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
• “When You Review Hundreds of Cover Letters…” LinkedIn post by Jason Fried
• Record or upload a video question for Jason and David
• Get Basecamp for free at Basecamp.com
• Books by 37signals
• HEY World | HEY
• REWORK podcast merch
• The REWORK podcast
• The Rework Podcast on YouTube
• The 37signals Dev Blog
• 37signals on YouTube
• @37signals on X