Step 4: How to write the perfect cover letter
Since we’re among friends here, we can call spade a spade. I’ll even go first:
Cover letters are silly. They are old-fashioned and stupid, and they don’t make any sense. You always sound like you’re begging for the job. You also somehow sound like you would literally rather set yourself on fire than get the job. How is it possible to sound this arrogant and also like you have no confidence at exactly the same time? Why must we be forced to cobble together this awkwardly regurgitated poetry-slam performance-art piece? Oh, and a 2017 #ENTRYLEVELBOSS survey found that nearly half of hiring managers admit to not even reading them. This is torture and it’s pointless and it’s stupid and we hate them.
Go ahead, let it out, release a primal scream or something.
You good? Cool, because you still have to write one.
The good, the bad, the ugly
I used to think that if I could craft the most perfect cover letter on the planet, I would be set for life. I would convince companies to fall at my feet, charmed by my desire to #hustle and #learn thanks to this #exciting #opportunity. Yes, yes, I was one cover letter away from becoming the most hireable woman in the world. Oddly, this turned out not to be the case. As we covered in Part 1, the digitisation of the hiring process (see page 25) left us with some peculiar artefacts of the past — and cover letters are always my favourite example whenever I get the chance to point out glitches in the Matrix.
Think about the phrase for a minute: cover letter. Similar to rewind or phone call, the words are just haphazard leftovers from the past. From a simpler time, when an employer would put a classifieds ad in the local newspaper and receive CVs in the physical mail. The cover letter would have literally been sitting right on top, covering the CV. Physically covering it. Because they were, you know, printed on real sheets of paper. In that day and age — which, by the way, I never lived through and yet I, too, was told to put an employer’s postal address at the top of the page — a cover letter was your one big moment. It was your only chance.
Imagine the employment world before LinkedIn, Facebook, Twitter, or Google searches. There was no one-click way for a potential employer to stalk you or gain context about you beyond what you yourself had provided. You just read about that job posting in the paper, sent in an application, and waited for a reply — probably by owl or something. The only thing anyone would ever know about you were those words written right there on the page (which really explains the entire plotline of Leonardo di Caprio and Tom Hanks’ 2002 masterpiece, Catch Me If You Can, if you think about it).
Dear Sir,
I hope this physical piece of paper finds you in good health. I am writing to enquire about the recent advertisement for the role of experienced backgammon player, which I saw listed in the Old-Fashioned Newspaper on the 3rd of February, 1923. I have ten years of experience playing the game of backgammon and have won 87 of my last 144 matches. If you would be so kind as to write me back promptly, I would take the train to the big city in one fortnight’s time so that I might discuss the specifications of this role with you in person.
In 2017, the #ENTRYLEVELBOSS team surveyed 200 hiring managers and recruiters across the United States and United Kingdom about how they filter candidates and make final decisions about who gets the job. One of our questions was, ‘What are you looking for in a cover letter that you can’t find in a CV?’ More than 70% of survey responses referenced personalisation and a candidate’s motivation for joining the company.
Not every role needs a great writer, and hiring managers understand that. They aren’t looking for anything magical, they just want context about who you are and why you’ve decided to apply for the job. Why do you want to work for this team? Why? It’s not an exam, it’s just an honest question that you should be able to answer. Why spend all your waking hours working on this project, selling this kind of product, with these people?
Cover letters are a passionate topic for both hiring managers and job seekers alike — everyone’s got something to say. During the many conversations I had while writing this book, two specific comments stuck with me.
