Proposal Work:
Me: "I need the client logos for the client pages."
Boss: "They're in this PowerPoint slideshow." (in the slides they are icons the size of a peanut)
Me: "Can't you have them email them to us in high-resolution format?"
Boss: "No. Use these." I use them. They look like lego blocks. Boss hates them.
Boss: "These look like shit."
Me: "I told you yesterday that they would."
Boss: "Fix them."
Me: "Can't they send them to us in the original format?"
Boss: "I don't want to have to ask them for this again. Can't you do something else?"
Me: "Uh, I can redraw them in Photoshop."
Boss: "How long will that take?" (bear in mind I was getting double time for doing this)
Me: "A week, at least."
Boss: "Fine. As long as I don't have to call them back."
40 hours of overtime to save the boss a phone call to a person he was calling 10-12 times a day to get copies of logos that the companies had on file on a project that they were teaming with us to bid on based partially on our technical expertise.