The 5 Why-Mes of a Cover Letter (aka What to Include in Your Cover Letter)

This article was originally published on Substack, where you can also get Job of the Day posts (always interesting, mostly remote).

In my last piece I reviewed why I love cover letters, describing why they're a wonderful tool even beyond the act of an application. While I implied the content, I didn't explicitly spell that out so let's do that here. Some people will still only ever think of cover letters as a chore but perhaps with additional details more of you can be further persuaded. I even came up with a fancy name for the content so you know I'm serious about it (and so I can later do a TED Talk on the topic). So coming up, the 5 Why-Mes of a cover letter.

As a recap, I love cover letters because they're an opportunity to:

• Introduce yourself
• Provide context
• Disarm your weaknesses
• Organize your thoughts
• Practice

But exactly how do you do those things, especially if you don't imagine yourself a great writer or hate writing about yourself? For all of the fretting people do about cover letters, I think there's a relatively simple format that can be applied to get you most of the way there and *still* leads to a more interesting and fruitful exercise for both reader and writer. You don’t even have to be clever or develop a silver tongue, you just need to be honest and answer some questions.

I'm not going to spend time here on the introduction or conclusion. Say hello, express your excitement to begin and close by summarizing what you said and thanking them for their time. Stories are great ways to get things going and saying you'd love to learn more is a great way to open the door to further conversation without the "pressure" of the only positive result being a job.

Why are you writing a cover letter?

Let's start at the most basic question. Love them or not, why would you write a cover letter in the first place? You're generally trying to introduce yourself to some unknown recruiter or hiring manager, to convince someone to move you to the "Proceed" pile rather than "Reject." You're trying to pique someone's interest beyond what your resume might do (regardless of how impressive it might be). We choose the information to include in a cover letter accordingly.

Here’s the overall idea:

"Hi, I'm me and I have reasons and experience for why working for this company, in this role, and/or in this industry is the right move for me and could be mutually beneficial for you/your department/your company as well. Learning more about me and my experience is a better option than dismissing me."

The 5 Why-Mes of a Cover Letter*:

Given that overall idea of what you’re trying to convey, now is when you make that overall message your own, describing those reasons why there’s compatibility and helping someone understand just why you shouldn’t be dismissed. I've come up with five questions that should be considered when writing a cover letter. The answers don't need to be exhaustive and going through them doesn't have to take up too much time, but you do need to provide yourself a few moments of honesty. Overall, you're answering different versions of the question, "Why me?," hence the fancy name.

This list has strong similarity to questions that might come up in a screen or an interview and that's a feature, not a bug. The earlier you start even informally answering those questions, the easier it will be when it happens on a call or in person. This is preparation for the entire process, not just the cover letter.

The 5 Why-Mes:

• Why are you interested in this (kind of) role?
• Why are you a good candidate?
• Why aren't you a good candidate?
• Why might you be rejected?
• Why should they talk to you anyway (given the prior answer)?

Here’s a little about each question, along with potential answers.

Why are you interested in this (kind of) role?

You've got reasons why you're applying to a particular role. There are effectively infinite roles out there and you should have a clear idea for why this one is of interest beyond "I need a job." Maybe it's the brand, the culture, the product, the industry, the specific personnel. Likely it's a combination of all of those things. And that you need a job.

Potential Answers:

• For the kinds of problems I’m interested in tackling, this role/company presents a unique opportunity.
• I have a specific relationship to this team, project, product, or company.
• Simply, I would be good at this.

Why are you a good candidate?

Your resume is (hopefully) full of the reasons why you're a good candidate for a particular role. I don't advocate for total redundancy, but you should consider your strengths, experience, and just how ready you are for the role. Some of that is what you should include, but all of it should serve as a confidence boost for just how right you are for the step you're trying to make. You're great, smart, talented, and ready for this role, they just don't know that yet. By writing this cover letter you're helping them catch up.

Potential Answers:

• My prior experience aligns closely with what the role requires.
• I’m enthusiastic to join as both a learner and teacher.
• I have specific accomplishments that demonstrate just how qualified I am.

Why aren't you a good candidate?

This and the following question might be the trickiest to answer. The point isn't to inject pessimism into the exercise, but instead to be self-aware. Given your resume, what are the "facts on the ground" that might weaken your case? Whether it's a lack of overall experience, expertise with a particular tool, or a new industry, the reason you need to consider this question is so you can potentially speak to those shortcomings either here or later in the process. You need to anticipate the questions your application might bring up and be able to address them, nipping FUD (Fear, Uncertainty, and Doubt) in the bud before it has a chance to grow. Considering why the recruiter might say no is part of the process of getting them to say yes.

