A Guide to Killer Cover Letters

VOLUME THREE in the 2020-2021 RECRUITING GUIDE

Jun 19, 2020

Hello Friends!

And thank you so, so much for tuning into the third installment of my newsletter. I’m really exciting to create this kind of content for you, and I am passionate about providing resources and opportunities for students who face an uphill battle when it comes to applying to jobs, internships, and even college. In the coming weeks, I will also be posting content on college lifestyle and advice, as well as provide commentary on current events, politics, markets, and more.

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On that note, in today’s newsletter, I will be covering cover letters and how to develop rockstar CV’s that will help you stand out in jobs and internships that - unfortunately - are only becoming more and more competitive.

So, with that said, let’s dive right into it!

This newsletter (and future ones, knowing my writing style) can get very, very long, so thank you so much for your patience and time. I have divided my Cover Letter Guide into six distinct sections, so feel free to read section by section at your own pleasure.

Please note that today’s newsletter will focus more on content than layout and design: I will include resources that can help you format your cover letter to appear more aesthetically pleasing, but right now I will focus more on how - from a content-driven perspective - you and your letter can best stand out. If you are interested in learning about a human-centered driven approach to cover letter design and style, however, please let me know in the comment section below! I would be more than happy to cover this topic in future newsletters and videos, and bring in expert guests.

Also: please feel free to skip and choose sections based on your individual experience and preference. Some may be working on their tenth iteration of their cover letters; others may have never written one, or even heard of the term.

So, no matter your familiarity with the concepts, read and interact with my content at whatever speed you are more comfortable with 😊😊😊😊

What is a ‘cover letter’
Getting started
Building blocks of a strong cover letter
A quick cover letter checklist
A quick cover letter ‘anti-checklist’
Concluding thoughts

What is a ‘cover letter’

Like previously mentioned in my Resume Guide [LINK], employers will spend anywhere from 10 seconds to 1 minute scanning your application profile to see if you’re a cultural + professional fit. This includes your resume as well as your cover letter.

Authentic networking helps push your application to the top of the stack, and honestly - even then - resumes are far more examined in-depth than cover letters are. Some firms, like McKinsey’s San Francisco office, admit not even looking at them (source: friends, recruiter, and on-campus information sessions). So why bother?

Many firms still require cover letters, and they are typically used to gauge your ability to effectively write, communicate, and express yourself and your story.

If the resume is your friend hyping you up in front of others, the cover letter is you telling those stories from your own lips. But remember: you have very limited time to do so. Recruiters will spend very little time on your cover letter, unless you have been personally referred or you are applying to a targeted recruiting process.

For instance, in “target” schools like UC Berkeley (“Public Ivies”) or Stanford (pay-to-play clubs, I mean elite private schools and the “Ivies”) firms will typically have a dedicated recruiting team assigned to each individual campus. There are a limited number of spots (a soft quota, few firms impose a hard maximum or minimum) available per school, and there are typically anywhere from 200 to 400 applicants vying for 5-10 spots. The recruiting team is focused on a particular school, which means it is feasible for them to actually examine your cover letters and resumes in-depth.

That being said, if a cover letter is required (which more often than not is the case, even though it’s also the case that, more often than not, they’re not even read by the recruiters who made it a requirement in the first place): WRITE IT.

So, how do we get started?

Getting started

In a nutshell, cover letters get noticed because they tell a story.

They are very different from a resume in that resumes emphasize relevant goals and achievements, focus on critical skills relevant to the job, and are concise, well-organized, and easy to read.

Cover letters should also be concise, well-organized, and easy to read, and they should also emphasize your achievements and skills.

Whereas a resume is achievement-focused, however, your cover letter should link your experiences, projects, and accomplishments into one cohesive story: your story.

Of course, that’s much easier said than done. And by the time you finish reading this guide, you hopefully will have an understanding - and some robust tools and frameworks - that will help you think about structuring your cover letter and story.

And again, without getting too in-depth on the design principles that underlie cover letter building and development, I will say this: if you’re applying to consulting, investment banking, accounting, finance, sales, or any other ‘analytical’ business role, nobody will care if your cover letter employs fantastical designs that catch the eye.

The same can be said for roles in SWE (software engineering), PM (product management), or other technical disciplines (with the exception of UI/UX, Product Design, etc.). Indeed, in technical roles cover letters are typically not even required (ah yes, the classic STEM student dilemma: forgetting how to properly write).

While more creative roles - the arts, digital media, graphic design, architecture, etc. - would absolutely benefit from advanced design techniques, cover letters generally need to follow the guidelines outlined in today’s newsletter.

