March 11th, 2025

What an insightful observation, you get to wear “the hat”

In the past, I have noted that teams have used physical objects as a reminder or used them as an honor, or as a form of shame.

I recently learned that this tradition exists in Microsoft outside the software development world. At least in one part of the Finance department, they had a hat that had the word “Hat” printed on it. If you said something totally obvious in a meeting, you had to wear “the hat”.

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Raymond has been involved in the evolution of Windows for more than 30 years. In 2003, he began a Web site known as The Old New Thing which has grown in popularity far beyond his wildest imagination, a development which still gives him the heebie-jeebies. The Web site spawned a book, coincidentally also titled The Old New Thing (Addison Wesley 2007). He occasionally appears on the Windows Dev Docs Twitter account to tell stories which convey no useful information.

9 comments

  • Richard Thompson 3 days ago

    Basically, a sticker hides damage.
    A crack or other damage underneath the sticker may not be visible, so you think you’ve got a good hat – but you don’t.

  • Mike Morrison 2 weeks ago

    What is the point of shaming a team member? Wouldn’t it be more productive to sit down with someone who made a substantial mistake and work out what happened and why?

    Does this practice continue with Windows dev teams in the present day?

    Also, I agree with Yuri that what’s “Totally Obvious” to one person is completely new to another. It sounds like The Hat was punishing people who merely had a different perspective from others, not even one who made a consequential mistake, like breaking a milestone build, for example.

    • Raymond ChenMicrosoft employee Author 2 weeks ago

      I think it is done more as a joke for “duh” statements like “The ground tends to be more wet on rainy days.” For finance talk, I’m imagining something like “If you increase spending, it tends to cost more.” You say something and then realize it was a tautology and you get The Hat.

  • Lyubomir Lyubomirov 2 weeks ago

    I’m wearing the hat, by default.

  • Jason Harrison

    We had a rubber chicken for breaking the build. But it was a punk rock rubber chicken so the shame was greatly diminished.

  • Richard Thompson 2 weeks ago

    It is a longstanding tradition in some circles that the crew boss has deely bobbers on their hardhat.

    It makes them easy to see across the site, they’re easily transferred when a new boss takes over the shift, and doesn’t affect the integrity of the hardhat (unlike stickers, for example).
    If it also helps avoid them getting too big for their boots, that’s merely a tiny side effect.

    • Brandon Hood

      At the risk of wearing The Hat… Could you explain to a layman how a sticker compromises a hardhat’s integrity?

  • Yuri Khan

    My experience is that what is Totally Obvious differs between people. It it better to risk wearing the Hat than risk withholding critical insight.

  • Matthew van Eerde (^_^)Microsoft employee

    I would end up with this hat in every meeting