Working for a boss who's a dangerous cocktail of arrogance, incompetence, and is self-conscious of it. He's the kind of person who keeps a copy of Steve Jobs' biography and The Design of Everyday Things around his desk. If you ask him a yes-or-no question he responds with, well that depends. And if you ask him to clarify be prepared for a journey through tales of the south, hippie communes, anthropology, and how it all relates to the tragedy of choice and material design. He has an opinion about absolutely everything. He always tries to get the last word. He gives speeches about failure way too much. And if you get on his bad side be prepared for a word-tsunami. You will know it's coming because you can hear him typing furiously from across the office -- the little typing notification flickering on and off in Slack for ten minutes while he composes the final word.
He's the kind of person who will swear he's your friend and has your back. And in one on ones he'll make you feel like people are saying things about you. He'll put you down in front of your direct reports. Will insist on winning an argument even if he's obscenely, incontrovertibly wrong because he's too embarrassed to admit he doesn't know. He once told me that I wasn't using abductive reasoning and if I was smart I would be able to figure it out. I had asked him if we could cut one or two columns from a table in a view so that we could ship on time with a nice user experience after patiently explaining why. And he collected negative feedback from people about my work, without telling me, in order to throw me under a bus at an important meeting with advisors. Then he rolls with my ideas as if they were his own.