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  • New Boss:"Is the deadline realistic? Answer yes or no. No maybes."
  • Me:"Well, no..."
  • New Boss:"That's an unacceptable answer. We must meet that deadline."

That's just one of many examples of a typical conversation with my boss about managing expectation. He initiates as if he is interested in hearing my information, but lambasts me if they do not correspond with his expectations.

He does this almost on a regular basis and the consequence is that I and the team reporting to me have to work very abnormal hours in order to always give a positive ("acceptable") answer.

How do you approach this kind of "managing upwards" problem?

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  • If this one is not terribly helpful a quick search of the site for deadlines turns up many other results as well. – IDrinkandIKnowThings Aug 25 '14 at 2:05
  • Did you tell your boss you have the team has to work overtime to meet the deadlines and is your boss/team ok with the consequences of doing that – Brandin Aug 25 '14 at 7:21
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"I love deadlines. I like the whooshing sound they make as they fly by." - Douglas Adams

New Boss:"Is the deadline realistic? Answer yes or no. No maybes."

Do you work in a law firm - this is a classic barrister's question? That is, the boss is not seeking information, he is seeking confirmation. The solution is to defuse the question by making his assumptions explicit, like:

Me: With our current resources, no. However, if we got x more y's then it would be achievable.

This way you have given him the facts and offered a solution to his dilemma.

A point to remember that a mentor of mind told me: "The client will forgive you for being late; they won't forgive you for being wrong". This gives you the alternative formulation of:

Me: Yes, but we wouldn't have time to test/debug/verify (whatever is appropriate for your industry) thoroughly. I wouldn't be happy delivering in that state but its up to you.

It sounds like your boss (and you too) have trouble saying no. There are only 24 hours in a day, summer and winter alike, therefore there are only a limited number of things that one person can do within one. It seems that you have already decided that by saying yes to your boss you are saying no to your social life (or sleep).

In addition, 2 people cannot do twice as much because they must spend part of that time coordinating their activities - as outlined in The Mythical Man Month.

You need to bear in mind, and draw your bosses attention to, the fact that a person who says "yes" to everything will achieve no more (and probably less) than a person who chooses what to say "no" to. The "no" person is consciously deciding what to do and what not to do; the "yes" person is not deciding what doesn't happen - it just doesn't.

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  • Great answer. Bosses also have to answer to a board or their bosses. Provide a solution to for them to handle their superior and you will get what you want. – zhengtonic Aug 26 '14 at 9:54
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It doesn't sound like you have any idea what expectations are being placed on your boss. Have some discussions about the "big picture" kind of stuff to know what is important to him. Maybe he has the ultimate decision, but usually there are at least client expectations that are involved as well.

Usually, the people doing the actual work, have the best idea about how long it will take. Try getting your team involved in the requirements and expectations of the projects and then setting solid due dates based on working normal hours. Don't try to appease clients by giving them due dates that will make them seem happy only to fail to meet the deadlines.

As far as I can tell, your boss either isn't aware of the time commitment your team is making to meet these deadlines or he doesn't care. It is up to you to try and get more involved in these decisions and stand up for your team. Let it be known they can't keep this pace up forever and there is a risk of losing good people. This is going to cause more missed deadlines in the future. Your job is to help your team to be successful.

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The way that you describe it, there seems to be no chance for you of "managing upwards". Working what you call "abnormal" hours is known to destroy productivity within a short time, that is in a matter of weeks. It's also known to destroy you and the people reporting to you.

This is usually frowned upon here as advice, but in your case it looks like a good idea to search for a new job, and at the same time making sure that your bosses demand don't damage your health and wellbeing. As a manager of a team, it is up to you to decide whether it is more ethical to give them honest career advice, or to support the interests of your boss who is damaging them.

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    I feel like the main thing we're looking to avoid is a bunch of "dude, that sux, just quit bro" style answers. With that said, if you do think of more information to support the idea of moving on, or if maybe you can include some things to try before making the call to move on, I think that would definitely add more value. Hope this helps! :) – jmort253 Aug 25 '14 at 0:58
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New Boss:"Is the deadline realistic? Answer yes or no. No maybes."

Me:"Well, no..."

New Boss:"That's an unacceptable answer. We must meet that deadline."

Me:"OK, what is it you want me to drop, or to put on the back burner?"

New Boss:"Nothing"

Me:"I heard you"

(My team and I will make no special effort - Resumes are being updated and recruiters are being contacted. Complaints that the new boss won't do his job of working with the team on setting priorities and milestones flow upward to the boss's managers)

Me: "We won't make the milestone for that project"

New Boss: "I had told you that's unacceptable!"

Me:"And I had told you that I heard you"

New Boss: "So what did you do?"

Me:"All we could"

New Boss: "That's unacceptable"

Me:"We did all we could. We can't do more than that"

New Boss: "That's unacceptable"

Me: (saying nothing - I am putting him on "ignore", that includes any threat of firing)

(Memos are being sent out to the boss's managers, blaming him for the failure to meet the milestones and stating that he owns that failure)

My style is pretty confrontational, eyeball to eyeball - just about the only time I'll look at someone in the eye - and I am not afraid of being fired.

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    This is called 'setting someone up for failure'. It usually does not work because the other partly feels confronted/boxed in etc., with a big chance that he retaliates. So your answer might as well be 'find another job'. – user8036 Aug 25 '14 at 13:06
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    @JanDoggen The other party is sure to try to find a way to retaliate. However, cutting back on the overworked staff is not going to speed things up. In fact, it's the equivalent of cutting one's nose to spite one's face. I acknowledge that there are people, bosses included, who are quite willing to cut their noses to spite their faces. I have been fired a couple of times by such bosses, with the firm going out of business 12 to 18 months later. In these two cases, the CEO was my boss and I had no one to appeal to. I dispute that I set them up for failure - THEY set themselves up for failure. – Vietnhi Phuvan Aug 25 '14 at 13:20

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