You're Missing Out If You Don't Write Weekly Digests

Summary

A scheduling faux-pas earlier this year led to the accidental discovery of a best practice that has improved knowledge sharing, discussion, and documentation at thredUP while requiring minimal time investment.

An Odd Handoff

I work on the thredUP merch-science team as Director of Engineering. The merch-science team has always been good about collaboration between product leaders and engineering to ensure that we are fully covered in the case of vacations, leaves of absence, and departures.

This past fall, what would have been a routine handoff was complicated when I scheduled time off that began the day a product leader returned from a week away, giving us zero overlap. thredUP’s marketplace saw huge shifts over the course of the pandemic, and even though she was only gone for a week, there was a fair bit of catch-up to do. I addressed this issue by writing up a digest of everything our team learned about the marketplace that week and the decisions we made based on those learnings. I jokingly titled the document “The Weekly Jenn”, as it was intended only for her, sent her the link, then shelved my laptop for a much-needed respite.

The Revelation

When I returned to work, I was surprised to find many requests for access to this document; it was duplicated and widely shared in my absence. It fostered discussion across teams and with thredUP’s executives. With so many people getting value from “The Weekly Jenn”, what was intended as a one-off morphed into an actual weekly digest. After continuing to write weekly digests for the past quarter and seeing the results, I am convinced it is a best practice more teams should adopt. The rest of this article will detail the problems this digest solves and best practices for writing the digest itself.

Problems Solved

Best Practices

With the above problems in mind, I’ve arrived at a handful of best practices for starting and maintaining a weekly digest:

Thank you to Eddie Salazar and Teague Hopkins for reviewing drafts of this post.