Bridging the Ask vs Culture Gap at Work

By creating more shared context, aligning around when to ask for help, and helping guess-culture coworkers get clarity on what they want in their careers

Jean Hsu
9 min readAug 26, 2023

In my previous post, I shared the idea of ask vs guess culture, as well as some quick tips for navigating an ask culture workplace as a guess culture person.

If you haven’t already, I recommend reading that post first before continuing with this post that continues the exploration of ask vs guess culture at work.

Despite my efforts to be increasingly ask culture, it’s a bit simplistic to say ask culture is good, and guess culture is bad. The extremes are both exhausting:

  • Extreme ask culture looks like people just asking for more and more, with no regard to how they are perceived, or whether it is appropriate to ask for more. It can be viewed as highly inconsiderate, like asking to order the most expensive item on the menu when you know the person who’s paying is struggling to stay afloat financially.
  • Extreme guess culture is rife with passive hints and people not saying what they want. It requires expert-level context-reading…

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Jean Hsu

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