← All issues

The Compound Years · Issue #17 · October 2026

What I look for in a cover letter

Two paragraphs, one real signal -- and most cover letters never get to it.

01The experiment

The best cover letter advice I know is Derek Sivers’: say the thing only you could have written.

Almost every cover letter is the same letter. The same adjectives, the same enthusiasm for a company the writer learned about an hour ago. The ones that land describe a specific thing the person actually did, in the voice they actually speak in. That is hard to fake and quick to read, which is the whole advantage.

02The lesson

Writing in your own voice is a discipline built by writing -- there is no shortcut.

You can read a hundred guides on cover letters and still produce generic ones. The dataset that fixes it is the one you build by drafting, sending, getting ignored, and rewriting. The candidates who sound like themselves on the page almost always wrote a lot before that letter landed.

03The founder

Patty McCord wrote the Netflix Culture Deck around specific signals over generic credentials.

McCord and the Netflix team built a hiring culture where ”fully formed adult” beat ”ten years at a brand name.” The Culture Deck -- viewed over twenty million times -- argued that the signal you want is evidence of judgement under real constraints, written in the candidate’s actual voice.

04The mindset

The discipline of one specific signal beats the temptation of ten generic ones.

When I am writing anything that has to do work -- a cover letter, a pitch, a homepage -- I try to land one specific signal well. The temptation is to stack five at half strength. The habit I am building is to cut four and let the one breathe.

05The question

What is the one specific signal you would put in a cover letter for the job you actually want?

Hit reply and tell me. I read every one.


Forward to one person who is writing a cover letter this week.

-- David