The Job Search: Cover Letters

About a decade ago, I became concerned that my college students were not being intentionally trained in how to prepare cover letters and resumes so that they would be ready to apply for their first post-collegiate jobs. Because I was teaching classes many music majors took, I began to incorporate basic professional writing assignments into my classes. I was able to expand that training in my music entrepreneurship classes during the past four years, and in the last twelve months, I’ve given several workshops on cover letter and resume writing for both undergraduate and graduate students that have garnered positive feedback.

Early on, I drew upon material that I collected from how-to books, articles, and online essays, and I reflected upon what seemed to have worked in my own job searches. Since moving into administrative roles, I have gained more practical insight through the increasing number of search committees and interview teams on which I have been serving. Now, as the Director of a large music school at a state flagship university, I’ve had the opportunity to review over 300 applications for four staff and five faculty positions in the past twelve months alone; this substantial increase in my personal experience reviewing other people’s application materials has solidified my perspectives on what works and does not work in the application process. Sadly, this process also reinforced my perspective that many college graduates, including applicants who have completed advanced degrees required for faculty positions, are underprepared to navigate the job application process. That’s why I’m writing this series of blogs, so that more people—and especially those interested in working in educational settings—may be able to benefit from what I’ve learned.

Hiring collegiate faculty is highly specialized and may be only partially applicable to other types of hiring, but the staff roles that I have filled this year drew applications from people with a wide range of collegiate majors and career backgrounds, including the fine arts, but also business, medical, hospitality, and humanities backgrounds. The patterns—both positive and negative—that I have observed show up in applications from people representing diverse collegiate majors from many different schools, as well as a broad range of past work experiences.

So, the first thing I want to address is the cover letter. I am going to limit my discussion in this first blog to the broad content of cover letters; I’ll address aspects of the mechanics of cover letters in the next entry in this series.

First and foremost, as applicants, you must address the job as posted in your cover letters. This means you must avoid submitting three types of cover letters. First, do not submit a short, generic cover letter that you’ve written to accompany your resume for every job to which you will apply. Second, do not submit a somewhat longer and more detailed cover letter that is a broad introduction to yourself as a person and potential employee, filled with vague or clichéd descriptions of yourself as—for example—punctual, hard-working, and problem solving. A surprising number of people submit these kinds of letters, and they are not distinctive. As a result, those applicants do not stand out. Besides, your potential supervisor will probably think that it’s a given that members of her team will be punctual, hard-working, and problem solvers. Savvy supervisors want to know what you will bring to the position that will add to the quality of their teams. That requires you to write a cover letter that connects your past experiences and accomplishments to the probable demands of the new position, as laid out for you in the job description. Doing so shows your potential employer that you understand the nature of the job and field, and that you’re thinking through what you’ve learned about your own skills and abilities that are transferable across positions and roles. But when you write this kind of cover letter, avoid the third trap: be sure to write for the position as advertised and not for the ideal position to which you aspire.

Does this mean that you have to write a unique letter for every job application?

Yes… and no.

I suggest that you create a template letter that summarizes your training, experience, and skills, with concrete examples drawn from your work experience, organized around broad areas of work responsibility in your area, field, or profession. (For example, a faculty position is going to include teaching responsibilities of some sort, so have a paragraph ready to go about your teaching.) Then adjust this template—including the ordering of paragraphs, which specific concrete examples you use, and even word choice—to better align with the details of the job description for each individual position for which you apply. That may mean you will cut some of your template’s paragraphs for some letters or write new paragraphs to address unique features of a particular job description. Minimally, be sure you briefly address each main point of the job description, even those with which you may have little experience. The solution in that situation is to extrapolate from experiences you do have to assure your reviewer that you can take on those new responsibilities.  

Here’s why this is all so important: First, most of us underestimate the size of the applicant pool for the jobs to which we apply and overestimate our probable position in that pool. Therefore, we must use our cover letters to distinguish ourselves. We accomplish that by showing that we understand the role and have experiences that have prepared us to tackle the role’s responsibilities and challenges.

Second, because applicant pools are large, the busy people already working at the organizations or businesses to which we are applying who are reviewing dozens and dozens of applications cannot spend a significant amount of time on each one. Our cover letters and resumes may implicitly make the case that our training, skills, and experiences will transfer successfully to the position for which we’re applying, but busy people reviewing our materials do not have time to make that case in their minds for us. We must connect the dots in our professional story from past to present to future.

Remember, the ability to successfully tell your story is one of the most important parts of the hiring process, at every step of the way. How you relate your past training and experiences to the possible future reveals much about you: How do you think about new assignments and problems? How do you break down larger projects (not to mention your overall role) into discreet, manageable, actionable items and with measurable outcomes on a day-to-day, week-by-week, and month-by-month basis?

Finally, you must write in such a way as to make the biggest impact in the shortest time possible. Get to the heart of issues with concrete examples of past work-place successes. Don’t tell hiring personnel that you’re a problem solver: show them, with a brief summary of a past success. Don’t tell them you’re good at sales or moving event tickets out the door: show them, with a summary of relevant sales data. Don’t tell them you’re good with Excel, or InDesign, or Photoshop: demonstrate that with a description of how you’ve used software to complete projects, and offer to send a sample upon request. A letter that “shows” rather than “tells” will not need many adjectives or adverbs, which are the gateway to clichés. Let your nouns and verbs do the talking!

Do character and personal traits matter in this whole process? Yes, absolutely. But they tend to be more important during the interview process. For your initial introduction, through your cover letter, focus on your training, skills, and experiences, and demonstrate your readiness to transfer past training and experience to new situations or roles with increased responsibility. That will impress reviewers, make you memorable as an applicant, and bring your application to the top of the pile.

In summary: tailor your cover letter for the actual job description, and concentrate on concrete training, skills, experiences, and—most importantly—outcomes.