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Scenario/Background: I have two bosses, with one of whom I manage variable daily processes (priority 1), while the other one gives me longer term projects (priority 2). Due to the extreme variability of the daily processes workload, I am normally free to work on the projects whenever I am not busy with the daily processes - in fact, I have no deadlines on the longer term projects as long as I complete them within reasonable time.

If at any time the project boss asks me by when I can finish something, I normally state an estimated time with an ample buffer and often finish before that.

Recently, however, there have been entire weeks during which I was nearly 100% busy with the daily processes and thus had no time for the projects. My project boss noticed this and started setting deadlines - however, this meant that I often need to work after normal hours.

The problems started when the project boss started becoming impatient due to his own superiors' deadlines. On one day he came and asked me to finish something on the very same day, because the CEO needed it ASAP.

I had other personal appointments scheduled on that day (it doesn't really matter what type of appointments, or does it? It could be anything, doctor, kids, an old friend, a trip!) but canceled them out of fear of being fired if I didn't finish by the new deadline.

However, I now think that it's time to stand up for my... time, and thus I would like to ask what is the best, most diplomatic course of action to refuse sudden, last-minute deadlines - especially if they are in conflict with other commitments I have already made!

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Does your project boss know how many hours you spend on his tasks every week? If he sees that it's close to zero is ought to be apparent for him that the root problem is that workload from prio 1 tasks have increased, and that is not something he can solve by managing you differently (setting harder deadlines or whatever). –  Buhb Aug 8 at 6:14

3 Answers 3

One of the only ways I've found to deal with having two masters is to make them sort out the issues between themselves. I might be tempted, in your situation, to start with an email status update to BOTH bosses giving your status tasks, your ETA on tasks due and reminders of any time away. Then they are informed and if they don't like the status, you can tell projects boss that he/she needs to talk to daily tasks boss about freeing up time for x project.

That said, there ARE occasionally things that must get done asap and I do allow for occasional crises but again try to get the two bosses to sort out amongst themselves what time is spent where.

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+1 - Excellent approach! I'd add that you'd like them to tell you which one of them is the "final" authority you must answer to. –  Wesley Long Aug 8 at 4:11

If you have a previously scheduled personal commitment, then you say that you have a previously scheduled commitment - That's the price they have to pay for telling you at the last minute.

If they want something from you, they don't wait until the last five minutes before they tell you. I hate it when I have to bail out someone for their inefficiency. Don't jerk me around and don't yank on my chain.

Having said that, I usually do whatever it takes to get the job done and beat the deadline. After I take care of my personal appointments.

If you let your boss make extraordinary demands and you are complying without a murmur, you are not negotiating. You are bending over. You need to push back as you have only so much time available during the week to take care of personal business.

Your bosses have options available to them at their level such as assigning someone else, getting more people assigned to projects, de-escalating less urgent priorities. Make them use these options. The process of assigning work above and beyond should be a process of constructive negotiation, accommodation and mutual adjustment.

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"If you let your boss make extraordinary demands and you are complying without a murmur, you are not negotiating." Not only are you not negotiating, you're establishing a precedent that says "handing me tasks at the last minute and expecting them to be done the same day is completely acceptable". It's best to avoid setting precedents like that. –  aroth Aug 8 at 1:21

My project boss noticed this and started setting deadlines - however, this meant that I often need to work after normal hours.

When you have work-related tasks that you cannot do because of other work-related tasks, notify your manager. It is his job to ensure your tasks do not conflict with each other (i.e. "manage" your tasks).

This means, if you have two (or more) managers asking for your time, have them fight it out between themselves. When the second request comes in, tell the manager you will be able to get to it only after he confirms with your first manager (and lets you know), or after he tells you the responsibility for the first task not getting done, will be his.

I had other personal appointments scheduled on that day (it doesn't really matter what type of appointments, or does it? It could be anything, doctor, kids, an old friend, a trip!) but canceled them out of fear of being fired if I didn't finish by the new deadline.

It kind-of does matter (not because anyone else gets to decide what you should do, but because you may decide to reschedule); if you can afford to cancel your personal appointment, offer to do so (preferably notifying your manager that you will take your time off, later). If you cannot reschedule/cancel your time (or simply do not want to), point it out ("I'm sorry but I cannot be in office this afternoon - I had notified X of this yesterday through email and he said it was OK").

what is the best, most diplomatic course of action to refuse sudden, last-minute deadlines - especially if they are in conflict with other commitments I have already made!

If the other commitments are for company interests, have your managers decide your schedule. If they are for your own interests, decide for yourself (and once you get a confirmation that it is OK to get time off, that means it is OK to get time off - no matter what happens in the company).

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