I had conversations like this many times... I once worked for a company named Stac Electronics. At one point the company hired a new CEO (J.T., for insiders). Read today's Dilbert strip:
This brought back instant memories, and for me, some laughter. That CEO – who was running a software company – had technical expertise that was over-matched by any randomly-selected decomposing aardvark. I was, at the time, the company's chief technical officer. After my first few attempts to have a meaningful conversation with him (my boss!) about anything I did, I gave up. Then I started entertaining myself at his expense, by trying to see just how nonsensical a conversation I could have without him picking up on it.
I never found the limit. He resigned (for other reasons) before he had any clue what I was doing...
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