The Case for Cover Letters – REWORK

This week on The REWORK Podcast, host Kimberly Rhodes is joined by Jason Fried to talk about cover letters — what they say about a candidate, how they’re reviewed at 37signals, and why they still matter. Jason shares his take on the value of genuine effort, how AI can either help or hurt your chances, and why hiring should stay a human process.

*Key Takeaways*

00:13 – A cover letter says more about you than your résumé ever could
03:35 – How using AI the right (or wrong) way shows up in applications
06:04 – Why a pre-screening team reads every cover letter first
07:18 – A thoughtful effort is often what gets you to the short list
13:36 – It’s easier than you think to spot procrastination
16:50 – At 37signals, hiring decisions are made by people—not algorithms

*Links and Resources*

“Cover Letters? Yes!” From Jason Fried’s HEY World — https://world.hey.com/jason/cover-letters-yes-25dcdd0c

“When You Review Hundreds of Cover Letters…” LinkedIn post by Jason Fried — https://www.linkedin.com/posts/jason-fried_when-you-review-hundreds-of-cover-letters-activity-7330716611688980484-3HWn?utm_source=share&utm_medium=member_desktop&rcm=ACoAAAFOmhoBb_q4GXRGpaSenRCr6g4eeY_HxpU

Record or upload a video question for Jason and David — https://www.37signals.com/podcastquestion

Get a free Basecamp account at https://www.basecamp.com 

Books by 37signals – https://37signals.com/books

30-day free trial of HEY – https://www.hey.com/

Once. com – https://once.com/

Campfire – https://once.com/campfire

HEY – https://www.hey.com/

The REWORK podcast – https://37signals.com/podcast/

Get some REWORK podcast merch – https://37signals.com/podcast/shop

*Let's be social!*

Twitter/X: https://x.com/37signals
Instagram: https://www.instagram.com/37signalshq/
Newsletter: https://www.basecamp.com/newsletter

Rework is a production of 37signals. You can find show notes and transcripts on our website. 

Leave us a video question at www.37signals.com/podcastquestion or send an email to rework@37signals.com, and we might answer it on a future episode.