How to Annoy Your Boss (14 Real-Life Tips)

I guess all of us read Dilbert, right?

That’s because everything in Dilbert is true! Scott Adams is holding a mirror to every organization, and all employees suffering from bad managers. But I believe I can offer a little help to all readers who need to work with pointy-haired bosses.

When your boss makes your life at work miserable, why don’t you retaliate by using some of these tactics? Your boss will notice that you are a smart person, and will start to recognize you as an equal. These tactics are all inspired by my personal experience as a manager, so I know they really work!


  1. When asking for some days off, wait as long as possible, and try to arrange for other team members to ask for the same free days. Make sure to buy flight tickets before requesting days off.
  2. When you send an email message to your manager, make the number of people in the Cc proportional to the number of complaints in that message. If it’s really serious, send the Cc to the whole organization.
  3. Your standard reply for any team problem should be that communication by management is abysmal. If your manager doesn’t agree, ignore him.
  4. Tell your manager you cannot find a document if it doesn’t have a direct hyperlink on the homepage of the organization’s intranet. Use this same argument for any of the 100,000 documents in the organization.
  5. Dig up an old e-mail message that you ignored 3 months earlier, and reply to it as if you only received it an hour ago. But first verify that any need for an answer has long faded away.
  6. To any urgent verbal request from your manager, reply that you will be working on it straight away. Then ignore it. Repeat this procedure until your manager starts turning blue, then send your manager a hyperlink to some web page about “servant leadership”.
  7. Tell your manager that you can never find the time to work on self-development, because of the sheer size of your workload. Then one hour later, book a lengthy vacation.
  8. Set your internal spam filter to the highest security level, and use the standard reply “nobody told me” for any company rule violation that you are being accused of.
  9. Don’t fix problems, only create workarounds. If the workarounds don’t work, then repeat the procedure: don’t fix the problems, create workarounds.
  10. When asked for input about improvements, try to come up with the silliest, most unworkable and most expensive ideas imaginable. Then complain that management never does anything with the input they gather from employees.
  11. Be late at every meeting, except the ones that don’t seem to be very important.
  12. Select any two arbitrary departments and complain that there’s too little communication between them. One hour later, complain about time wasted in too many meetings.
  13. Order twenty books (or even better: borrow personal copies from your manager), but don’t read them. Use them as a monitor stand, as a paper weight, as an extra chair, or as a door stopper.
  14. When you have a question for your manager don’t ask it directly. Start explaining your situation with as many details as possible. Repeat this procedure, while looking hurt and misunderstood, until your manager is able to formulate your exact question.

(Thanks to Perry, Edwin, and Cornoud for some suggestions.)

Disclaimer: This is a work of fiction. Any resemblance to real situations and real people in my organization is pure coincidence. I know they are reading this. And I love them dearly. 🙂

(picture by Jan Tik)

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  • Angelo

    Quite an interesting post. Though I am curious. You mentioned in the title “14 Real Life Tips” and in the bottom of the post, you placed a disclaimer. So which is which?
    How about, posting something that would Impress Your Boss? Probably a listing of 30 or less of those things that would calm down your boss and make him/her impressed.

  • Srikanth

    Jurgen, you’re the man!
    You know, my friend really needs this and you couldn’t have written at a better time than now. I’ve sent him the link. Let’s see if he’s gonna get fired 🙂
    No, the friend is not me.

  • Jurgen Appelo

    @Angelo: Yes, these tactics are *inspired* by real life, but I don’t want to implicate any specific people and situations. I agree this might be a paradox. 😉
    Thanks for the idea on How to Impress Your Boss. I might use that some day!

  • Jurgen Appelo

    @Skrikanth: is your friend a manager or a subordinate? 😉

  • Heather

    If I didn’t know better, I’d think you were a little bitter. 😉
    But I do agree it’s a good set of tips… sometimes we don’t realize exactly the headaches we’re causing for our managers.

  • Omer van Kloeten

    Funny article. You could also go over his head and keep him out of the loop, cc-ing him to the concluding emails. 🙂
    On a more serious note – I would just have a conversation with my boss, telling him what’s wrong. If that didn’t work, I’d go above his head and if that didn’t work, I’d use the thread of quitting and eventually simply quit.
    You don’t have to suffer. There are enough jobs in the world, you know.

  • Jurgen Appelo

    Indeed, I’m not bitter. Just having a bit of fun by allowing myself some payback time. 🙂

  • Srikanth

    @Jrurgen: He’s a sub-ordinate and you spelled my name incorrectly.
    But I did that for your name on purpose 🙂

  • Srikanth

    “There are enough jobs in the world, you know.”
    @Omer: Which world are you from? 😛

  • Jurgen Appelo

    Oops, sorry about that!


    Only an asskisser wants to impress the boss. Your work should do that.

  • Hearty Rose

    Wanting to impress your boss means you’ll only get rewarded with MORE WORK!

  • tony

    Agree with Rose. Who needs more work!!!!

  • Jayson

    Every time your boss tell you to do something answer with a serius “Yes I’ll do that right now” and just don’t do it. and when they ask you what happened, Just answered “It got way too busy and I forgot you ask me to do something” repeat. But in any case you want to get fired, don’t get aggressive or show that you are afraid of anything, just be there like a dom, dom..

  • Ahmed

    One more trick, Whenever your manager takes vacation, put him in cc for every email you send and try to send lots of them. May be also all your team can do the same. A lot of trivial non-sens emails with very few important emails that need action or reply from him. The day he comes back from vacation he might find around 100 emails or something waiting him to read a lot. Either he reads everything and be too busy to bug you for a day or two OR, he may not read the important emails and suffer the consequences. 🙂 However, my boss is a really nice guy, i wouldn’t do that to him.

  • Animesh

    Nice one Jurgen. I’m sure they all work like anything. I have also devised some ways to irritate an annoying boss. They can be read at Five innovative ways to irritate your boss
    Just like that…

  • Kangastu

    All I had to do to annoy the boss was turn up 🙁

  • Bobo

    Executing any of these tips will cement your status -within any organization- as that of a moron (or deadwood) and will probably lead to getting yourself fired.
    Not the greatest advice to be giving in these job-scarce times, in my humble opinion.
    I think it is very important to keep your head high and behave at work (and in the world) as a valid and equal entity
    who respects all and fears none.
    If your boss is that bad, it’s probably best to request a transfer. Or, find a new job. It is easier to find a new job when one has a job. Or, if that feels a little like cowardly running; wait the jerk out. If he’s a sucky boss, he probably sucks at a whole lot of other things, so, his time is probably limited, anyway.
    Respectfully submitted.

    • Oceanborne666

      This is intended to be funny, troll.

  • Lizanka

    That passive aggressive tone is probably why your employees are all dicks to you. :O

  • Anonymous Employee

    Or you could use your boss’s email to leave comments on websites like this instead of your own. Hopefully after several different sites he just starts getting a ton of spam.

  • Kavindra Mishra

    You must be one of those worthless, good-for-nothing people who made it to the top by back-stabbing others. A typical Pointy Haired Boss. Each and every line of this truly worthless article is severely offensive.

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