The first is this beautiful rant from Danae, an American engineer turned chief marketing officer based in Edinburgh. I think she speaks on behalf of hiring managers everywhere with her ten pieces of sage wisdom for job applicants. In her own words:
For me, it’s ALL about the cover letter. It’s my secret weapon for hiring amazing people. Cover letters give me context. I view it as your number one competitive advantage in a job application. Here are my tips:
On the job seeker side, I read dozens of compelling cover letters; I’ve heard a bunch of success stories, and listened to many tales of cover letters gone wrong. No one, however, put it as beautifully as Julianne from California. Three separate times to date, Julianne has been able to explain her way into roles thanks, in no small part, to three killer cover letters. In her own words:
My first job out of university was teaching hands-on environmental science to children for a non-profit programme. Unlike everyone else in the same position, I had no background in education or environmental science. Instead, I had degrees in African History and Physical Anthropology. But I wrote a thoughtfully constructed cover letter highlighting personal attributes that I believed were relevant to the position: my public speaking and communication abilities, my passion for the environment, and my interest in and understanding of biology (shout out to physical anthro!). I was invited to interview for the position and was offered the job the next day.
I was equally ‘unqualified’ for my second job: working as a support counsellor for at-risk foster teenage girls. The position called for experience in social work, of which I had none. Again, I wrote a thoughtful cover letter emphasising my work with kids (from the previous job) as well as my empathy and compassion. I was invited to interview and again offered the job.
My third job had nothing to do with education, social work, African history, or anthropology. It was a project manager position at a marketing agency. Once again, I pulled relevant details from my academic and professional background and wove them together into a compelling cover letter that led to an interview. After several (probably annoying) follow-up emails, I was offered the position. I have worked in marketing ever since.
Of course, my killer cover letters alone weren’t what got me these jobs. But my interview skills and persistence wouldn’t have counted for anything if my cover letters hadn’t got me in the door.
I found employment in education, social work, and marketing, all with two seemingly totally unrelated degrees. But the thing is, I don’t actually think my degrees were totally unrelated. Both History and Anthropology require excellent communication skills. Both also centre on a deep understanding of humans. And it turns out communication and understanding people are integral to education, social work, and marketing.
For example, when I graduated, all I had on my CV under work history was seven years working at surfing shops. I also decided to include the one summer in high school when I gave surfing lessons to kids. So when I described my work history on my CV for the environmental education position I made sure to emphasise my (very informal) teaching experience: that as a supervisor I’d trained X number of sales associates and X number of new supervisors, and as a surf instructor I’d taught kids how to surf. It wasn’t much compared to other applicants who had been teaching assistants in schools for years, but it was enough to show that I was able to teach someone something. I figured it was better than nothing. And, hey, combined with a killer cover letter, it worked!
Every job since then, I have done the same thing. When I applied for the support counsellor position and all I had on my CV were surfing shops and environmental education, I focused on the fact that 25% of the students I taught were considered ‘at-risk’. Sure, it was only a quarter of the students I worked with, but it would have been foolish of me to leave ‘at-risk’ off of my CV when applying for a position working with ‘at-risk’ foster teenage girls.
When I applied for the project manager position, I knew that my experience selling surfboards, teaching kids about birds, and working with troubled foster youth wouldn’t be wildly compelling. I focused on other aspects of those jobs instead. When I described my time working in surfing shops, I emphasised the fact that I was promoted from sales associate to supervisor in just two months to underscore my strong work ethic and ability to learn quickly. When I described my time teaching, I highlighted how I was the only one in my cohort to be invited to become a lead instructor and how I was asked to write articles for their monthly newsletter once they realised this woman can write. And when I described my work with the foster girls, I focused on logistics: tracking stipend budgets for each of my clients, organising home visits with a wide cast of characters (social workers, lawyers, foster parents, biological parents, IEP mentors, etc.), and developing and implementing individualised incentive plans.
I’ve never cared much about titles because focusing too much on titles can be very limiting. Just because I had never been a teacher didn’t mean I had never taught someone. Just because I had never been a support counsellor didn’t mean I couldn’t support someone. And just because I had never been a project manager didn’t mean I couldn’t manage a project.
Long story short: you might be better equipped for a new field than you realise, you just need to get creative and find a way to make what you’ve got work for you.