PARAGRAPHS 1-2: A Memorable Introduction

This is up to the individual, but generally you want to introduce your narrative (paragraph 1) and express your interest and why (paragraph 2).

For the former, you may briefly share your major/degree and how you found the job position and role. You may also choose to get creative and “hook” the reader. I leave this particular detail up to you, as everybody is different and tells his or story differently, not only in content but also in tone and energy. In this paragraph, I would also mention referrals and the people you know within the company/role.

In the latter, expressing your interest can be broken down in a number of ways. You can talk about the firm’s initiatives and/or projects, and why they excite you. You can talk about its people (in my opinion, this is the best approach — I’d begin by mentioning your referral - if relevant - and your relationship and what you’ve learned from coffee chats and mentors).

No matter what route you take, I suggest you focus on people, not products or profits. Focus on the personal, on the stories and insights you’ve learned from others in the firm and why that has lead you to this point. If you write down company talking points you can find with a simple Google search, you won’t be doing yourself any favors.

PARAGRAPH 3: Examples of Relevant Experience + Accomplishments

Your first two paragraphs focus on “why them.” Now, it’s time to answer “why you.”

This paragraph will be more dense than any other paragraph, but the reason why I suggest you use only one paragraph is simple: you can’t tell all your stories in this one cover letter. You will have to pick and choose the most relevant and impactful ones - or one, for that matter - and distill it to one paragraph in your cover letter.

Your interviews will allow you to flesh out this experience - and other ones - in greater depth. For now, I suggest listing out all your projects, work experience, skills, etc. on a blank document (which we already did upon reading my Resume Guide, so if you’ve done that you’ve already got a head start!) and begin examining each and every single one of them for their relevance to the job you are applying to.

Match your experience and accomplishment with the position. Prioritize impact - don’t provide a laundry list of accomplishments (that’s what your resume is for!).

And in case you haven’t been catching the hint: yes, just like with the resume, this means you have to write a unique cover letter - with a different story and/or experience - for every single job and position you apply to.

PARAGRAPHS 4-5: Conclusion with a Call-To-Action

Your fourth paragraph (which could be your final paragraph, if you want to merge your conclusion with your call-to-action) should be about re-emphasizing your passion and interest for the position and company and why you would best fit in the role.

In your final paragraph - whether it is its own distinct paragraph of it’s merged with the paragraph above - be sure to also thank the reader(s) for his or her time and consideration. Make it clear this is a position you are interested in; anybody can send in a copy-paste template cover letter, but few can make the ending more personal. Address it to the reader him or herself. Add your own unique flair. And always suggest that you are excited to offer more information and that you’re looking forward to talking with them. Include your email, phone number, and contact information.

You may notice each paragraph, with its own self-contained story, connects with another to form a larger story that is felt and shown, rather than told.

Your first paragraph is who: who are you?

Your second paragraph is why: why are you here?

Your third paragraph is, again, why: why you?

And then your fourth and fifth paragraphs focus on how and where: how and where can you best be contacted and reached for next steps?

Now that we know how we can best structure our thoughts and letter, it’s time to focus on the building blocks. How exactly do we tell our story, and how should we go about conceptualizing the very content of our cover letter?

Building blocks of a strong cover letter

We have the structure, the blueprint, to our cover letter plans. The next step, then, is to determine what the building blocks and components for our letter are.

For starters, here are some questions you should ask yourself before writing the letter:

How your work experience meets job requirements
How your skills meet the job’s requirements
Why you want to work at the firm/organization

You may notice there’s a theme emerging.

You shouldn’t try to fit your whole life - all your professional and academic experiences, accomplishments, and achievements - in the space of a single cover letter.

It’s tempting, but ultimately counter-productive.

Remember, your cover letter will only be read in a 10 second to 1 minute window.

Your cover letter ultimately is a curated selection of stories that gives the recruiter a clear idea of who you are and how you can add value to the company and team.

Your letter therefore needs to provide this information and leave the recruiter convinced that you are the right person for the job, and to accomplish this you should be using the requirements of the job to guide the content of your cover letter.

STEP ONE: Do Your Research

Research the job description: understand what are they looking for, what’s the day-to-day look like, and what would be your major tasks, goals, and responsibilities.

Go one step further and research the company and position. Chat with your network and understand, from their perspective, what the job is actually like. What are some up-and-coming projects and initiatives? What are some things applicants don’t know but seasoned veterans do? By conveying this level of detail and insight, you will impress recruiters. They will know you wrote them a custom cover letter, and that you really did your homework. Not many do, and that will make you STAND out.

STEP TWO: Hone-In on Your Story

Once you have identified what the job/recruiter is looking for (re: job description, coffee chats, etc.), pinpoint one story (re: project, experience, accomplishment) you will then use as the crux of your third paragraph.

