To ask or not to ask? I guess not!

Today we touch on ‘Ask’ vs ‘Guess’ culture. I couldn’t trace when exactly this topic was first coined as it’s not a formal academic topic, but I’ve linked a popularly referenced article here.

Art by indie artist Interrobang!?

Key ideas

Essentially, there are two kinds of people, Askers and Guessers. I think this quote explains it best:

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.

Andrea Doderi on Ask Metafilter, 2007 (link)

Personal Reflections

I wanted to pen some thoughts on this subject because it was very illuminating for me when I first discovered this concept. It gave me some new handles to understand people and their behaviours, and I felt it applied to both the home and work contexts.

It’s obvious that I operate in a Guess culture. I usually feel bad when someone goes out of their way for me, to the point that I either don’t ask, or I word my requests very carefully. I believe this may feel annoyed when I feel I’m unable to turn down a request, and it eats into my personal time and space when I’m unprepared for it.

In most of these articles about Askers and Guessers, I find that Guessers are often positioned as the ones who need to fine tune their behaviours to meet that of Askers’. For instance, Burkeman’s article concludes with this advice for Askers: “So say no, and see what happens. Nothing will.” Or take Jonathan Chait’s strong opinion that “Guessers are wrong, and Askers are right. Asking is how you actually determine what the Asker wants and the giver is willing to receive. Guessing culture is a recipe for frustration.”

Is the Guess culture as flaky as it’s set out to be though? Let me point out some ways that such views are incomplete:

  • They forget that Guess culture was a by-product of building a respectful environment. Take the entire premise of etiquette, for example. Complex systems of norms and values (e.g. manners, politeness) help to regulate society and develop good conduct. I think this makes Guess culture very annoying for people to map out sometimes, because it’s difficult to read every cue of what is acceptable or not in every single situation. However, the fundamental idea was always about putting others before oneself, and learning more about how others act and function before imposing our way of thinking on them.
  • Some areas are just out of bounds to Askers. I’m not sure what your opinion of Xia Xue is, but I think she makes a good point in one of her posts about the subject. One of her more pointed examples immediately illustrates how this could be a problem. But a more sanitised example is: Imagine if someone repeatedly asks to borrow money from you, or even a series of favours. You can already see how this simply doesn’t gel with civic mindedness. It’s simply impolite, and can come across as taking advantage of others after a while.
  • They don’t take power imbalances into consideration. Try saying a flat-out “No” to your boss, or to the police. Of course, there are effective ways to communicate your limits, but I do think the onus is on the person with power to give explicit permission for the one being “asked” to state their reasons. It is also about creating a safe space for them to turn down requests or say their side of the story.

That being said, I would like to offer two ways to be better Guessers:

  • Guessers should ultimately remember that clear communication is key to building great relationships. Guessers are sometimes the way they are because of conflict avoidance. Instead of sweeping things under the carpet, Guessers should take steps to convey their expectations, as well as to adequately address and manage conflict. The receiving party (whether Asker or Guesser) should in turn listen, give the other their rightful air time, and seek to understand more than to – well, guess their source of frustration.
  • Guessers could also try to be more accessible. For instance, they could build a habit of taking the initiative to give their time to discuss pertinent issues, or extend a helping hand where it’s needed or requested.

How should Askers respond then? I would like to suggest two ideas:

  • An effective Asker is first an effective Understander. The articles I quoted above seem to imply that Askers are already effective Understanders because they can take “no” for an answer. I would like to push Askers one step further, to ask you to consider why this isn’t always appropriate, or what others may feel and/or think about your requests. If you’re making a big ask, think about how to pose the request in a way that elicits better understanding, such as by explaining your constraints and why you need help. Or perhaps, find the best time to pose your request. If it’s a major topic that needs serious discussion, prime the receiver and request for some time to go through it later in the day.
  • An Asker should also try to be a Giver. Sometimes, it is good to balance out one’s openness in requesting for help by also being proactive with offering help where it’s needed (and again, taking “no” for an answer), such as by doing the chores at home, or returning favours at work. If you’re getting repeated “no”s, find ways to give differently. One thing I’ve learnt is that occasionally buying a small gift for your loved ones, even if it’s not their love language, can still be an effective way of expressing appreciation towards them.

If I might try to summarise my ideas succinctly, an effective Guesser communicates expectations clearly, and an effective Asker operates respectfully.

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