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

• Visibility and Transparency
  The merch-science team manages thredUP’s two sided marketplace and hence has wide-ranging responsibilities that affect most other teams in some way. This makes disseminating learning and decision making problematic, but I think this problem is largely resolved by writing up major happenings.
• Discussion
  Another benefit is that this document is a great way to foster discussion. The Weekly is a Google doc open for comments to everyone in the company, and in practice, people make great use of comments, asking and answering questions, pointing out opportunities for collaboration, highlighting areas for follow-up, and celebrating wins.
• Documentation
  Lastly, this document is turning into a piece of our institutional memory and knowledge management. Institutional memory in practice usually means “the memories of the longest tenured employees”, but this is less than ideal, even at a company like thredUP with many long-tenured folks. Some issues and questions tend to recur, and remembering what decisions were made or which experiments succeeded or failed is often insufficient. The context surrounding what decisions we made can be as critical to understand as the decisions themselves, and in a growing company facing shifting consumer behavior, context can change very quickly. In addition to helping future decisions, I also see this document as a great onboarding resource as we continue to grow our merch-science team.

Best Practices

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

• Set reasonable expectations
  I made it clear from the outset, especially to executives, to expect a low-polish document. We’re all busy enough and I doubt maintaining such a document is sustainable if it’s tacking another four hours of work on to your week.
• Back it up with data
  Include data, graphs, and charts and link to sources. This provides further transparency to everyone viewing the document and will save a lot of time in the future should you find yourself revisiting problems and decisions discussed in the digest.
• Keep it simple
  Make the writing as accessible to the widest group of people at your company that you reasonably can. Tailoring content to your audience is a critical skill for engineering leadership; I’ve found it beneficial having another vehicle to refine this skill.
• Make it a habit
  Share the document in the same place every week with a short summary of this week’s topics. We use a public, well-trafficked Slack channel.

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