fixing what I messed up, before I can make progress again. – thursdaysgeek Sep 24 '14 at 15:35
  • This does not really answer the question of how to explain the problem rather you seem to be berating the OP for working in a manner you disagree with. – IDrinkandIKnowThings Sep 24 '14 at 19:09
  • @IDrinkandIKnowThings This might not directly answer the question but it does address the root cause of the problem. – Jørgen Fogh Oct 22 '16 at 22:10
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What's the best way to communicate something like this happened without appearing in a bad light?

You can't, as you say you've missed a deadline, no matter what the reason, that's bad.

You need to set expectations accordingly before, either commit to less, or drink coffee/keep the AC low/have a cold shower to keep you going, but missing a deadline is missing a deadline.

I'm assuming this is working at home, and you aren't falling asleep in the office, looks like you/your team are over commiting if this is a regular occurrence, and addressing this is the primary solution.

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