Askers, Guessers, and Personal Finance

A while back, I came across a fascinating article at The Guardian discussing askers and guessers:

This is the “disease to please” – a phrase that doesn’t make grammatical sense, but rhymes, giving it instant pop-psychology cachet. There are certainly profound issues here, of self-esteem, guilt etcetera. But it’s also worth considering whether part of the problem doesn’t originate in a simple misunderstanding between two types of people: Askers and Guessers.


I’m unquestionably a Guesser by nature. For me, the reason is simple to explain: I naturally don’t like it when people make enormous demands of me out of the blue. I tend to avoid further contact with these people. And, thus, I don’t want to make other people feel that way.

In the end, I want to be able to help people when they ask, and I do not like it when people merely view that as an easy thing to milk to get whatever they need from life. An extreme example: a neighbor that I’ve helped with small things in the past leans over a fence and says, “I don’t want to cook supper. Will you make it for me?” I feel as though that person is trying to blatantly take advantage of my willingness to help.

If you flip it to the neighbor’s perspective, it looks like the worst thing that can happen is that I’ll say “no.” But the truth is that the mere presence of such a question makes me tend to like the neighbor less and want to avoid him or her. My perspective is why would that person possibly ask me if he didn’t expect me to go make him dinner, and what kind of person would just expect that out of the blue?

The real difference is the expectation of the question. An Asker doesn’t expect a “yes” answer when they ask – they figure, “why not throw it out there?” A Guesser does expect a “yes” answer when they ask, so they try to keep their queries polite and reasonable and don’t like it when they’re asked unreasonable things.

The problem comes about when Askers assume, by default, that they’re talking to Askers and Guessers assume, by default, that they’re talking to Guessers. An Asker will ask for something big, assuming that the person they’re talking to is also an Asker and will simply answer “no” if that’s not cool and think nothing else of it. A Guesser will rarely ask for anything and when they do, they fairly expect a “yes” response because their requests are infrequent and modest and are usually already clear. Guessers can usually ask things of Askers without too much trouble (usually, the answer is “yes” because the requests are minor) but Askers usually have a lot of trouble asking things of Guessers.

I don’t think there’s anything wrong with being an Asker or a Guesser. I think it’s just a mix of how people are wired and what culture they grew up in. It’s just important to recognize the difference between the two. The article explains it pretty well:

Neither’s “wrong”, but when 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.

My policy for diving through this is simple:

If I’m in a commerce situation or interacting with someone I probably won’t ever meet again, I assume they’re an Asker. In that case, I don’t hesitate to just ask for big things. I’ll haggle on some items. I’ll ask for a big discount. I’ll ask for a “comp” meal at a hotel.

If I’m in a potential long-term social situation where I’ll have to interact with people in the future, I assume they’re a Guesser. I don’t ask for big things until I know the person very well, unless…

If I can, I try to identify Askers from the people I know. That way, I understand where they’re coming from.

So, rewind to my neighbor. When he leans over the fence and asks for dinner, I can realize right off the bat that he’s an Asker and I can tell him “no” quickly if I want without feeling guilty. I also learn that he’s a person I can ask stuff of without hesitation in return.

In short, act like an Asker in commercial situations, act like a Guesser around people you’ll socially interact with over time, and only act like an Asker around people you know who are also Askers. That way, you avoid destroying any social relationships just as they’re beginning to bloom while also being able to haggle and negotiate with the best of them.

You’d be surprised how often this all shows up in personal finance. Take wedding registries, for example. Askers don’t hesitate to say something like “give me cash as a wedding gift,” and other Askers consider that completely fine. People who are Guessers consider it rather rude because you’re making a demand of a gift ungiven. The best solution is to just please both sides of the coin – don’t have a registry at all (and just tell your mother, who people will inevitably call, that you just want cash, putting the onus on the gift-givers to ask) or have a registry that allows you to sift through the received gifts and keep what you actually need after the wedding, returning the rest. In other words, I basically assume that the invitation recipient is a Guesser (either they’ll have to ask with no registry or have choices that are easily returnable with a registry) and that an Asker will ask what I want.

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