Two strategies for getting what you want: asking and guessing

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3 min readMay 14, 2024


👋 Welcome back to the Daily Edition
Issue #75: A philosophy of LLMs, the moments leading up to famous photos, and how to Slack
Harris Sockel

Every once in a while, you come across a perspective that brings aspects of yourself into focus. For me, that’s Jean Hsu’s “Ask vs guess culture,” which starts with a small — but meaningful — distinction: “asking” versus “guessing” as strategies to get what you want.

The idea dates back to (at least) 2007, when MetaFilter user “tangerine” responded to a man who wasn’t sure how to turn down his wife’s friend who asked to stay in their small New York City apartment. (As a NYC resident, I’ve been there!) The entire thread is worth reading; it feels like a precursor to Reddit’s “Am I The Asshole?” community — which, at over 17 million members, has been studied by philosophers as a window into human morality.

Tangerine dives straight into the heart of the conflict:

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.

In other words, the man is a Guesser, and his wife’s friend is an Asker.

As a Guesser myself, I empathize. If you’re a Guesser, Askers may seem impolite and confrontational. If you’re an Asker, Guessers may seem cagey and hard to read.

The most useful part of all this (to me) is how Hsu applies the distinction to work, which tends to lean heavily into Ask Culture. If you’ve ever felt frustrated, misunderstood, or passed over at your job, there’s a chance you’re a Guesser in an Asker’s world. And, as a Guesser myself, this bit of advice was helpful: “Get more comfortable with people saying no to you. If people are not saying no to you, you’re probably still only asking for things that you already know people will say yes to (which is guess culture).”

What else we’re reading

  • Colin Fraser, a data scientist at Meta, investigates why AI systems are so prone to “hallucinations,” or misleading results. Journalists are pretty fixated on the idea that LLMs keep making stuff up, but “after thinking very hard about the nature of hallucination,” Fraser concludes, “I’m personally pretty convinced that it’s a conceptual dead end.” Because an LLM does not have an objective reference point in the real world, everything it produces is technically a “hallucination.”
  • Photographer Lawrence Lazare analyzes the photos taken right before one of the most famous photographs in history: Diane Arbus’ 1962 Child With Toy Hand Grenade in Central Park. (It’s been hailed as “one of the most celebrated photographs in the history of the medium.”) Lazare comes away with a lesson that applies to any art form: There are always a ton of less-good versions created before the final product. Arbus’s famous photo was eighth in a series of less striking versions; taking an iconic photo involves “sensing what might make for a great image, quickly balancing all the elements needed, and then clicking the shutter repeatedly in the hope that one of your frames will result in an image that tells a great story.”

💬 Your daily dose of practical wisdom: about messaging your coworkers

According to Slack’s marketing team, 80% of Fortune 500 companies use the messaging app Slack. Whether you use Slack, Teams, or classic email, Anna Marie Clifton offers five tips for messaging your coworkers if you’re on a remote team. Tip №3, which I practice religiously: Make your messages public by default. If you’re using Slack, default to public channels instead of DMs. Doing so helps build your company’s searchable database of knowledge. (Related fact: Slack stands for “Searchable Log of All Conversation and Knowledge.”)

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Edited and produced by Scott Lamb & Carly Rose Gillis

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