How to Tell Your Career Story in Your Job Application, with Scott Clyburn

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One way to stand out above other applicants is by telling a compelling story- your career story. But research shows that only 35% of applicants write a cover letter. Find Your Dream Job guest Scott Clyburn says you need to use that cover letter to create a “greatest hits” list of your career achievements. Distill your accomplishments down to those that had the most success. Curate your resume to show an employer how your experience will make you an asset to their company. And do enough research to allow you to speak about the company knowledgeably. 

About Our Guest:

Scott Clyburn is the founder of  North Avenue Education. His company offers test preparation, study skills coaching, and academic tutoring. 

Resources in This Episode:


Find Your Dream Job, Episode 395:

How to Tell Your Career Story in Your Job Application, with Scott Clyburn

Airdate: April 19, 2023

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 get the work you want.

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When you apply for a job, you may think all you need to do is give facts about your qualifications.

That’s a mistake, says today’s guest. Every application should tell a story.

Scott Clyburn is here to talk about how to tell your career story in a job application.

He’s the founder of North Avenue Education. His company offers test preparation, study skills coaching, and academic tutoring.

He joins us from Portland, Oregon.

Well, Scott, here’s where I want to start- why do you need to tell your career story in a job application at all? Shouldn’t your credentials and your experience matter most to an employer?

Scott Clyburn:

Yeah, that’s a great question, Mac. As a small business owner, I get a lot of resumes on my desk, and many of them come without cover letters. It’s actually quite common for job applications to come without a cover letter these days. I’ve heard only about thirty-five percent of applicants submit a cover letter when it’s optional, and really only thirty-eight percent submit it when it’s required.

So, employers, recruiters, and hiring managers are sifting through a lot of applications with just that resume. And so, that’s why I think it’s really important for your resume alone to tell a compelling story about who you are, what your qualifications are, why you’re choosing to apply to this particular role or this particular position, and why the recruiter or the hiring manager should give you an interview.

Mac Prichard:

I meet many candidates, and I expect you do, as well, when you’re interviewing applicants at your company who think, well, I’ve got these educational credentials. I had these jobs with these titles. That alone should be enough for me to get a job offer, or rather an interview. But they’re not telling their story, Scott.

Can you talk more about, what’s the difference between having a well-written resume and other application materials that lay out what you’ve done and an application that not only talks about your qualifications but tells your story and how those two things are different?

Scott Clyburn:

Absolutely. Yeah, you know, here are the questions; I want to start by framing it about what the recruiter or the hiring manager is gonna be thinking when they review your application and particularly your resume. So the questions that they’re probably asking themselves are things like this: why did this person take those jobs, those particular positions before this one, or before applying to this one?

What’s motivating this person to make a change now? Maybe it’s a career change. Maybe it’s an industry switch. But, whatever it is, employers want to know what’s motivating an applicant to desire a new position. And that’s also gonna help them make a decision about whether they think they can provide that thing that applicants are looking for in a new position.

And then, finally, recruiters and hiring managers are often asking themselves, why does this candidate think that they’ll be particularly successful in this role? And so, those are the questions that candidates can be sort of thinking about and mulling over when they curate their resume and their entire job application materials.

So a great metaphor I like to use is that your resume is really not so much like your rap sheet as it is your setlist. If you’re a musician, you have a different setlist, you know, every night, every performance, every venue, you know, every audience is different. So you have to kind of be thinking about what is going to move your audience. This particular interviewer, or this particular recruiter, at this particular company, in this particular moment in time. What are the kind of songs from your repertoire that are really going to connect and resonate with this audience? That’s gonna help you tell your story.

Mac Prichard:

So think about why this job, what you offer, and the difference that you can make. And that’s a great metaphor, the setlist, and your experience, Scott, because I know you look at a lot of applications. Do most candidates do this? Do they tell that career story? Are they offering that setlist to employers?

Scott Clyburn:

By and large, no. By and large, the interviewing team or the hiring team has to perform most of the leg work to see that throughline, to see that narrative, that compelling story, that explains why an applicant is here looking for this particular position and whether they’ll be successful once given the position. So, I think it’s really an opportunity for applicants to stand out to do this.

Another thing that they can do to really make this effective is to know what their employer cares about, what this particular employer, this company, cares about. What’s the culture like? What are the goals? What is the mission? And then speak that language. Because it’s really oftentimes the sort of small talk that happens at the beginning or the end of an interview that hiring managers remember and help a candidate stand out. It might not be so much the list of achievements or tasks executed in prior positions. It’s that common language and that common connection that you forge.

Mac Prichard:

Scott, what do you think stops candidates from telling their career story when they’re putting their application and materials together or going into an interview?

Scott Clyburn:

Yeah, I think candidates, well, first of all, there’s not a lot of information or training or coaching out there for how to build a compelling application. Some colleges and universities have departments for this, but most of the time, applicants are kind of winging it, or maybe they’re going to the internet, and they’re looking, for example resumes or examples of cover letters, or maybe they’re using a template within Google Docs or Apple Pages. And they’re just kind of filling in the core information. They know the facts of the roles that they’ve had in the past, maybe they’re even looking at the past job descriptions that they’ve held in the past or the job postings of the companies they’ve worked at in the past and they’re just kind of cut-pasting.