The templates
I’m going to walk you through two different cover letters formats. Both of these formats are based word for word on real cover letters from my past that have successfully got me an interview at some point in my life. That doesn’t mean, in the slightest, that these are the only two right answers — far from it. Every company will have its own preferences. Every cover letter you write will be different. Every situation will be unique. It will be entirely up to you to tell your story, but I can help you figure out where to start.
Cover Letter 1
Hi [Company Name],
I’m Alexa: a copywriter who works with product teams. I’ve collaborated with UX designers and engineers at consumer-facing tech companies like [Client/Past Employer 1], [Client/Past Employer 2], and [Client/Past Employer 3] — and I’m hoping that [Company Name] is up next.
A San Diego native, I’ve spent the last three years working alongside the best and brightest in Berlin tech. I’ll be moving to London in January 2017 thanks to TechCity UK’s Exceptional Talent Visa Scheme.
I’ve been watching [Company Name] from afar for the last few years and I really dig your style. You’re leading the market in [thing you have observed the company is good at]. I can see the team’s dedication to [something even more specific]. Your [specific detail about their product, their marketing, their business model] is a clear testament to [a value that you also value]. I love the way you [cite a specific example you’ve noticed, something to demonstrate that you are already thinking critically about where you could be helpful]. I worked on [briefly mention a project that shows you know how to handle this kind of thing] for six months last year.
I’m excited about the opportunity to join your team as a [role], because I know that I could help you continue to [specific task/project/thing you’d like to help the company with]. I’m fascinated by figuring out how to [cite a problem you see company facing], and I know that my experience in [skill the position requires] and [other skill the position requires] could help you solve that problem. Looking forward to chatting more soon.
Warmly,
Alexa
PS: [Brief observation about being a customer of the company (‘I love that new product!’) or comment about a recent press piece (‘Congrats on the new partnership with So-and-So!’)]
Casual language: informal vs. unprofessional
The first thing you’ll notice in the above cover letter is that the tone is friendly, casual, and warm.
While there are certain industries (finance and law come to mind) where a formal tone is still appreciated, the vast majority of work environments have begun to move on. The formal tone doesn’t feel natural when you try to write that way — and I promise that it doesn’t feel natural to the ear of the 35-year-old recruiter who’s filtering through applications on the other side of the screen, either. Write down ‘To Whom It May Concern’ on a piece of paper and burn it over a candle tonight, if you feel like it.
You and I both know all the clichés about millennials and Generation Z: we’re entitled, we’re arrogant, we don’t want to work hard, we’re soft, we can’t take feedback. Look, there’s a huge difference between being friendly and being edgy — and it could lose you the job if you get it wrong. A cover letter, for example, is probably not the right place for shock factor. It is certainly not the right place to call your new co-worker, a person whom you likely haven’t met before, a pet name like ‘babe’ or ‘love’.
Think of your new professional voice as a slow shift from 1970s business attire into 2020s business attire. You’ve invented an updated, modern version of a timeless classic. You are young, fresh, sharp talent — and you get to sound like it. The sign-off I use (‘Warmly’) is a good example of striking the right balance in tone. (I also like ‘Cheers’ and ‘Thanks’ and ‘Speak soon’, to give you a couple of other ideas!) It’s friendly, modern, professional, confident, but still professional-sounding. Not too sassy, not too stuffy, just right.
First, introduce yourself
Cover Letter 1 offers a great example of the most precious, most important, most helpful, most job-getting copywriting tip I can ever give you. It’s something you should do on cover letters and on LinkedIn and in networking emails alike: introduce yourself.
Imagine how a cover letter would sound if it was read out loud in real life. Without an introduction, you quickly become some stranger with a name tag who’s wandering up to people on the streets and asking for a job. Bizarre. Rude, even. Because how do all conversations start? With introductions. With a name. Introductions offer you a way to start building rapport with your future colleagues immediately, simply by translating basic offline manners onto the page.
