2 years ago I was asked the following question during an interview:

Your boss wants you to finish a task today, yet you do know you will need at least 1 more week till you're done with the task. What would you do? what will you tell your boss? How do you manage such a situation?

Back then I answered:

I would ask some of my close colleagues to help me, so I can finish the task on time.

But it looked as if they did not really like my answer that much, because they replied with:

what else would you do?

Now that I'm looking to switch jobs again, I would like to know how you would answer such a question.

P.S: I'm an engineer, so the question above relates to a position as an engineer.

  • hello, consider editing the question to make it better fit site topics laid out in help center. In particular, this guidance may help to learn what is expected of questions here. Good luck!
    – gnat
    Jan 30 '15 at 16:29
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  • @gnat well I don't see how this question does not fit the site topics. I don't rant or go on about how terrible a situation is. It is a simple interview question and there are thousands of these questions on this site. The way I see it, some people are very eager to downvote anything. I bet they are real fun at a party!
    – H_squared
    Jan 31 '15 at 8:01
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    @hhachem, it is a perfectly acceptable topic to ask about interview questions. Some folks just have very rigid ideas about exactly what questions are appropriate. The point of this question is to assess if you're willing to be realistic in the workplace even if it means having uncomfortable conversations. Sometimes the boss is simply wrong and needs to be told that. Many organizations go bad because people blindly try to please their management without regard to reality or good judgment; the question tries to suss out people that just say "yes" all the time.
    – teego1967
    Jan 31 '15 at 11:58
  • For an interview, you say what your accepted answer says. In reality, if this "same day deadline" happens often, start updating your resume as well. (This is what I did, and switched to another job, where my boss is not a clueless moron.)
    – Masked Man
    Feb 1 '15 at 15:47

What I do in real life not just an interview is to tell my boss the truth. These are the things that have to be done to accomplish that and this is how long they take and this is where I will have delays (if I need to get permissions changed for something for instance and that is out of my control - our IT group has 48 hours to get to a request like that.). Then I tell him what I can deliver in one day and perhaps we focus on the most critical piece of the task (Most critical to the users not to me) and/or I ask him to clear some roadblocks for me to meet the deadline or assign others to help. The worst possible thing to do is to try to meet the deadline and fail without having brought up why it will not be possible.

I do want it clear, that I am not suggesting you wait until you are one day out, but I assumed the question was about being given a task that day and expecting it to be done that day. Anytime, you feel the deadline is not going to be met, you need to sit down and make a plan with your boss to move things or mitgate the delay however you can based on the circumstances. Bad news shoudl never wait. Don't manage projects by wishful thinking. And no - work 24 hours with no sleep is not even close to an acceptable solution.

And, having been burned on this in the past, I would also make sure the manager told the client about the delay and the plan to mitigate. We lost a multimillion dollar client once becasue the devs (who were working nights and weekends already) told the manger the task couldn't be done a full month ahead of time and he chose to believe we would be able to do it and didn't tell the client who was very angry when the deadline came and then he asked for another month. Of course only a senior, well respected person can get away with pushing his or her boss that way.

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    Not only what you should do in real life, but also what you should answer in an interview. As an interviewer, that's the answer I would look for. Jan 30 '15 at 16:31
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    @DJClayworth, I tend to only answer interview questions with my real life answers. If they don't like my way of solving problems, I am unlikely to be happy there.
    – HLGEM
    Jan 30 '15 at 18:04
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    @JoeStrazzere, had this exact sitution come up just today and I did exactly this. I think this mindset comes from having done a lot of production support in addition to the dev work. The customer needed people to be able to login today, but the full fix to prevent a reoccurance won't happen until next week.
    – HLGEM
    Jan 30 '15 at 18:06
  • @HLGEM I didn't mean to imply anything different. In fact I just wanted to emphasize that for the questioner. Feb 1 '15 at 18:07

I would guess they "looked as if they did not really like my answer that much" and asked "what else would you do?" because you didn't answer the question:

I was asked

What would you do? what will you tell your boss? How do you manage such a situation?

You said

I answered:

I would ask some of my close colleagues to help me, so I can finish the task on time.

But that only addresses "What would you do?". It fails to address "what will you tell your boss?" or "How do you manage such a situation?". It is therefore unsurprising that they asked you for more.

Telling your boss that their deadline is not going to be hit would seem to be pretty key!


If I think the task will take me at least one more week, and my boss says it needs to be done today, then I can guarantee you one thing: It won't be done today. If I tried to do it today, the best possible outcome would be failure to finish it, the worst possible outcome is me producing something that my boss accepts as "finished", which then can be guaranteed to wreak havoc when anybody tries to actually use it. So I wouldn't even try it.

