Ask vs guess culture

When unreasonable requests are followed up with “but you could have just said no!” Exploring the clashes of ask culture and guess culture, at home and at work.

Jean Hsu
8 min readAug 18


Have you had someone ask you for a favor that seemed unreasonable — a referral you didn’t want to make, a long-term stay at your place, a sizable cash loan? But because they asked, you felt obliged to seriously consider it, to try to meet their request, even if it put you in a space of discomfort? Maybe you carry out the favor, but it sours your relationship, and when it all comes out, that person says, “Well why’d you agree to it? You could have just said no!”

But you feel resentful that that person even put you in a position to have to say, “Sorry we’re a bit busy that week so don’t have space for you to stay with us,” or “I can’t loan you that money at the moment”?

Congratulations, you’ve just encountered a clash between ask culture and guess culture.

The idea of ask vs guess culture was shared online in 2007 by a user tangerine on Metafilter. When I first read it years ago, a lightbulb moment went off, and many frustrations and conflicts I had while growing up made much more sense in this framework.

Despite this idea’s longevity, I find that it’s still a new-to-many and incredibly useful concept to revisit, so here’s a little exploration of ask vs guess culture at home and at work.

Ask culture and guess culture are vastly different in behavior and expectations. Here are some highlights:

Ask culture expectations

  • Ask for what you want, even if it seems out of reach or like a big unreasonable request
  • Take care of your own needs, and others will take care of theirs
  • It’s fine to make requests that people will probably say no to
  • People say yes to requests that they truly feel good about, say no to ones they don’t

Guess culture expectations

  • Only ask for something if you’re already pretty sure the other person will say yes
  • Read an abundance of indirect contextual cues…



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Jean Hsu

VP of Engineering at Range. Previously co-founder of Co Leadership, and engineering at @Medium, Pulse, and Google.