The Cover Letter

What is the point...

After spending a month applying for jobs, I have some observations. This may or may not be a thinly veiled request to short circuit the soul-sapping, inefficient and self-confidence crushing process—who’s to say, but don’t let this stop you offering.

It’s surely baffling that after centuries of progress, technology and learning we think the best way to apply for a job is to write a long letter that may or may not be read.

The models of capitalism I was taught said this wouldn’t happen. It’s just too inefficient not to be fixed by the market. But here we are in 2025, being judged on my ability to organise 1000 or so words telling short stories about things I’m claiming to have done in the past for a different job I want to do in the future.

The Economist often writes about how silly it is. (I also agree with their observations on CVs.))

The combined amount of time wasted by people like myself undertaking this bizarre ritual must be staggering. Instead of our skills (assuming I still have some) being usefully deployed, we are hunkered down, saturated with caffeine, trying to stay motivated as we cut and paste the hours away. Maybe the point is just that—that we stuck at—paid our commitment in days spent trying to meet an arbitrary word limit, desperately seeking words to remove and making our verbs sound more electrifying.

If you’re not working but want to, then finding a job is your job. The difference is you work for free and alone. Job seekers quickly realise they face a process problem. If finding a job is a kind of probabilistic theatre, then your odds rise the more you apply for. Your incentive, therefore, is to maximise your chances and the way to do that, is to look for methods of automation, systematisation and repetition.

You’re quickly drawn to focus your effort on scale—break down the process into Adam Smith-sized steps, innovate, find efficiencies and crank out applications with clever tweaks to suggest each job is what you were born to do. Job hunting by mail merge.

If the role you are applying for is about process design, copy editing or innovative uses of AI, then maybe this approach is signalling something to your employer. It’s more likely, though, I am directing a lot of energy at something I don’t want to be good at, save my typing, which is really coming along (55wpm!).

Although yet to be tempted, the obsession with cover letters surely benefits those willing to cheat. If the purpose of a cover letter is to reduce the number of people expressing interest for a role to a number small enough to interview without enduring weeks of misery, then lying seems a rational approach given I have never been asked about something in my cover note at interview, that it’s nowadays unclear if a human will even read it, and of the thousands of cover notes I’ve read as a recruiter, I can remember precisely none (sorry).

Setting aside that cover letters are a terrible idea, there is no agreement on what a cover letter ought to be or do. I’ve been asked to write a one page letter, two pages, up to three pages, no more than 1000 words, 1250 words, 1500 words, with headings, without headings and maybe worst of all, just “a cover letter and CV” leading to nights of angst over which of the menu options should be chosen and what it implies about its author. I’ve been asked to say why I meet the person specification, how I can demonstrate the knowledge for something I’m yet to do and to ensure my style and approach to work is made clear. Not one role has not asked for a cover letter.

This burden of the application process also seems to be being outsourced to the applicant. I often open a job description to find:

• long list of bullet points stating things the person in the role might do, under an arbitrary list of exciting sounding bold headings (usually with pictures of people smiling madly)

• a vague section on “the sort of person we’re looking for” which might be a set of abstract nouns, personality traits or corporate “values”

• a person specification, as if people can be specified, usually a set of abilities or maybe experiences that range from worryingly vague (”experience with people”) to so detailed it’s clearly describing their friend who ought to be promoted next

It’s common, maybe increasingly so with AI, that these sections are muddled, overlapping and inconsistent. If you want to present examples that meet, say, the person specification—which I think is the point—one often needs to first re-write the specification and ideally group it into four or five sections from the long list that’s often presented. I’ve seen many job descriptions with 10 or more “requirements” that need to be met in 1000 words. And to really wind you up, sometimes you can download a friendly “how to write a cover letter”, each with its own cheerful claims to know best.

Unless you have a week to spare, your best bet is to re-write another application until you feel you’ve used enough of the words in the person specification such that the reader might consciously or otherwise feel you’ve paid sufficient attention to merit a chance. If—the horror—you are asked to state your motivation, then you concoct (outsource to AI) a saccharine claim that this specific cause is your lifelong passion. ChatGPT must be laughing at us.

All this confusion must be managed whilst navigating an AI arms race: us job hunters up all night prompt-twerking their applications so that a machine can read and summarise, sometimes via another layer of a recruitment agency—increasingly places to outsource the mountain of recruitment logistics, rather than focus on placing those without a job where they would be happiest.

Perhaps my mistake is applying for jobs. Maybe it’s true most people don’t bother. Maybe many vacancies are performative—to show they tried to bring in new blood. I don’t know—I probably don’t move in the right circles, and I’m definitely a tad jaded. Do suggest what I’m doing wrong.

Hoping at least some employers are looking for the right person, then cover letters cannot be our best idea. Nothing this exhausting can’t be improved. Having willing and (skilled?) labour sitting idle is not helping meet the government’s growth target, either. It’s daft. I don’t want to write it them and you, recruiters, don’t want to read them.

There has to be a better way. I have some ideas—I’m sure you do, too. I’ll leave that for another day, though; I’ve a deadline pending.