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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