“Which presidential candidate would you rather have a beer with?” is shorthand for a particular kind of populist gut check. George W. Bush or Al Gore? (Actually Bush doesn’t drink anymore, but you get the point.) It’s a way of asking whose personality seems more accessible. Who would you rather have as your friend?
As a hard alcohol guy and former smoker, Barack Obama actually seems more like my typical bar companion, but that’s beside the point because I’m never going to meet him. It may be comforting to have a personally relatable President, but it’s irrelevant. You’re not electing a Best-Friend-in-Chief.
Here’s a slightly modified version of this question that I do ask myself: “What candidate would you rather be your boss?” A perennial Republican talking point is to imagine America governed as if it were a business, but you don’t have to ask me to imagine that, because I’ve spent a good portion of my adult life working for large corporations in the private sector. “Business” is my default mental model for all organizations. So when I read about a president I naturally imagine them as being one rung above me at Microsoft or IBM or wherever, and then I ask myself: would I respect this guy, or would I be looking for another job?
In order to respect someone in a position of authority I have to have a sense that they are generally competent, on average make more good decisions than bad, are honest with me, and see leadership as a two-way street of obligations in which all parties play equally important roles. I don’t have to like someone to respect them. In fact, in work settings I find this correlation to be pretty weak. I have found myself thinking “I wouldn’t hang out with you, but you are good to work for” and I have also found myself thinking “I find this guy entertaining, but Jesus Christ what a moron.”
Of course “who would you want as your boss?” is also an academic question. I am, for instance, almost certainly not going to end up with a job in the Trump administration. (Though at the rate he’s going through staff members you never know…) I can see how someone could get a kick out of Donald Trump’s coarseness, take it as a middle finger to the Democratic party’s slate of polite upper-class technocrats. (I can also imagine how for many people “one rung above me at Microsoft” is a wholly alien concept.) In that situation you’d want Trump–maybe not as your friend, exactly, but as the blowhard at the end of the bar with a knack for winding people up. Because that can be fun to watch, but it’s not the gut-check you need to be making. A better one is to ask: would you want to work for Donald Trump?