There are some bosses who give you the task with a fair deadline and trust you to deliver it and then let you on your own. There are also people who give you unfair deadlines and expect you to stay later and get the job done while the actual deadline for that task is not what they tell you.
They usually do this to keep you productive and prevent you from wasting time. This may not work for everyone specially for people who are productive on their own and care about the job.

In the first case you have several tasks at hand and can freely coordinate them and do them accordingly. But in the second case you have to stop what you're working on and keep switching the context to the new task that you're given.

Are there ways to change this behavior? How should one handle such situations?

  • Final close vote cast: this question is too hypothetical to be answered constructively. For advice on handling a situation we'd need details of that situation as they're important. As for ways to make bad managers stop being bad at managing people: I doubt there are any. – Lilienthal Feb 29 '16 at 18:34

Short answer: Approach your boss with your own quantifiable estimates as to how long you need to do the job. Make sure these are achievable and detailed enough to be credible. Unless you can show that the deadlines are unreasonable, then you have no chance of arguing the point.

There are some serious issues in the project management process here that you need to talk to your boss about here:

  • Who did the estimates for the project?
  • On what metrics/baseline were the estimates based?
  • Where is the scope defined?
  • What "fudge factor" was built in? Who built it in? Based on what?
  • What are the priorities?

If your boss is basing their estimates on their own time for doing the job, that's an issue. If they're arbitrarily choosing a date, that's an even bigger issue. You need to ask how the estimates were calculated. Then you need to be able to give your own estimates to your boss. Be detailed and specific. The more granular you can be, the more accurate it will be and defensible. You can't just say "I can't make this time frame" without giving evidence as to why the deadline is unrealistic. Otherwise, it's no better than what your boss is doing to you. So where you need to focus is on have quantifiable estimates.

Now, when you are working on a task, you need to:

  • Raise immediately when you realise that can't make a deadline. The earlier the better. You are trying to mitigate risk, and that can only be done if there is sufficient warning to change time frames, scope or resources.
  • Ensure that your own estimates are realistic. If you argue about giving your own estimates and you're always late, then it's not going to go over well. Factor in enough time for the unexpected.
  • Understand where you fit into the big picture. If you have five tasks and three of those are dependent on an external resource, start on the other two and raise immediately if you are held up on the dependent tasks.

In a nutshell, unless you can counter that your boss's estimates aren't accurate with estimates of your own, then you have no way of arguing the point.

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Firstly, itemise the work and projected timeframes for the various sections, also list your existing duties and time needed for them (if any), and then discuss with the boss if it's unrealistic to accomplish in working hours. Do that with a written list, reiterate by email after the meeting as if you're clarifying.

You now have a paper trail if deadlines are missed, your back is covered, so get on with the job.

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Very few of us are so gifted that our benefactors are willing to wait for our next masterpiece. Later in Dr. Seuss's career, he never had a deadline. His publisher just waited for the next book.

Developing a level of trust, can take time and a lot of effort. As a manager, if I knew I could count on someone to work late and get a project done, even though she felt this request was arbitrary, I would like to think I would let her manage her workload a lot more and I wouldn't abuse the situation. That's just me.

While you're job searching, develop strategies to determine the manager's style. This is difficult. Few people in the modern workforce, will tell you, "What I say goes. My way or the highway. When I say jump, you say how high." They may hesitate to respond. Or worse is the person who jumps up and down and screams about how hands-off they are. Try to ask others in a similar position how they manage their day and how are emergencies handled.

Say NoYou can always say no. If you feel you have plans for that evening, you can see if there is any way to do it in the morning.

Flex Time If you're occasionally asked to work late, see if you can off-set it by coming in later the next morning.

Everyone is different in how they interpret fairness and what works for you. If a company gives you stock options that could make you a millionaire, you'll probably be asked to do what you may think is impossible only to find out it is.

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