Andrew Trappen on how to write cover letters

In today's episode, Cover Letters, they're back! Andrew Trappen shares with us the value of investing in cover letters as part of your job search toolkit.

Provide the employer with a glimpse into the why behind your application.

Cover Letters Are Worth Your Time

by Andrew Trappen

During my previous years recruiting, I rarely read cover letters and I rarely had hiring managers who asked for cover letters.  It was later when I was actively looking for work that I gained perspective on their importance.  It happened when I applied to a company in the travel industry where a friend there told me that to be considered seriously, they need to know you are passionate about travel.  Given I had never worked in the travel industry before, it became clear the cover letter was my opportunity to explain what travel meant to me.  That was one employer that clearly values the information you provide in a cover letter. 

The fact is you usually don’t know which companies, which recruiters or which hiring managers value the cover letter.  The goal of this podcast is that you stop gambling on the cover letter not being important any longer.  You would never allow an attorney to represent you in a case knowing they would leave out some of the evidence proving your innocence, would you?  Then why would you leave out evidence proving your qualification when you apply to jobs?

So why would we so often skip providing a cover letter?  Usually, I hear candidates say they don’t have time.  I believe that reason is symptomatic of the real problem: not being prepared.  Not being prepared to submit a cover letter makes doing so difficult and time consuming. 

The Value of Cover Letters

1. The primary value of cover letters is to provide the employer with a glimpse into your purpose, mission, passion; your why.

  • Resumes share your career history, the physics of your professional path, the work you've done and the value you've created, as well as your education, certifications etc.  It’s all about WHAT you did, WHEN you did, WHERE you did, HOW you did it…. 
    • Resumes need to be accurate and relevant to the job.
  • The cover letter expresses the WHY behind your expression of interest: what about your values, your mission, your passion, on top of your experience make your right for this job, this company.  The cover letter tells readers your application is meaningful, not just another applicant looking for whatever job they can get.
    • Covers letters need to be authentic and meaningful to the employer.

2. Secondly, the employer has the chance to understand how well you write.  Your cover letter will include 2-3 paragraphs that indicate how well you write, which is more important of course if the position includes significant written communication.  Either way, the cover letter either impresses the reader, or not.

  • We're going to make each sentence important and apply our best word selection to build the most concise powerful sentences possible.
  • For help improving your writing, see "The Elements of Style" by Strunk & White

3.  Last, but not least, another value gained from creating a cover letter for each application is validating our depth of interest in the job we’re applying to.

  • Simply put, if you have trouble making the time to submit an effective cover letter, you should not waste the time applying. 
  • Likewise, if you build a meaningful a well written cover letter, you can leverage the language and messaging from that letter when you are interviewed.

Preparing to Create Powerful Cover Letters

If you are convinced cover letters are important, learning how to effectively prepare and create them will help you make them an effective tool in your search.
1. The first step to prepare to create the most valuable, that is the most authentic and impactful cover letter possible, is to understand and have language for our own strengths, preferences, path and more; to know ourselves.

There are several resources we can leverage on our path toward deeper self-understanding:

  • Personality Type Assessments – Myers Briggs (MBTI or 16personalities), DISC, and others.  You can find some free and low cost versions of these assessments online. 
    • With these, you will affirm your preferences, and you may get some language surrounding your strengths or style that could related to WHY you are interested in job or employer.
  • Personal development books/Programs
    • First, from one of my favorite author’s, Debra Trappen, “Fire UP, Taking your Life and Business to 11" in which you go through her Core Four where you identify your values, your purpose, your niche and your messaging.  It’s not about job search specifically… but it’s about understanding ourselves.
    • Otherwise, there are many different approaches and perspectives on identifying your why.  Try Googling “Find my why”.
  • And finally get down and dirty with yourself
    • Write down what aspects of your past jobs you loved; the parts that fueled you and where you excelled.  Then write down what aspects of past jobs drained you, you loathed performing and likely did not do as well.  Make sure to write down why you felt as you did about each aspect of your work and then extrapolate your preferences.
    • Try open honest dialogue with your family, friends, and trusted colleagues.  Open a conversation about each other's why, purpose… without hearing more from you, what do they currently think your purpose or “why” is?  This type of vulnerable conversation is best in trusted relationships - but it can be quite fun and it will likely deepen connections.

