“Be an asker”

Sonnie Bailey

16 December 2022

This article is inspired by another article, “be an asker”, by “Ava”, from her substack bookbear express. I don’t know any more about her, or how I came across the article. I’ll simply refer to her as Ava.

The idea Ava discusses isn’t a new one, but she articulates it well. The central idea stems from the observation that people tend to fall on a spectrum – some people are “guessers” and others are “askers”. In many cases, it pays to be an asker and not a guesser, when for many people the instinct is to be a guesser.

At one extreme, guessers are people who guess what other people want. If they want something from someone, they’ll only answer something if they think the answer will be “yes”. Otherwise, they might assume the answer will be “no” and simply won’t ask. If they do ask, they might do so in an indirect or oblique way.

At the other end of the extreme is the asker. They won’t assume anything. If they want something, they’ll ask, and let the other person make say “yes” or “no”.

I don’t think it’s “right” or “wrong” to be an asker or a guesser. In fact, what’s appropriate depends on context. As Ava explains:

“I don’t mean [to encourage being an “asker”] in the sense of you should harass people. Asking in the wrong way can be bad, and asking when someone’s given you a firm no can be very very bad, so there’s some level of emotional sensitivity required here.”

However, I think this article resonated with me because I tend to be a guesser, and in most cases would benefit from being more of an asker. Less selfishly, I think other people in my life would benefit if I was more of an asker, and I think many people could be more ask-ey.

Why ask

Guessing is guessing! Your guesses are probably wrong more often than you think!

At the end of the day, we don’t know anyone with full fidelity. The truth is, I don’t know myself entirely. It sometimes surprises me what I say “yes” or “no” to.

No matter how well you know someone, you don’t have a complete model of their thoughts and values in your own mind. Quite often, the closest people in my life surprise me.

If you’re inclined to be a guesser, consider making a note of how you assume people will answer, and treating that as a hypothesis. See how closely your hypotheses match reality. (Better yet, give percentage estimates and see how well-calibrated your assumptions are! Perhaps, by being an asker, you might become a better guesser informed by real-world feedback!)

It can save you time

At a very simple level, “asking is good because it saves you time. It’s amazing to me how many people find roundabout ways to lightly hint at what they want when they probably could’ve saved themselves hours and hours by just asking directly”.

The rewards outweigh the costs (in expectation)

“most of the time you are not going to be penalized for asking. [By failing to ask y]ou penalize yourself”

Living a fulfilling life

Ava talks simply about being an asker as being related to “living a fulfilling life”. She shares her belief that “a lot of people who don’t ask for what they want explicitly end up resenting themselves and resenting the world”, and suggests that “if you’re able to stop punishing yourself for asserting your needs, something very important changes. You become capable of advocating for yourself.

How to approach it

Ask lots of people one question rather than one question a lot to one person

“It is generally way more effective to ask a lot of different people than to ask one person many times.”

“If it’s very easy for the other person to say no (zero cost to them) and you’ll probably never see them again, ask whatever you want (politely)”

Be explicit

Sometimes, it’s about being explicit. As Ava says, “You may think your hints are super obvious, but most people are not paying as much attention to you as you think they are.

Be okay with people saying “no”

“Never get upset at someone for saying no. You don’t ‘deserve’ an answer. The truth is, people who don’t know you don’t owe anything to you, and even people who know you really well are free to prioritize themselves

In describing her friends who are good at asking, she notes that “they’re not coming at it from a needy place—they’re genuinely super chill and are fine with hearing a no; they’re also good at making people feel like it’s safe to say no to them”. She acknowledges that “it’s really hard to fake security when you’re not secure, and asking just works a lot better if you’re coming from a secure place”.

One way that I’ve been able to frame this to myself and others is to use the motto that an unplanted seed never grows.

Another is to admit to asking a “cheeky question” (which is how I gained most of my testimonials for Fairhaven Wealth – “I have a cheeky question! And there is no pressure or obligation at all”…)

Asking is a skill

One other thing I’ll add is that asking in the right way is a skill. There are ways to be more or less persuasive when asking.

Another skill – which I’d argue is just as important, especially in situations involving power disparities – relates to providing people with an out. Sometimes it’s not easy to say “no” when someone asks you something. In fact, sometimes it’s hard. If you’re going to be an asker, then you need to be okay with people saying no, and you need to ask in ways that make this clear.

Is there something you’ve been meaning to ask someone? Instead of guessing at their answer, wouldn’t it be better to ask them in a thoughtful, tactful way?

An unplanted seed never grows…


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