The smallish corner of the internet I pay attention to is abuzz with the Asker vs. Guesser question. I first saw reference to it by Jon Chait, who cites Oliver Burkeman’s pick up of a “cult status” achieving comment by Andrea Donderi (AKA “tangerine”). Burkeman writes,
We are raised, the theory runs, in one of two cultures. In Ask culture, people grow up believing they can ask for anything – a favour, a pay rise– fully realising the answer may be no. In Guess culture, by contrast, you avoid “putting a request into words unless you’re pretty sure the answer will be yes… A key skill is putting out delicate feelers. If you do this with enough subtlety, you won’t have to make the request directly; you’ll get an offer. Even then, the offer may be genuine or pro forma; it takes yet more skill and delicacy to discern whether you should accept.
[W]hen an Asker meets a Guesser, unpleasantness results. An Asker won’t think it’s rude to request two weeks in your spare room, but a Guess culture person will hear it as presumptuous and resent the agony involved in saying no. Your boss, asking for a project to be finished early, may be an overdemanding boor – or just an Asker, who’s assuming you might decline. If you’re a Guesser, you’ll hear it as an expectation. This is a spectrum, not a dichotomy, and it explains cross-cultural awkwardnesses, too: Brits and Americans get discombobulated doing business in Japan, because it’s a Guess culture, yet experience Russians as rude, because they’re diehard Askers.
Now we learn that Chait thinks Askers are right and Guessers wrong. Tyler Cowen is an “[A]sker when it comes to information, but a [G]uesser when it comes to making demands.” And Kevin Drum is an Asker wannabe Guesser.
The problem with assuming one way is better than another is that it ignores the obvious temporal heterogeneity in preferences. The “requester” (whether of Asker or Guesser type) is in more in need of a “yes” (or “no”) response from the “requestee” (again, of either type) at some times than others. Likewise, a requestee is more likely to say “yes” (or “no”) at some times than at others. The more you care about the outcome the more important it is to know your counterpart and time your interaction accordingly. It also matters if your counterpart is unique or if your request can be satisfied by many others.
Therefore, it is perfectly sensible to be an Asker for some things at some times and a Guesser for other things (or even the same things) at another. Cowen’s response most embodies this principle and Chait’s lack of flexibility is the antithesis.
As for me, I’m the opposite of Drum and tend toward the Asker type but think being a Guesser is sometimes better. Basically, I can be impulsive and blunt. So, I’m learning to be more of a Guesser when situations warrant it.