People like classifying each other. I haven’t lived in San Diego since I was 18 years old. Regardless, the words ‘originally from San Diego’ tumble out of my own mouth multiple times a week. It’s human instinct to want to know where somebody’s from, where they live now, and why they’re approaching you. Think back to all those scenes in Game of Thrones in which Daenerys announces her own presence — with authority and eye contact — by saying that she’s ‘of the House Targaryen, First of Her Name, the Unburnt, Queen of the Andals and the First Men, Khaleesi of the Great Grass Sea, Breaker of Chains, and Mother of Dragons’. By giving a quick synopsis of her home town and CV, she provides her new allies and enemies with enough context to do the instinctive human work of assessing danger, skill, trustworthiness, and potential. This is your opening paragraph — people need context before they can care about anything else you’re going to say.
Harvard social psychologist Amy Cuddy explains the two dimensions people intuitively scan for during the first impression moment:
When we form a first impression of another person it’s not a single impression — we’re really forming two. We’re judging how warm and trustworthy the person is, and that’s by trying to answer the question, ‘What are this person’s intentions towards me?’ And we’re also asking ourselves, ‘How strong and competent is this person?’ That’s really about whether or not they’re capable of enacting their intentions. Research shows that these two trait dimensions account for 80 to 90 percent of an overall first impression, and that holds true across cultures.
Leverage human instinct and introduce yourself.
Start with a quick recap, Daenerys-style, that tells your future employer who you are and what you’re about. This is the opposite of the advice I learned from my own university career advisors. This old-school approach might look familiar to you …
Throw it out. Don’t do this. It’s weird and formal and wrong. Your first and second paragraph should provide an answer to Who are you and why are you in my inbox?
Next, turn your attention to them
In Cover Letter 1, I use paragraphs three and four to subtly demonstrate that I’ve done my homework. I talk about how I’ve been watching this company grow. I tell them about a pattern I’ve noticed in their marketing. I quickly try to highlight what I’ve seen to be true from an outsider’s perspective.
If paragraph three is all I’ve-noticed-you-and-think-you’re-cute flirtation, then paragraph four is your chance to step up to the plate and announce that you’re here to help. Notice my second sentence: ‘I’m fascinated by figuring out how to ____, and I know my experience in ____ and _____ could help you solve that problem’ I’m already hinting at ideas for where I think I could provide value, and I don’t even have the job yet.
Never forget how valuable an outside perspective is to any organisation, throughout the entire job search process. Leverage your outsider perspective whenever possible. The ‘can’t see the forest for the trees’ phenomenon is a dangerous but common poison for businesses. Experienced candidates (for senior or executive level roles) will often be asked to critique a company’s performance on something without context so that the company can discover and correct problematic assumptions that are being made internally.
The ‘PS’ section
This is an opportunity to infuse your application with one extra personalised moment in order to start building that relationship with (fingers crossed) your future co-worker. Use the space to inject a just-between-us quip that will snap the reader back to attention so that they’re inspired to go back and read from the beginning if they haven’t already.
Example: I bought the new Chelsea boots that you guys have been hyping on Instagram and am now obsessed. Should have bought two pairs.
Including a ‘PS’ section is huge strategic tool in email marketing. People read so much content on their phones all day long that they’re prone to want to skim everything. Good marketers know that, and they plan for it. Because of where the PS is located on the page, at the bottom, you will catch the people who have only been skimming — and, if nothing else, you will reaffirm that you have gone the extra mile in order to personalise.
The basic structure to follow
First, it’s about you …
Paragraph 1: Introduce yourself and what you do.
Paragraph 2: Provide more context about yourself or your skillset.
Then, it’s about them …
Paragraph 3: Talk, as specifically as possible, about why you want to join this company.
Paragraph 4: Talk, as specifically as possible, about how you plan on helping them achieve their goals.
Cover Letter 2
I hate cover letters as much as journalists hate pitches, so I’m going to give you four good reasons you should hire me in listicle format:
In all seriousness, I think I’d be a great asset to the media team. Please do get in touch so that we can chat a bit more about what you’re looking for in a candidate, and how I might be able to help.
