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Lesson · Sycophancy × Cover letter

Sycophancy in a cover letter

Why every AI-drafted cover letter sounds like it's interviewing for a job at the company's own marketing department.

SycophancyCover letterWritten by the desk

Sycophancy is the tendency of a language model to agree, flatter and enthuse rather than push back or judge. In a cover letter, this shows up as paragraphs that praise the company indiscriminately — "your innovative approach", "your industry-leading work", "your inspiring mission" — without ever saying anything specific enough to suggest the writer has actually read the company's website.

The reader notices

A hiring manager who reads two hundred cover letters a week can spot generic flattery in a sentence. It tells them the applicant could have sent the same letter to any company on the same list. The honest version doesn't flatter — it shows specific knowledge.

Before

I am incredibly excited to apply for the role at your innovative company. Your industry-leading approach to fintech truly inspires me, and I would be honoured to contribute to your inspiring mission of transforming financial services for everyone.

After

I'm writing about the platform engineer role. I've been following your work since you open-sourced the ledger reconciliation library last March — the design choice to keep balance-as-of queries materialised, rather than computing on read, is the kind of trade-off I want to be making in my own work. I've spent the last two years doing similar things at a smaller scale at Klarna.

The second version doesn't praise the company at all. It demonstrates that the writer knows what the company actually does. That is the real version of "I'm excited about your work".

A test you can run on any letter

Read your cover letter and ask: if I swapped the company name for a competitor's, would the letter still parse? If yes, the letter is sycophantic — the praise attaches to no specific thing. Cut it and replace with one concrete reference to the company's work.

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