So, I think it is a real opportunity to stand out if you’re able to put a bit more elbow grease, so to speak, into crafting a document that’s going to be memorable, that’s going to be compelling, that’s gonna tie all of those loose ends together and explain, okay, I went from point a to point b and now I’m at point c, and it really makes sense that I would land in a position like yours, or like this one that I’m applying for.

Mac Prichard:

Well, let’s talk about how to do that, how to tell that story. I know you have a number of tips, and let’s start with resumes and I also want to talk about cover letters and interviews because that requires slightly different approaches as well. But when you’re putting together that resume, which is usually the centerpiece of your application, one of your first tips is to be selective about what you include. Why is this important, Scott?

Scott Clyburn:

Yeah, it’s important because employers don’t want to read long resumes. By and large, these recruiters and hiring managers are spending five minutes max looking through each application. And so they’re not gonna scroll upon page after page looking for the details that will really kind of help them make a judgment about inviting you to an interview.

You have to do that work. You have to be the one that’s distilling that information, paring it down, showing them the condensed, the greatest hits, you know, go back to that metaphor of kind of a setlist or a musician. What are your greatest hits? What are you most proud of? What are your achievements that you think really make you a stand-out candidate?

So part of that is focusing on your achievements, not on your roles or the specific responsibilities that you’ve executed in the past. And a good way to frame this is, as an applicant is, what are you most proud of in your prior roles? Think about what did you accomplish there? What do you kind of look back and say, yeah, I got great feedback about that one presentation? Or I really was proud that I hit those numbers in the second quarter of that year.

Make that sort of the key feature of that line item in your resume, and make sure that it ties in, especially with the new application or the new position’s goals, values, and mission. So you have to know this employer pretty well and what is the language that they’re gonna be looking for. If they say something like customer service in the job application, then you need to say customer service two or three times in your resume. It needs to stand out. It needs to be something that when they scan, they’re gonna connect with and notice.

Mac Prichard:

So think about your greatest hits, continuing the setlist metaphor, and what you’re most proud of. That’s a great tip.

We’re gonna take a break right now, Scott. So, stay with us when we come back Scott Clyburn will continue to share his advice on how to tell your career story in your job application.

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Now, let’s get back to the show.

We’re back in the Mac’s List studio. I’m talking with Scott Clyburn.

He’s the founder of North Avenue Education. His company offers test preparation, study skills coaching, and academic tutoring.

Scott joins us from Portland, Oregon.

Now, Scott, before the break, we were talking about how to tell your career story in your job applications, and one of the points you made at the end of our first segment was talk about your achievements, your greatest hits.

When you, as an employer, are reviewing applications, do you see material in those applications, cover letters, resumes, and other content that you wish applicants would’ve left out because it simply wasn’t relevant?

Scott Clyburn:

Yeah, that’s a great question. The top things that I skim over or kind of ignore in an application are non-industry experience or experience that comes from another industry and might not really be applicable. I would only include that as an applicant if you can point out how it relates or if you’re particularly proud of an accomplishment.

Also, I see, oftentimes, academic info that’s so far in the past that it seems irrelevant, like if you have one or two advanced degrees, I don’t need to know your undergrad GPA or the fact that you got dean’s list in your sophomore year.

Also, hobbies; sometimes, people include hobbies at the bottom of their resume. That doesn’t seem to be super applicable. I can always ask that in their interview if I’m curious.

And then, finally, we often see skills that are kind of too vague to really appreciate. Oftentimes, I think some of these job platforms like Indeed will kind of have you do a survey about different skills, and it will say something like, you know, communication – eight out of ten, and I just don’t really know what that means. So it’s not usually something that I put a lot of stock in. I kind of just skip over it.

Mac Prichard:

Thanks for sharing that. Another tip you have for telling your career story in your job application, and you mentioned this in the first segment, Scott, is to show how you fit the company culture.

How do you do this, Scott? Particularly if you’re not all that familiar with the company. How do you get up to speed both on their culture and show in your application materials that you would be a good fit there?

Scott Clyburn:

Yeah, culture is kind of a buzzword these days, but it is important to acknowledge and recognize and be familiar with, especially when you walk into a first interview. It could be helpful to scan the employer’s or the company’s website. Maybe, if you can, talk to someone who maybe works there or used to work there. LinkedIn is a great resource of this. And just know a little bit about kind of what the culture is like at that company, how to connect with people who work there.

It’s, as I said in the first segment, Mac, it’s often the serendipitous small talk that interviewers remember after the interview ends. It’s sort of reading between the lines of the job posting or the website copy is really gonna help candidates prepare to connect with the interviewer on that level.

Mac Prichard:

Any tips for how you’ve seen candidates take advantage of that small talk before or after an interview, particularly introverts, that show that they indeed might be a good fit for the company’s culture?

Scott Clyburn:

Yeah, that’s a great way to get into this a little bit deeper. So, I’ll share one tip that worked well and then another one that didn’t.

