Cover Letters: The Good, the Bad, and the Ugly

Recently I got an earful (or, more accurately, an inbox full) from some employers about the fine art of cover letters - mostly about what not to do. I'll paste in a sample below.

This is a good opportunity to remind my twenty-something crowd that there are often generational dynamics at work when you submit cover letters, to Gen Xers in particular. Overwhelmingly, my Gen X contacts recoil from what they perceive as extreme self-congratulation in Gen Y cover letters -- something to keep in mind when you're writing for a particular audience. Things that might fly with your own age group, or your boomer parents, or admissions officers don't necessarily go over well with everybody.

The other common theme is that long cover letters go straight into the trash, so keep your cover letters short and sweet.

Reactions? Advice? Anecdotes? Please share!

  • So I am trying to staff my new office and am reviewing a few hundred resumes. Painful on many levels. Who the *hell* taught people to write cover letters that include phrases like "My analytic ability is keen" or "my written and oral skills are exceptional" or "I am confident you will find my communication skills outstanding" or, my favorite, "I am tomorrow's strategic executive."???? Literally every other letter includes this crap. Anna, save these people.
  • I've been doing interviews for internship positions for the past few weeks. I've noticed how little I pay attention to the cover letters (I skim...I'm talking 30 seconds, tops). If the cover letter takes up the entire page, I almost never read it (I just look at the length and say, "too long").
  • I've now read or skimmed a few hundred cover letters in the last 48 hrs and have learned nothing positive from a single one. Cleverness comes off as defensiveness and confidence as boastfulness. I don't even think the negative impressions I'm left with are necessarily deserved, and I've decided to give some interviews in spite of the letters. People need to shut up.
  • They need to use extremely conventional resume formatting because I refuse to look at "Skill Profile" sections and resumes divided into quadrants and school listings that fail to show me grad dates. I shudder to think that the cover letters for my own 20 year old internship applications could even conceivably still exist somewhere. I committed all these sins in spades.
  • I think cover letters should be extremely straightforward, repeat little that is in the resume, and never try to be boastful or cute. I know this is tougher for recent college grads - they presumably need to show why they want a particular job. But then just say that. Shut up about supposed attributes. If they want to be clever (and they shouldn't) then save it for the resume in the extracurriculars.
  • I can think of a lot of scenarios when a cover letter is essential -- esp. when you are explaining a non-traditional path or a not-obvious transition. I just haven't seen many done well.
  • First rule of cover letters is: do no harm. They can help, but rarely do, and the assumption in some professions is that the decision makers never see/look at the cover letter anyway, just the resume. So the goal is to write something that doesn't end up in your file with a highlighted part and a note that says "what a dolt!"
  • I got 180 applications for the last position I had - for a job that includes lots of writing and even more editing. More than half the apps got thrown out based on the cover letter alone. Not just bad writing, but misspellings, grammar problems, proofreading errors, and one reference to "The Lord led me to you [sic] job decsripton [sic]." You've got to wonder what they thought they were going to accomplish.


Former Dean of Admissions at the University of Chicago Law School and a recovering lawyer, Anna Ivey founded Ivey Consulting to help college, law school, and MBA applicants navigate the admissions process. Read more admissions tips in The Ivey Guide to Law School Admissions, recently updated and available as an e-book. Follow Anna on Twitter (@annaivey).