The stupidest technical question I have ever been asked is actually more of a design question, but I think it'll appeal to DevRant people.

I had thrown together a logo for a new system that my team was making. The logo was basically a flat, solid circle of our corporate shade of blue, with the name of the product overlaid in Helvetica Light. It looked okay. Ish. Good enough, anyway.

Our junior-most senior manager came to have a look. She was the sort of person who always had to give feedback, on EVERYTHING. Everyone had given this little logo the nod, but she had to stare at it for ages, and then eventually asked:

"I like the text, but can you rotate the circle a few degrees?"

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After an awkward pause I'm pleased to report that she realised her own mistake and we laughed it off, so I was not forced to stand up, point at her, and yell "DURRRRRRRRRR".