Potential Answers:

• I don’t quite meet the years of experience or specific experience with a tool.
• I’ve never had this role before.
• I’ve never worked in this industry.
• Not sure my values align with this role.

Why might you be rejected?

Looking ahead to a possible outcome, this is where you spend some time anticipating what’s going to be the reason future-you says you were rejected. It may be as simple as you not being a good candidate (see prior question), but let’s add insecurities into the mix as well.

I have yet to ask any client why they haven't gotten traction and have them say "I don't know." Even if that's what was stated first, they followed up immediately with what's lacking on their resume, their experience gaps, question(s) that tripped them up, how nervous they were on a call, how they bombed a tech assessment, what person was further along in the process, ageism, etc., etc..

Some of those reasons that come up are more actionable than others. You can practice and take mock tests to help settle your nerves but you may never know if discrimination is at play. Given the uncertainty, the point of this question is two-fold. First, know the areas where you need further preparation. Second, it’s time to start considering your counter-arguments or clarifications.

With things like industry transitions, returning to the workforce, or gaps on a resume, candidates often try to hide, relabel, or ignore that those things are at play, sometimes to their own detriment. I’m going to ask you to assume the recruiter or hiring manager is smart enough to see through misdirection or omission and list of what you think your red and yellow flags are.

Potential Answers:

• I have gaps on my resumes and they may think I’m unreliable uncommitted.
• There’s domain-specific knowledge they might assume I can’t learn.
• I’m overqualified and they might think I’ll be bored or otherwise unengaged.
• I’m not an obvious “culture fit” and they might think I wouldn’t be compatiblel

Why should they talk to you anyway (given the prior answer)?

Hopefully you can see what’s happened with this line of questioning so far. You’ve effectively made a mental list of Pros and Cons for yourself as it relates this application. This question is about balancing those two sets of ideas. Some of your answers might be more hopeful or aspirational than others, but they’ll suggest the tone your cover letter should take.

Potential Answers:

• I’ve been successful at past roles and I’m looking to grow. I’m not looking to slow down now and can share exactly how great I am.
• I may not have industry-specific experience but I can absolutely share how the things I know are transferable.
• I haven’t done this role before because I just got my MBA. I’m excited to put my past experience and new learnings together to take the next steps in my career.
• My time away from the industry has left me hungry to get back in the mix with fresh eyes and a clear mind.
• I’ve been at a lot of different companies for a variety of reasons, leaving me wanting to settle in with a company, and very specific needs that this company/role can fill. I want a “home” despite what my resume suggests.
• I actually don’t know that I’m the *strongest* candidate, but I want it more than anyone else. I just need someone to give me a shot. I’m not a typical candidate and that’s the whole point.

Consider how many of these questions aren't addressed by your resume, which doesn't include motivations, relationships, or overall context. It can't connect the dots between companies, titles, and projects or address how your actual experience meets the requirements of a job description despite different industry jargon. Lastly, your resume can't speak to how you are as a colleague, what values you bring to the table, or what your short-, mid- or long-term goals are.

Putting it all Together

You have endless possibilities for how you approach the final cover letter, using the prior questions to provide the "ingredients" for how you do so. Sometimes you can lean almost entirely on your strengths while in other cases you might have things to address, or personal connections to explore. Tasking yourself with writing the world’s best, most convincing, and most original cover letter could leave anyone paralyzed at the keyboard.

The point of the 5 Why-Mes is to remove some of the pressure from the exercise of writing a cover letter by supplying you with a “grab bag” of ideas you can use. The 5 Why-Mes remind yourself of your strengths, keep you self-aware, and prepare to answer the hard questions that might come up during the hiring process. Oh, and because these answers are your own, they can help you put more of yourself on the page as well. That's the hope anyway.

If you find the 5 Why-Mes framework helpful, please reach out. I’d love to hear how they were a resource and look forward to reading your updates.

As you can tell, I’ve thought perhaps way too much about cover letters and it’s only natural that they don’t capture your attention the same way. If you’d like help understanding your career or how to put it in a cover letter, please reach out. I’m here to help.

Footnote

* Credit where due, The 5 Why-Mes are akin to an inversion of a technique from design thinking called 5 Whys. That exercise is used to determine the cause of a problem, by repeatedly asking "why" to drill closer to the root, like a precocious and maybe a touch annoying toddler. In that case it's multiple questions to arrive at one actionable solution. In this case it's multiple questions that point to various aspects of how to meet the singular goal of a convincing cover letter, a "bucket" of ideas that can be included.