If the situation arises, then it is clear that some miscommunication happened. If there was a deadline for today that I was told about, and the task wasn't going to be finished today, then my boss should have been informed about it and it is my fault. (Not my fault that the task isn't finished; that depends on the task and the time that I had, but my fault if my boss didn't know about it). If that deadline was created just today, or I was only told about it today, then it is clearly my bosses fault.

Independent of whose fault it is, it's common sense that the task won't get done by someone demanding strongly that it gets done.


I would give frequent updates during a project. Not just at beginning and especially not at the end of a deadline.

This way, projects won't blow-up in his face and you will be able to make it visible through your updates that the remaining time given is insufficient vs remaining work. If he cannot read the signs, then always give a one line summary with each update. Say "All on track" or "Need to increase resources to meet deadline" or "Completion will fall short vs deadline due to reason1, reason2, etc if we cannot increase project resources or redefine deadline" or (gulp) "Failure imminent".

And you won't have to walk up to your boss to tell the truth A-Z story how you cannot meet deadline because your progress update prevents this kind of last-minute stuff from happening.

  • While I agree that on long-term tasks this is all true and I fully support the idea that you should talk to your boss as soon as you know there might be a problem, there are times when the task is a new one (or new to you having been taken from someone who failed at it or who left [we had someone quit with no notice leaving us 3 months of work and a 1 week deadline once] or who is out sick) with a ridiculously tight deadline. This is especially true if you do production support.
    – HLGEM
    Jan 30 '15 at 18:10

In the immediate case, you need to be completely honest with your manager. You need to give a brief rundown of why it can't be done until next week. You need to know what the factors are driving it to be done today. You need to prioritize the work at hand: maybe there's one feature that you could do today that will go a long way with the stakeholders.

But in the long term, this kind of "white flag" scenario isn't sustainable. You need communication with your manager and other stakeholders at every step of the process. You need at least weekly updates to ensure everyone knows where everyone is, what roadblocks there are, and what changes and/or new facts have come up that change scope and schedule.

Now, if this was something that you came in and your manager said "Hachem, we have an urgent fix needed for the Friday night batch job. If we don't, the Acme account won't get processed right and we'll lose their account to our competitor." You really need to find a way to fix that batch job. If you think it will take 40 hours to fix something that's going to run in 12 hours, there's going to be a problem. If it genuinely can't be done, you need to find an alternative plan. Halt this week's process. Remove Acme's accounts from the job. And no amount of pre-communication could have fixed this, at least on your part.

But more commonly, it's more like t Flux Capicator project was a 400-hour work effort. It started in June and finishes today. Your manager says "We've committed to delivering this product today." If you come back and say "It won't be done for another week." it's going to look really bad on your part. As soon as you thought you might not be delivering the product at the time you said you would, you needed to open a communication channel to all stakeholders. If everyone was receiving a weekly status update and a monthly catchup meeting, then you would have spent around an extra 20 hours in meetings and preparing updates, but that's nothing compared to the cost of delaying an application launch.


  • right now, find common ground, prioritize the work, make sure you can put other work on the back burner to finish the task as soon as reasonably possible.
  • in the future, communicate early and often about the current project status so people are aware of changes to scope and schedule as early as possible.

I would simply inform my boss in what state the task is on that day of the deadline, and what needs to be done to finish it completely. In this way, you're giving a clear view on the pending tasks, so that for example someone else can pick up where you left off. Also, if one of the tasks requires that someone else do something before you can work, be clear about it.

This is, of course, assuming that you've been keeping your boss up to date with the project news, and that you've warned him that the deadline would be missed.

Visibility is the key here. Don't keep the bad news to yourself, fail fast.


I update my resume.

The fact of the matter is that if I even have a chance of being a week over deadline, there's no way in hell that I'm waiting until the day before to raise it as an issue. Likely a week or two (or more!) beforehand, I said that I might not be able to get the work done in time. I will need help, or the deadline shifted, or scope decreased.

So my boss has known that the deadline was going to be missed (unless they helped me) for at least a week. If we've gotten to deadline day and I've got a week left, then they actively chose to let me fail. That is unacceptable.

  • "So my boss has known that the deadline was going to be missed for at least a week." No indication in the question that this is true. Jan 30 '15 at 16:35
  • @DJClayworth Telastyn has said that he's clearly communicated with the boss ahead of time, so there's no way the boss would be asking this question only 1 day before it is due. Jan 30 '15 at 16:41
  • @DJClayworth - Indeed as thursdaysgeek mentions, the entire point is that I would not let it get to this point. There is no success if we get there.
    – Telastyn
    Jan 30 '15 at 16:56
  • there have been... better answers to an interview question, which is what the OP is asking us to answer (real life mileage is different to the fantasy world that interview questions exist in).
    – bharal
    Jan 31 '15 at 2:32

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