Cover Letters: When They Matter and When They're a Waste of Time

Ask ten people whether cover letters still matter and you'll get two confident answers: "nobody reads them" and "always send one". Both are wrong in the same way. They treat it as a rule, when it's really a judgment about one specific application.

A cover letter costs time, and time is the scarcest thing in a job search. Twenty minutes on a letter is twenty minutes not spent tailoring your resume, which gets read every time. So the useful question isn't whether cover letters matter in general. It's whether this one will be read, and whether it can say something your resume can't.

Why most cover letters go unread

Think about the order things happen in. A recruiter screening a hundred applicants opens the resume first, because it answers the screening question fastest: does this person have the experience the role needs? If the answer is no, the letter never gets opened. If the answer is clearly yes, it often doesn't either, because the decision is already made.

That leaves the middle of the pile, the maybes. This is where a letter gets read, and it's also where most letters waste the chance. They restate the resume in paragraph form, add a line about being passionate and a fast learner, and sign off. The reader learns nothing new, and a letter with nothing new in it might as well not exist.

The same goes for software. As we covered in our post on how ATS systems work, the fields a recruiter searches and filters on are parsed from your resume. A letter won't rescue a resume that never got found.

When a cover letter is worth the time

There are four situations where the letter earns its twenty minutes.

• The posting asks for one. Then it's part of the application. Skipping it tells the reader you either didn't read the posting or didn't care to follow it.
• Your resume raises a question it can't answer. A career change, a gap, a move to a new city, a step down in seniority. If you don't explain it, the reader will supply their own explanation, and it's rarely the generous one.
• A person will read it. Small companies, applications sent straight to a hiring manager, anything that arrives through a referral. When there's no pile, there's no skim.
• The job is about writing or persuading. Communications, sales, client-facing roles, anything involving proposals. Here the letter is a work sample, and it's judged as one.

When to skip it

If the field is optional, your resume already makes the case, and you're applying through a large company's portal alongside hundreds of others, skip it and put the time into the resume. The same applies to quick-apply flows that have no place for a letter. Don't go looking for a way to attach one.

A generic letter in an optional field is worse than no letter. It costs you the time, and it shows the reader that when given space to say something specific, you had nothing.

The exception is the job you actually want. If one of the four situations above applies, "optional" stops being a reason not to write it.

How to write one in twenty minutes

Keep it to three short paragraphs and under 250 words. Each paragraph has one job.

1. Why this role. One specific thing from the posting or the company, and how it connects to work you've done. Not "I was excited to see this opening", which could be sent to anyone.
2. Your proof. Pick the most important requirement in the job description first, then give one or two results that match it. The same rules apply as for resume bullets that prove impact: what you did, and what changed because of it.
3. What the resume can't say. The reason for the career change, the gap, or the move, in one or two plain sentences. State it and stop. Over-explaining makes it sound like a problem.

Then run one test before you send it: swap in a different company's name. If the letter still makes sense, it's generic, and the first paragraph needs rewriting.

If you'd rather not start from a blank page, ResumeLens can generate a first draft from your resume and the job description for you to edit. A draft takes care of the structure. The third paragraph is the one only you can write, so that's where your editing time should go.

The short version

Write the letter when someone asked for it, when a person will read it, when it's a work sample, or when your resume leaves a question hanging. Skip it when none of those apply, and spend the time making the resume harder to say no to.