How to Write a Cover Letter That Makes You Stand Out, with Kai River

Are cover letters still relevant in a world with applicant tracking systems? Absolutely, says Find Your Dream Job guest Kai River. Your cover letter is a chance to tell an employer who you are, why you’re the best person for the job, and the experience you bring to the table. Kai says you should personalize your cover letter for each position you apply for, and share relevant stories that apply to that field or specific job. Kai also suggests keeping your cover letter to one page if possible. 

About Our Guest:

Kai River is the human resources administrator at Habitat for Humanity Portland Region. 

Resources in This Episode:

Connect with Kai on LinkedIn.

Transcript

Find Your Dream Job, Episode 483:

How to Write a Cover Letter That Makes You Stand Out, with Kai River

Airdate: January 8, 2025

Mac Prichard:

This is Find Your Dream Job, the podcast that helps you get hired, have the career you want, and make a difference in life.

I’m your host, Mac Prichard. I’m also the founder of Mac’s List. It’s a job board in the Pacific Northwest that helps you find a fulfilling career.

Every Wednesday, I talk to a different expert about the tools you need to find the work you want.

There’s only so much room on a page.

And that space can seem even smaller when you make your case that you’re the best person for the job.

Kai River is here to talk about how to write a cover letter that makes you stand out.

They are the human resources administrator at Habitat for Humanity Portland Region.

It’s part of a global nonprofit housing organization that works across the United States and 70 other countries.

They join us from Portland, Oregon.

Well, let’s get started, Kai. Why do cover letters still matter?

Kai River:

Well, cover letters still matter because it’s a way to personalize your journey that you’re going to be discussing on your resume and letting the person know what you’ll bring to that position as well because you’ll highlight yourself, highlight your experience, and then put it all together in a nice little present saying, “This is why I’m good for the job.”

Mac Prichard:

What if an employer doesn’t ask for a cover letter? Should you still write one, Kai?

Kai River:

It might be beneficial, even if they don’t request it. It will be helpful for you in the interview process as well.

Mac Prichard:

You do a lot of hiring, what do employers like you want to see in a cover letter as you’re working your way through a tall stack of applications?

Kai River:

What we like to see in cover letters is a little bit of personalization. We understand that when you’re job searching, it can be a bit daunting, just looking at lists of positions that you qualify for, and you’re like, “How do I explain that I’m actually going to be good at this job?”

Personalizing it, maybe going on our website, the company’s website, looking at their mission and vision and maybe pulling an example or two that really highlights some of those qualities within yourself or within the work that you’ve done. Also, it’s a way to get to know how you’re going to speak. It’s also kind of a culture check, seeing if you’re going to be a good fit or benefit the company more by bringing your personality and experience.

Mac Prichard:

What don’t employers want to see in cover letters?

Kai River:

A repeat of your resume. We appreciate all of the work that you put into a resume, but just seeing a list of qualifications again, or literally, the same words, copied and pasted, into a different format or document. It’s a little redundant and it tends to not pique as much interest and doesn’t highlight what we would want to see in that additional piece of material.

Mac Prichard:

Any other mistakes that you see applicants make in cover letters that you want to call out?

Kai River:

Well, when you’re personalizing, please make sure that you’re putting the right company name and address on it because one way that you can quickly personalize things is by making sure that you’ve got the correct address and location and putting that mission and vision in the first paragraph. Please make sure that you’re changing that around.

Also, the font. It should be readable. Sometimes we print them out, sometimes we don’t. Using a pretty common font, like Arial or Calibri, that are generally used in Word. It makes it easier for us to print or the programs that we use to show them on the screen.

Also, while the cover letter is something personal, please don’t put your headshot or anything like that on the cover letter because one, it can take a lot of ink, and two, we want to try and be as objective as possible, and so even some hiring places remove names to be as objective as possible. By adding that additional piece, it can just gum up the system a little bit more.

Mac Prichard:

What about generic cover letters, Kai? What do you think about someone who just sends the same cover letter to every job?

Kai River:

Well, when you’re dealing with a whole list of jobs that you’re interested in and it seems like the same job, you might be tempted to send the same cover letter to everybody, and if you just send a generic one, to us as the employer, it makes us think that you might not have done the actual digging and looked to see if we’re actually a good culture fit for you, or you might not be up as high on the potential candidate list because you’re not really highlighting something that our company might be valuing more, within the mission or vision or skill value that will come with the position.

Even if it’s just a little bit of a change, it definitely makes a big difference.

Mac Prichard:

Well, let’s talk about how to write a cover letter that makes you stand out and I know that one of the first tips that you encourage people to follow is to use a cover letter to tell your story. Why is it important to do this?

Kai River:

Well, it’s kind of like a one-sided conversation. We don’t really travel as much in elevators anymore because we are in a hybrid work environment, but it’s essentially a step up from an elevator pitch. So, you want to make sure that you’re sharing why you want to work with the employer, how awesome you are, and in the end, just explain that you would be a great asset because it’s a conversation that you’re trying to predict what they’re going to ask, based off of the job description. It can be hard to try and think about what kinds of questions they might be asking from the employer side.

