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.

2 comments

  • 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