> I would love to have later learned that leaders who evaluate opportunities separate from personal attachment are seen as more efficient, better, and selected favorably; that more successful companies are less subject to this sort of political/careerist whimsy.
My experience is that it's the opposite: the more successful the company is, the more prone it is to flights of executive whimsy. At more successful companies, it basically doesn't matter what the executives do, because the company's moat is so big that it can tolerate grotesque mismanagement and still make money. (This is the converse of the old aphorism "When a management with a reputation for brilliance tackles a business with a reputation for bad economics, it is the reputation of the business that remains intact."). Executives seem extremely uncomfortable with the idea that they are being paid tens of millions of dollars and yet nothing they do matters, and so they're intent on leaving their mark. Thus, they cancel all the pet projects of the past management, instill their own ideas, and boldly take the company in a new direction. Except not really, because the fundamental parts of the business that make it work are all handled by people 8 levels down in the org chart whose job functions are considered common sense by everybody and never really up for discussion.
At least, this was my experience at Google, which is perhaps the best money-making machine ever invented and yet is grotesquely mismanaged by mid-level VPs that cancel every promising new product that comes out, only to start their own initiatives that themselves get canceled by their successors.