Cheers,
Alexa
As you can clearly see, Cover Letter 2 is far too specific to me and my life to be followed line by line. Please don’t do that, it would be super weird of you.
I offer it up as a reminder that you can break any and all rules regarding what you think a job application ‘should’ look like. A reminder that magic can happen and doors can open when you break the rules in a way that strikes the right chord with the right hiring manager. Magic can happen when you find your people and signal that you, too, are one of them.
This cover letter — which is, word for word, exactly what I sent in with an application — would read as arrogant and obnoxious to the wrong audience. The reason I knew I could pull off this kind of tone had little to do with the role and much more to do with the company itself. They had a reputation for bravado. I knew that approaching them with a high-powered alpha vibe would work. Lo and behold, I sent in an application (out of the blue, without having any connections whatsoever with any employees) and got an invitation to interview within a couple of weeks.
One part comedy, one part respect
If the sassiness of Cover Letter 2 appeals to you, please note the crucial tone change in the last paragraph. I leave things on a more professional, more respectful note — poking fun at my own bravado. I’ve successfully illustrated that I can be charming and cutting edge, but at the end of the day, I know this is a business situation and not a theatre production.
In defence of the listicle format
Beloved by the internet, the listicle is basically a numbered list of paragraphs. The listicle is a way to structure an argument. This is a blade to wield carefully in a professional context. It can read as overdone or cheesy. The underlying concept of skimmability remains crucial to a successful job application, though. The recruiter on the other side of the screen is reading the same 19 Ways To Tell Your Dog You Love Her This Valentine’s Day articles that you are, meaning that their brain will be attuned to digesting content in this style.
As British journalist Steven Poole puts it:
The listicle is seductive because it promises upfront to condense any subject into a manageable number of discrete facts or at least factoids. When you embark on reading an ordinary article, you have no way of knowing how many things it will tell you. Maybe 15, maybe two. Frustrating. Plus, if you’re reading online and it’s more than a single screen long, you can’t be sure when it’s going to end. A listicle keeps helpfully informing you how much of it there is left.
While the tone I use in Cover Letter 2 might be entirely too obnoxious for either you or your potential employer, there are ways to soften the edges and leverage the bullet point style to get your point across. People like having their expectations managed. Bullet points (or listicles) give you a straightforward way to lay out your key selling points in the cleanest way possible.
A more subtle way to leverage the listicle format
A sentence to introduce yourself and what you do.
List 1: Here are three reasons why I’m the right person for the job:
List 2: Here are three things I’d be excited to tackle in this position, based on what I know so far about the company:
A sentence to say you’re excited about the role and want to speak more about it soon.
BONUS: LENGTH AND PARAGRAPH BREAKS
Whether I am using the listicle format or not, notice that I’m hitting return after every couple of sentences, sometimes even after one sentence. I’m doing this so that the entire cover letter (or cover email, in some cases!) is easier to skim and easier to read on a mobile phone.
The vast majority of email clients (like Gmail) and job application software programs are built using something called ‘responsive design’. When a website is responsive, any written content expands or contracts to fit the size of the screen: laptop, tablet, mobile phone, etc. A paragraph that looks short and sweet on your laptop will take up the whole screen on your hiring manager’s phone screen. Yes, someone might be looking at your application while commuting into the office.
Putting in a few extra paragraph breaks gives your words some breathing room. Your cover letter immediately seems more modern, friendly, and personable — no matter what size the screen is.
And that’s all there is to it. Cover letters and first dates have a lot in common. Your goal is to be flirty and interesting and intriguing enough that they will want to call you. You don’t need to explain everything in this single document, just like how you wouldn’t try to tell a date your entire life story during the first meeting.
Most importantly, don’t be so afraid of them. Cover letters are not the be-all and end-all, and certainly not for any positions that don’t require you to be a world-class writer. It’s okay to have some fun. It’s okay to speak like the modern human being that you are.
Step 4 task list