Hypothetically, let’s say you’re applying for a product management internship (APM) for Twitter. After conducting your due diligence, you observe the following bullet points on what Twitter says it looks for when recruiting new full-time APM’s.

Rising fourth-year undergraduate students (preferably a technical major)
Desire to develop a career in product management with a strong focus on developing social consumer, developer, and marketing products at scale
Demonstrated experience working with and knowledge of consumer behaviors
Strong quantitative background to support data-informed decision making
Ability to plan and drive execution to grow a product from concept to success
Strong interpersonal skills and ability to work well in a cross-functional team environment
Exceptional communication and presentation skills
Passion for media and social platforms preferred

Among other things, the job description mentions a preference for technical majors, prior experience in PM, product, or related fields, and strong communication skills. You can pick out these three areas as the core focus of your story, or you can pick completely different areas. I would suggest 3-5; any less won’t be compelling, and any more might be too overwhelming.

Here’s an example of how I would tackle this task. I would think about my previous roles, and choose one that emphasizes my strengths in communication and presentation, leadership and cross-functional teamwork, quantitative skills to inform data-driven decision making, ability to plan and drive execution to grow a product from a concept to success, and demonstrated interest and passion for media platforms.

For instance, in my previous role as as marketing manager for my school newspaper, I lead a team of 10 associates in prototyping and building our first-ever mobile app. We worked with Design and Software Engineering to design our initial UI, and we tested our UX by running user research studies and interviews with randomly selected students and community members. By collecting user research and analyzing results, we were able to rapidly iterate our app from concept to prototype to finished product. As we were building our product, I was meeting with board members, editors, managers, and our Editor-In-Chief to manage internal stakeholders and communicate our progress, and was able to build cross-functional support and expertise for product conceptualization, development, management, and launch.

This isn’t exactly what you would write in a cover letter, but it’s a good start for thinking about your experiences and how you can relate it to the job position in a way that is relevant, impressive, and illustrative of your present impact and future potential.

STEP THREE: Adapt Your Tone

Ever heard the advice “Be Yourself?”

Yeah, it be like that.

You do have to be yourself in your cover letters, but what does that mean?

First, rely on structures and frameworks, but not on vocabulary and language. Don’t use buzzwords and business/technical lingo for the sake of using business/technical lingo. Trust me, no matter how bad you think your writing is, anything is better than the same copy-paste cover letter repeating empty platitudes like “Self-Starter,” “Detail-Oriented,” and “Forward-Thinker.”

Second, be yourself but also, like, be the you the companies want to see. I would love to be proven wrong, but let’s face it: companies aren’t looking for you. They’re looking for the right person at the right time and place for the right job. Moreover, the you they’re looking for is relative in the sense that, even within similar jobs, different companies and environments are looking for different things. For instance, what a 200 year old law firm is looking for is likely highly different from what a two-week old startup busy hemorrhaging its $two million in seed money from Y-Combinator is looking for. Accordingly, your tone will be different, and how you express yourself - not just what you choose to express on paper - will be unique depending on who your audience is.

For instance, if the firm has a more playful culture, imbue that playfulness and irreverence in your cover letter. You can play around with your design and use more vibrant colors and fonts, and your language can be more casual by employing everyday vernacular (re: slang, casual terminology, etc.). If you are applying to a more serious firm, however, then you will want to have a more vanilla approach.

In general, take creative risks only when you are certain the firm is tolerant, perhaps even appreciative, of that kind of tone.

STEP FOUR: Begin Writing

Now that you’ve nailed your story (content) and tone (style), you are ready to begin writing your first draft.

Once you’re done writing your first draft (or now, if you’ve already written your cover letter, and you’re dying to learn more about cover letters), hop on to the next section to see what you’re doing right… and what you may ‘unintentionally’ be doing wrong.

A quick cover letter check-list

As you examine your cover letter, keep these best practices in mind:

Write an original letter. Just like with your resume - and as previously mentioned in this guide - tailor your letter to fit the job and role you are applying to. It’s tough writing 20 variations of what ostensibly could be the same copy-paste letter, but trust me: future you will be SO thankful of present you for doing this.
Write to an actual person. Find the name of the recruiter, manager, and/or executive reading your cover letter. Ask who you should address the letter to during information sessions, career fairs, and coffee chats. Some companies also have recruiters’ contact information on their websites. For instance, BCG has a college-specific recruiting page that outlines who handles recruiting on a campus-by-campus basis. On the safe side, you can address your letter to the senior-most person. That being said, I believe conducting your due diligence via coffee chats, career fairs, and information sessions is your most effective route.
Align your letter with the job description and company culture + mission.
Be succinct and concise. Your cover letter should not be more than one page and 5 paragraphs. In fact, the shorter the better. Cover letters benefit from the “less is more” principle; if anything, it should tease the recruiters and provide a compelling build-up, and during your interviews you can fully expand upon your experiences and blow them away with detail (but more on that in my INTERVIEW GUIDE, which will be coming in ~ 2 weeks 😊).
Proofread. Don’t just double check. Triple check. Get a friend, colleague, and/or mentor to review it too. Their eyes won’t be as tired (re: lazy) as yours scanning your cover letter for the second, third, even tenth time. Have them critique it. Even better - have someone inside the firm critique your cover letter and give you pointers on what the firm itself wants to hear and see in application profiles.
Convert to PDF. Just like with your resume, PDF versions are cleaner and more universally accessible. Word Document often alters formatting, especially if you’re playing around with more creative elements. I typically use Pages to format and design my cover letters, but I began with Word and Google Docs.
Follow up. Your last words should always be to offer following up on the offer and discuss next steps, as well as convey your excitement for applying to the job. This demonstrates interest and passion for the role, and by providing your contact information it shows you are serious about the job/internship and want to learn more / prove yourself.

A quick cover letter ‘anti-checklist’

On the flip-side, there are certainly worst practices recruiters see time and time again in the thousands of cover letters they see on a day-to-day basis.

Here is what NOT to do when preparing your cover letter:

Sending the same letter. I can not tell you how many people send the same letter again and again, and being rejected time and time again, wondering why they aren’t seeing different results [I believe that’s what they call the definition of insanity]. I understand you must be incredibly busy with school, clubs, part-time work, worrying about financial aid and paying rent, let alone recruiting and stressing about jobs and internships. This is so, so tough, and it breaks my heart when people lose their initial passion for recruiting when they see just how hard it can be. But don’t lose hope. You will find that writing tailored cover letters and resumes is actually easier than you might expect. Begin by simply listing all your accomplishments and stories in bullet point fashion. Keep them in a master list, or a master resume, if you will, with all your bullet points and stories intact. This will make it easier to pick and choose which ones you will express in tailored resumes and cover letters in the future. I can comfortably say that, by doing this, you will spend no more than 20 minutes formatting and tailoring your resume and cover letter for any given role.
Being long-winded. Please don’t go over one page. Admittedly, this is my greatest weakness; if you couldn’t tell from these newsletters, I just have TOO MUCH to say, write, and express. If you find yourself going over one page, ask others to critique your work. We get overly attached to some ideas, but they can be more objective and help us “cut the fluff” and pinpoint what actually matters.
Forgetting to proof-read. You already worked so hard making the letter; reading it one final time before you send it is the least you can do for future you.
Going off on tangents. The company has given you a description of the job and its roles, responsibilities, and requirements. You’ve been given a script, and yes: you can ad-lib. But ad-lib too much, and suddenly your cover letter is talking about your time volunteering in Nicaragua and sustainably farming mangoes when the job is about building financial models and engineering multi-billion dollar cross-border M&A transactions. Stay focused.
Failing to hit the right notes. Again, you’ve been handed a script. You don’t have to follow it word-for-word, but think of it as a music sheet. You have all these notes you can play, and you have the liberty of improvising and building upon what you’ve been given. But again: don’t stray too far. Focus on what matters. Focus on the job description, and align your past and present experience with future obligations and expectations. Show that you are a professional, technical, and cultural fit, and demonstrate what you can contribute to the team + firm.

Good luck, and as always: when in doubt, always ask for help! Have others review your work, and seek both personal sources - friends, family, mentors - as well as institutional ones (your career center and its career counselors). If your school does not have a career center and/or career counselors - or if they do but you just can’t be bothered spending a month on the waitlist getting an appointment - feel free to reach out to me and I would be more than happy to quickly review it 😊😊😊😊

Concluding Thoughts

Cover letters are important, but don’t put all your eggs in one basket. Networking is still, by and by far, your most important recruiting asset.

A strong relationship is enough to turn heads and pass your cover letter and application profile to the top of the recruiting stack. If you ever wonder why there are some students who get the internship/job despite their relative lack of experience, know that networking can make all the difference.

While this, in many ways, may be problematic (re: nepotism), the fact of the matter is recruiters and managers simply don’t have the time, energy, or resources to fully examine every single resume that comes their way.

Your mission, therefore, is to get them to look at your cover letter. And this can be accomplished via authentic networking.

Next, your objective is to impress. And hopefully, today’s guide has shown you how to do just that.

Thank you so much, and stay tuned for my next newsletter where I will go over my tips and tricks for acing your INTERVIEWS!

Babble by Bryan