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The Cover Letter That Is Not Generic

ChallengeBeginner25 minAny

Write a cover letter that could only have been written by you, for this job. Tests whether you can force specificity out of a model that defaults hard to platitudes.

Why this one

The test for a cover letter is simple: swap the company name for another and see if it still works. If it does, it says nothing. Almost every AI-generated cover letter fails this test on the first attempt.

0 / 4 steps

Steps

  1. 01Find three specifics about the company

    A recent product decision, something in their engineering blog, a stated value visible in how they actually operate. Do this research yourself — a model asked to research a company will produce plausible generalities.

  2. 02Find three specifics about yourself that connect

    Not "I am a hard worker" but "I spent two months on the same class of problem you described in that post". The connection between the two lists is the entire letter.

  3. 03Write with the substitution test built in

    Give the model both lists and the test itself as a constraint.

    Prompt
    Write a cover letter for [role] at [company].
    
    WHAT I KNOW ABOUT THEM: [your three specifics]
    WHAT I HAVE DONE THAT CONNECTS: [your three specifics]
    
    Hard rules:
    - Every paragraph must reference something from one of the two lists
    - If I swapped the company name for a competitor, the letter must stop making sense
    - No sentence may work equally well for any other applicant
    - 250 words maximum
    - Do not open with "I am writing to apply"
  4. 04Run the substitution test

    Replace the company name with a competitor and read it again. Every sentence that still works is a sentence to cut or rewrite. Usually that is more of the letter than you would like.

You should end up with

A cover letter that fails the substitution test — in the good way.

Done when

  • Swapping the company name makes the letter nonsensical
  • Every paragraph contains a verifiable specific
  • It is under 250 words

If you want to go further

  • Write a second version for a company you would not want to work for and notice how much harder it is

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