Try to be proactive and think about, “Well, if I was hiring someone in this position, what would I want to know about the person that’s going to be in that position?”

Mac Prichard:

Tell us more about that structure that you just outlined. There were three parts there: say why you want to work for the employer, show how awesome you are, and explain why you’re a good fit.

What’s your best advice about how to do that and is that a structure that you should follow with every cover letter that you write?

Kai River:

Yeah, I’ll answer your second question first. I do think it’s a structure that would be good for pretty much any cover letter that you would be writing and the main reason that the structure is set up that way is, you want to, right off the bat, let the organization know, “Hey, I’m aligned with your mission and values,” and that’s going to pique their interest more because you’re making that immediate emotional connection in a way. You’re showing that you’re already aligned with what they’re already doing, and so it will help them grow more.

It’s kind of selfish, I guess, in a way, for the organization, but you’re catering to that because the second part of the cover letter, you’re going to describe how awesome you are and that really is going to be a way of saying, “I’m going to be a great fit, and here’s a great example of how I embody this. Here’s a situation where I had to work through something.” Really use that middle part of the cover letter to describe that in a little more detail than you would put in the resume.

One good way of doing this is something I learned which is called STAR. It’s Situation, Task, Action, and Response. Think of a situation where you were a STAR, or you had to work through something, what tasks you had to do to work through that, what you accomplished at the end, and the results from that. That’s a great way to highlight yourself through the whole process, and you can talk about your own thought process at the same time in that cover letter because, again, it’s that one-sided conversation.

After you’re done explaining how awesome you are, the last paragraph is a great way to just sum up, highlight one of the key parts of the mission or vision that you showed in that meaty section of the cover letter, and be like, “This is the reason that I would be a great asset to your organization.”

It kind of pulls it all together, and you want to make it so that when the person who’s at the organization who’s going to be reading the cover letter, you want to make it easy for them to already see you in the position. They don’t have to guess, “Well, why did they share that story?” Because you already created those little connections.

Mac Prichard:

Terrific.

This is great. Stay with us.

When we come back, Kai River will continue to share their advice on how to write a cover letter that makes you stand out.

We’re back in the Mac’s List studio. I’m talking with Kai River.

They are the human resources administrator at Habitat for Humanity Portland Region.

It’s part of a global nonprofit housing organization that works across the United States and 70 other countries.

They join us from Portland, Oregon.

Now, Kai, before the break, we were talking about how to write a cover letter that makes you stand out and we talked, in that first segment, about why employers want to see cover letters, what they’re looking for when reading one, and some mistakes to avoid.

You took us through a three-part structure that you can use to write a cover letter, which was very helpful. You also talked about the importance of story-telling. Could you say more, Kai, about how to apply storytelling ideas, in addition to using the STAR technique to that three-part structure?

Kai River:

With storytelling, there’s generally a beginning, middle, and end, and when you’re doing that in a cover letter, it also creates this sense of a completion of the whole story that makes it easier for the person who’s listening or reading to place in the organization.

With storytelling, definitely seeing where you started in the STAR technique, situation, task, action, and response. The ‘situation really shows where you started in that story. You can even be super honest in the cover letter, “I was not familiar with this type of technique.” Or, “I was just at entry-level, trying to learn about how things were supposed to work in this position.”

That kind of honesty really shows the growth that could come from sharing that story in the middle of the cover letter. The result at the end of the story doesn’t necessarily have to be, “Oh, I brought so many KPI numbers up,” and things like that. It could just be, “I was able to gain skills from this.”

Again, that makes the story personable and helps the interviewer see you as a person, which everybody is a storyteller in their own way, even if they don’t realize it.

Mac Prichard:

I’m glad that you made that point because sometimes I think listeners might think, “Oh, you need a special skill to tell your own story or any story.” Obviously, we’re all storytellers.

Let’s walk through some of the dos and don’ts of cover letters so that you can make yours stand out.

In the first segment, one of the don’ts that you mentioned was, don’t include a photo of yourself in your cover letter. Let’s talk about some of your “dos.” One is that you recommend looking for ways to reuse material from past cover letters.

How do you repurpose material from previous cover letters so that it doesn’t sound generic? What are some of your tips here?

Kai River:

Well, what you can do is, say you have a list of jobs that are all pretty similar and have different parts that are overlapping, so that there are certain skills they’re definitely looking for in those positions, you can reuse your story multiple times because the story in itself is a description of you, not necessarily not how it ties directly to whatever the company is looking for. That’s what the end of the cover letter is for, to show why you’re a good fit, so definitely using that middle story section, you can copy and paste it for multiple jobs and then also, in the intro paragraph, you can designate one or two sentences where you are specifically going to mention the mission and the vision of the company that you’re applying for and why you’re passionate about it, to give that introduction into the story.

