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Boss: I'm getting wildly different estimates for how long it will take to write the software. Dilbert: Based on my experience, I say take the longest estimate and multiply it by three. Boss: Is experience exactly the same as pessimism? Dilbert: Experience is much worse.
Boss: You have to go to a mandatory safety training class right now. Dilbert: Is it safe for me to miss the deadline you gave me for this assignment? Boss: No, you lose either way. Dilbert: Hmm. Maybe I could work all night from home then drive to work exhausted.
Dilbert: I fell asleep at the wheel because I stayed up all night to meet your deadline. I had to work all night because you made me attend a mandatory safety meeting yesterday. But at least I got my work done on time. Boss: I forgot to tell you the meeting got moved to next week.
Man: Can you get that analysis to me by Tuesday? Alice: Yes, if I do it poorly. Alternately, I can do it well and miss your deadline by a week. Man: That gives me no path to success. Alice: Welcome to the world's saddest club.
CEO: Is the software finished as your boss promised me it would be? Dilbert: I forgot to go to the pre-meeting for this meeting, so I'll guess the answer is.. yes? CEO: Okay, keep up the good work! Dilbert: Thanks goodness he doesn't know what the truth even looks like.
Boss: Did you finish the software yet? Dilbert: No, I'm still paying off the technical debt from the last programmer you rushed. Boss: I don't know what that means. Dilbert: Well, that explains a lot.
Boss: I'm giving you another software project to work on at the same time as your main project. Dilbert: That will ruin my flow. It will take too long to reset my brain when I switch between projects. Boss: Have you tried working longer hours without extra pay? Dilbert: Yes I have!