An Asker and a Guesser walk into a bar...

An Asker and a Guesser walk into a bar. The Guesser tells the bartender, "One beer, please." The Asker asks the Guesser, "And what will you have?"

A debate is raging in the blogosphere thanks to this column by Oliver Burkeman. He picked up on a thread by this woman, which I'm excerpting here:

In some families, you grow up with the expectation that it's OK to ask for anything at all, but you gotta realize you might get no for an answer. This is Ask Culture.


In Guess Culture, you avoid putting a request into words unless you're pretty sure the answer will be yes. Guess Culture depends on a tight net of shared expectations. A key skill is putting out delicate feelers. If you do this with enough subtlety, you won't even 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.


All kinds of problems spring up around the edges. If you're a Guess Culture person -- and you obviously are -- then unwelcome requests from Ask Culture people seem presumptuous and out of line, and you're likely to feel angry, uncomfortable, and manipulated.


If you're an Ask Culture person, Guess Culture behavior can seem incomprehensible, inconsistent, and rife with passive aggression.

Burkeman finds the situation not entirely hopeless:

Self-help seeks to make us all Askers, training us to both ask and refuse with relish; the mediation expert William Ury recommends memorising "anchor phrases" such as "that doesn't work for me". But Guessers can take solace in logic: in many social situations (though perhaps not at work) the very fact that you're receiving an anxiety-inducing request is proof the person asking is an Asker. He or she is half-expecting you'll say no, and has no inkling of the torture you're experiencing. So say no, and see what happens. Nothing will.

The debate is now making the rounds in the Atlantic, Mother Jones, The New Republic, and more. Are you an Asker or a Guesser? Do you ask for things when you need/want them, or do you only make requests when you're sure they won't be imposing on the other party and the other party will in fact acquiesce?

And how do you deal with people of the other type?

Here is where I stand:

When push comes to shove, I am certainly an Asker. When in doubt, I will ask. When I was asking daily, if thought the answer might be no, at times I changed my approach in order get what I wanted, but I rarely shied away. In fact, asking daily allowed me to gain an intellectual and emotional distance from the outcome, because even if I got a "no," it was all for the good of the experiment.

After the year of daily asking -- and doubtless because of it -- I kept that attitude of "who cares if I fail!? At least I tried and settled the uncertainty by articulating my request."

Now that I'm more selective in my asking -- I don't do it daily, and the stakes are often higher -- I aspire to be an Asker who knows when to guess and a Guesser who knows when to ask. I want to use both strategies as precisely that -- strategies!

So many of the voices blogging about this are framing the debate as Askers vs Guessers, as if these were some immutable categories people were dropped into as infants by some divine toga wearing shepherd. Certainly, some people are stuck in one of those modes, but the optimal -- and perfectly feasible -- strategy is to be flexible and use both asking and guessing, as verbs, that is, to your advantage. So I encourage you, dear reader, to step back and consider this instead: To get the best outcome, when should I ask, and when should I guess?

In the next post, I'll offer 5 ways to refine both of these strategies.

But first, what's your take: Do you ask or guess? Do you wish you did more of one or the other?