That way you don’t have to be as intimidated when it comes to starting a cover letter. You’ve just got two sentences and maybe the bottom end saying, “I’m excited to work for so-and-so company,” at the end to change but it’s still personable because you know you are going to be sharing a story that directly applies to the position and that is really what is important.

Mac Prichard:

What about electronic formats, Kai? Do employers want to get a PDF, a Word document, a Google Doc? What do employers want to see?

Kai River:

That’s a very good question and it definitely changes, most of the time based on what system they’re using for tracking applications but generally a PDF of a document is the best way to share your information, via email or even put it into a computer program because most can just parse the words and put it into a text format in that, but sometimes they might ask for a Word file, or a text without the formatting, so when you have your resume and cover letter, just keep in mind that you may need to save them in different formats, so generally just the pdf and the Word file but you can save Google documents in that kind of Word file type.

Then a text version, which is literally just a copy-and-paste and put it into the word pad in Windows, that would be the basic text version.

Mac Prichard:

Almost every application is sent online now. Do you still need to include an employer’s postal address in a cover letter?

Kai River:

That’s a good point. It’s one of those older archaic types of things that have just stuck around, but it shows that you have done a little bit of work. Especially if you know that they’re a franchise location and you’re applying for a specific location, putting that specific location’s address and maybe even referring to the hiring manager by the name or position that was mentioned in the job description, you can say, instead of, “To whom it may concern,” be like, “To the director of HR or Manager of People,” at the beginning, and if you use that little bit of phrasing, it’s very formal and it kind of seems a little odd in our more technologically focused society now, but it just adds a little bit more of a personal touch.

Mac Prichard:

What about fonts? In our first segment you mentioned avoiding using small fonts and keeping the font size readable, and you suggested using common fonts, like Arial was one that you cited, but when you do that, is it okay as well to use italics, bold, or underline if you want to emphasize certain words or sentences?

Kai River:

Definitely and this applies to both the cover letter and the resume. You want to make sure that it’s easy to scan and highlight those certain parts. So, if you, say, during your story, you want to mention that you worked with a certain program, you can either bold that or you can italicize that so that when the person is reading through the cover letter, they can easily pull that part of the story out to share with their hiring team and it also shows that you know where your worth is and you want to highlight that and make sure that they definitely see that and notice that.

Mac Prichard:

Finally, what about length? Can a cover letter that makes you stand out be longer than one page? Should it never be longer than one page? What are your thoughts here?

Kai River:

When it comes to length, I would suggest no more than one page but say you’re super passionate about the position and you want to show two different stories, you can always, and this is one of the positive things about working with a PDF and sending that kind of document instead of a word file, you can mess with the margins, or change the font size just by half a point so that it’s really close to your resume font size to squeeze it all onto one page.

It’s ideal for that because we’re already going through quite a few resumes and cover letters and unfortunately it’s a time thing because there are a lot of great applicants and we want to make sure that we can give everybody a good amount of time to show what they can bring to the position.

Mac Prichard:

Well, it’s been a terrific conversation, now tell us, Kai, what’s next for you?

Kai River:

Well, for me, I will continue to work for Habitat for Humanity, Portland region, and just making sure that I’m supporting the teams that are bringing decent and affordable housing to historically left out groups in the Portland region, for home ownership, specifically, and also one thing that is great is that we have a home repair program, so I’m working with our home repair director and bulking up his team because there’s a lot of interest in that opportunity that Habitat can provide as well.

Mac Prichard:

Terrific, well, I know that listeners can learn more about you and your work at Habitat for Humanity, Portland Region by visiting the Habitat for Humanity, Portland Region website, as well as the organization’s LinkedIn page. We’ll be sure to include links for both sites in our show notes.

Now, Kai, given all of the great advice that you’ve shared with us today, what’s the one thing that you want a listener to remember about how to write a cover letter that makes you stand out?

Kai River:

You’re a star. You’re amazing and awesome, and you have something that you can bring to every position that you come to, and while it can be a daunting task to continue to apply to multiple positions, and some of them seem like the same position over and over again, what you can do is just make sure that you continue to share your story because that is what’s really important and it will definitely help you stand out amongst everybody in that applicant pool.

Mac Prichard:

Next week, our guest will be Jessica Conn.

She’s the human resources manager at Oregon AFSCME Council 75.

It’s one of the fastest-growing unions in Oregon and represents more than 33,000 workers.

When you find a job where you feel comfortable, you’re more productive and connected to your work and your colleagues.

Join us next Wednesday when Jessica Conn and I talk about why culture fit matters and how to address it in your job search.

Until next time, thanks for letting us help you find your dream job.

This show is produced by Mac’s List.

Susan Thornton-Hough schedules our guests and writes our newsletter. Lisa Kislingbury Anderson manages our social media.

Our sound engineer and editor is Matt Fiorillo. Dawn Mole creates our transcripts. And our music is by Freddy Trujillo.

This is Mac Prichard. See you next week.