I ran my cover letter through our AI roaster. I've been writing cover letters for 8 years. I thought mine was pretty good.
It was not pretty good.
The original opening (the one I was proud of)
🔥 The Roast: "This cover letter opens with 'I am writing to express my strong interest' — a sentence so formulaic it's basically Lorem Ipsum with ambition. You then spend two sentences explaining what the job posting already says, before finally mentioning something real about yourself in paragraph three. The hiring manager has already moved on."
That stung. And it was correct. I had buried the only interesting thing about me — a specific result — in the third paragraph where nobody would read it.
What was actually broken
- Generic opener that adds zero information
- Paragraph 2 was basically paraphrasing their job posting back at them
- No concrete numbers or specific results until paragraph 3
- Ended with "I look forward to hearing from you" — passive, forgettable
- Total length: 280 words. Should be 150-180.
The rewrite
Lead with the result: "I grew email revenue 40% at [Company] by rebuilding our segmentation from scratch. That's the kind of problem I want to work on at [Company]."
Cut paragraph 2 entirely. Replace with one sentence about why this specific company.
End with an ask: "I'd love 20 minutes — I'm flexible on timing, just send me a few slots."
The rewrite was 140 words. It got a response.
The patterns that get most cover letters roasted
- "I am writing to express my interest" — nobody has ever been hired because of this sentence
- "Passionate", "results-driven", "team player" — these mean nothing without a number attached
- Summarizing the job posting back at them — they wrote it, they know what it says
- Longer than 200 words — brevity is confidence
- "I hope to hear from you" — ask for a specific next step instead
📄 Roast My Cover Letter — Paste yours. Get the same brutal treatment — free preview, $2 full report with specific fixes.
Originally published at conker.tools/blog/roast-my-cover-letter