One time an interviewee had read pretty extensively on our blog, and our tutors and staff write our blog posts. We don’t source that out. So, there’s often some personal color in the blog posts. And so, they were able to kind of bring attention to or call back to a joke that was made in a blog post, and I could tell that they not only were familiar with our website and kind of the content that we were producing that we thought was valuable to kind of share with the world, but they got the kind of humor that passes in our workplace, and by and large, that’s really geeky, nerdy humor, by the way. But, yeah, that was a really successful way to connect with us and our team culture.

And then an unsuccessful way is just anytime an applicant doesn’t really have a sense for the population that we serve. If they come in talking about, I’m really excited to work with this kind of student or this kind of client, and I think to myself, you know, that’s not really our client. That feels like a mismatch. That feels like they didn’t do their homework, so to speak, in understanding what population we serve and why that’s really a big part of our brand.

Mac Prichard:

Another tip you have for telling your career story both in your application materials and in your contact with an employer is to show how you grew in your last job. What do you mean by this, Scott? What do you have in mind? And how have you seen people do it well?

Scott Clyburn:

Absolutely it’s a wonderful way to stand out during a hiring process to kind of talk about growth. All employers really want to see their employees grow and get better at what they’re hired for and, in many cases, expand their skill sets in order to advance within the company. That’s how businesses are successful.

So, highlighting your proven experience in meeting new challenges or attaining goals, or acquiring new skills, that could be really, really valuable. It also tells employers what motivates you. What are the kinds of challenges that you really get inspired by and that help you rise to the occasion? Because that’s gonna help them get the most out of you as an employee. It’s gonna help them assess or judge if you’re going to contribute to their mission, and that’s something that they care deeply about.

Mac Prichard:

We started out in the first segment talking about the resume, but the resume alone isn’t your only application material when you’re applying for a job, and you mentioned that many people don’t use cover letters now. Scott, how have you seen candidates successfully tell their career story using cover letters and maybe other application materials like work samples or portfolios?

Scott Clyburn:

Yeah, so as I mentioned earlier, only about thirty-five to thirty-eight percent of applicants actually do submit a cover letter these days. And so, on the one hand, if you have the time to write something really polished and compelling, it can really help you stand out because you’ll be in the minority. Also, I would say, if your application does say that they ask for or they require a cover letter, you really better be writing one, and you better not write a very hasty and short one because that’s also something that stands out and that recruiters will kind of have a poor first impression of you on the basis of.

But a cover letter is a great opportunity to tell your story more extensively and to make sure that you highlight the particular roles or the particular experiences that you think make you especially qualified for this position. So make sure that it’s succinct and concise and isn’t more than a page typed out. But it does tell the story of your career trajectory, where you’ve been, where you are right now, and where you hope to go in the future with the help of this position or this new opportunity. So that’s how a cover letter can be really, really impactful and aid an applicant.

Other ways that I’ve seen applicants stand out without a cover letter; there’s a lot of very unique resume designs nowadays, and I think that I’ve seen a lot of applicants recently use images and even work samples within the resume. It was common, even starting years ago, to include a photo, and that’s- maybe there’s some questions about some bias when including that. But I think that other things like just a well-designed resume or maybe like resumes with different sidebars that include kind of different pieces of information as you scan, and again, not longer than two pages preferably because, again, recruiters don’t have a lot of time to spend on each application.

But if you can jam-pack that first page or that first and second page with a list of accomplishments and prior roles and then maybe some colorful information about, I’ve seen some folks in the past do a philosophy. What is my kind of philosophy of work? Or what is my philosophy of productivity? Or, in my case, because we hire a lot of tutors, what is my philosophy of teaching? That can be a way to really kind of stand out and have recruiters and hiring managers say, yeah, I haven’t seen someone say it that way very many times today. I connect with that, and that’s memorable to me.

Mac Prichard:

Well, Scott, it’s been a terrific conversation. Now, tell us, what’s next for you?

Scott Clyburn:

Sure, so I’m speaking with you, Mac, today in my capacity as the chief hiring manager, so to speak, at my organization. But most of my days are spent coaching and advising prospective grad school applicants. North Avenue, my company, is focused on providing high-quality and expert guidance around preparing for entrance exams such as the GRE and GMAT and LSAT and around writing the personal statement for grad school applications. And so, we’re seeing a lot of people respond to the current economic climate by upscaling and pursuing advanced degrees. So, we’re just excited to support them in the challenges that come with graduate admissions.

Mac Prichard:

Well, that’s terrific. I know listeners can learn more about you and your company, Scott, by visiting your website; that’s, we’ll be sure to include that in the show notes and the website article about your episode, and I know you also invite listeners to connect with you on LinkedIn, and if they do so, I always encourage them to mention they heard you on Find Your Dream Job.

Now, Scott, given all of the great advice you’ve shared today, what’s the one thing you want a listener to remember about how to tell your career story in your job application?

Scott Clyburn:

Yeah, I think the one thing I want listeners to take away from this conversation is to curate their resumes like a musician’s setlist. Know your audience and strategically choose a greatest hits of the songs you think will really resonate with your audience and help you stand out.

Mac Prichard:

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