Re: Ask vs. Guess Culture

Published August 24, 2023

I recently read Jean Hsu’s Ask vs guess culture” article as it came across my feed. And honestly, it resonated with me. It was one of those aha!” moments in how I think about things introspectively and the greater context of society, work, and the generation I was born & raised into.

I’d recommend taking the 5 minutes to read the article in full if you haven’t. But if not, that’s OK too.

To recap, ask” culture is when you

ask” for what you want (even if it may seem out of reach) and it’s fine to receive a no

versus guess” culture is when you

guess” indirectly that you’ll receive a yes before asking and it’s rude to receive a no (by putting the other party in that position).

I’ve lived most of my life in the Midwest of the United States and guess culture is significantly more prominent in day-to-day societal existence with the striking exception of work—where ask culture reigns supreme. Ever heard of Midwest nice™?” Having lived in New England and visited the (west) coast it’s a more manageable heuristic to slap the ask culture label there.

And, I think personally, I’m more aligned with guess culture. That said, I think that’s mostly a side effect of my upbringing and the environment(s) I’ve lived in. Unfortunately, it can be difficult to truly think about what I want in a situation because it’s been (unknowingly, and implicitly) ingrained in myself to be more focused on the needs or wants of others.

However, at work, the environment is much more akin with ask culture. Even more so in remote environments: you’re expected, trusted, and compensated for creating some agreed upon output. That’s the value you bring—the entire reason you’re employed. And if there’s something that you need, want, or think is relevant (and important to you + the business) you should bring it up.

For example, I joined a small (fully remote) startup this year. When I joined, there was no benefit attached to those who wanted to leverage coworking spaces e.g. reimbursement. I brought this up with my boss, the CTO, who passed it along to one of the cofounders. After a couple weeks a new benefit was added to give reimbursement1 to employees who opted-in and were utilizing a coworking space for their role. One of my coworkers—who had been there 6+ months prior to me joining—DMed me to share thanks and excitement that their coworking space cost was effectively 100% covered by the company.

I do think I have a slight advantage being inherently guess cultured biased: I’m able to empathize with others who also lean guess. There’s no right or wrong side here, it’s simply a worthwhile notion to keep cognizant of.

  1. Up to $300/mo, which is a modest yet fair amount↩︎

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