There are also career coaches out there that will walk you through their version of looking within.  If you know you will need the accountability partner, look them up or follow TheCareerCue for guests who are career coaches you can connect with. 

2. The second part of preparing is to understand the opportunity and the company you are applying to.  You do this for each job you apply to:

  • Read the job description carefully noting where you strongly meet requirements and align to the job, and where you don't.
  • Reviewing the Company's CAREER and ABOUT this COMPANY section… understanding their mission, values, leadership principles… Whatever it is they deem important enough to publish is important enough for you to understand if you are applying.
  • Take a quick look at 3rd party sources like for feedback.  Do you see consistent favorable feedback that aligns to your values, purpose, preferences, etc.?
    • Don’t be too concerned with one-off bad feedback.  If you do find trending bad feedback, you may want to address that tactfully IF you get to interview, but only if responses would inform your decision if offered the job - if not, ignore it.

Creating Your Cover Letter

Now it’s time to put together what you know about yourself and what you’ve learned about the job/employer, drawing connections between your preferences, passions and mission to the company values, job focus, etc.  Such as:

  • Why this job is meaningful to you and your career goals, mission or purpose?
  • Why your connection to the job/company mission etc. is valuable to the employer?
  • Why your career path or combination of X and Y skills particularly prepares you to create value?

Use a business letter format if uploading/attaching your cover letter.  If you are pasting or writing into a text field, I suggest omitting the business address, and begin with the salutation.  By the way, salutations are best when you know the name of the recruiter or hiring manager, but you can also address the salutation to “The Hiring Team” or other general statement.  Microsoft Word offers many cover letter templates you can use to get started.

The main sections of the cover letter:

  • The introduction highlights what you will explain in more detail in the body.
    • 2-3 sentences
  • The body will explain the value of your candidacy in 2 ways: your motivation connection and your career connection.
    • 2-3 short paragraphs of 3-5 sentences - be concise, and very selective of the words you use.
  • The closing paragraph invites the reader to contact you, and asks for the interview.
    • 2-3 sentences with at least one contact method listed.

Begin by writing the body of the cover letter.  The approach that I use has two paragraphs:

  • First is my personal expression of my motivation for the job/company.
    • This is about how my a few of my WHY, my values or my preferences align to the job, and or the company.  This is an expression of your passion's alignment to the role.
  • Second is highlighting the connection of career path with job.
    • Not in detail, mostly at a higher level as in why your unique career path brings makes you ready for this job, or how you've worked up to this job intentionally… etc. 

Once you have 2-4 sentences you are confident about for each paragraph - Now build your 1 -2 sentence introduction…. This is stylistic and should be in your voice…. But I tend to clearly state that, I am interested in this role, because it aligns to my (Paragraph 1 - passion, purpose, preferences) and I am certain I will provide value given the (paragraph 2- strength of my AB skills,).
Finally build your closing statement clearly asking for the interview and inviting them to contact you providing a phone number or email.

Creating impactful cover letters requires the healthy investment in yourself, which will pay off in many other ways as well. Remember, do this work understanding your cover letter may not be read, but make it great so if they do read it they will be impressed and you will stand apart from the other qualified candidates.  Your first try will take longer, and over time it will become natural and one day your cover letter may end up making the difference that changes your career and life. 

Some additional Q&A with Andrew

If I'm applying for roles with similar responsibilities, can I use the same cover letter for every submission or should I customize each one based on the opportunity?

Always customize your cover letter to the degree needed to make it authentic and meaningful. 
As a point of reference on customizing, your listeners may know already that even their resume should be refined per application detailing more of this or less of that aspect of experience based on the requirements of the job. Again, always authentic and accurate.  So similarly, the cover letter needs to be authentic and MEANINGFUL for that job that employer.

How do I address a specific requirement for the role in my cover letter if I only have personal or unofficial experience in that topic (eg., budget management, event management, etc)?

Well make sure - as much as possible, to increase your chances of being selected that you apply to jobs where your resume can accurately reflect that you meet the BASIC requirements for the job.

But if you are missing a basic requirement, or perhaps a strongly preferred requirement,
The key is STAY POSITIVE. Avoid using negative statements about what you DON’T have…and make sure to refer to the verbatim basic qualification.
Build the sentence into the 1st paragraph if you relate to a passion/value.
Example: Exercising my passion for giving back to the community, I coordinated the 2015 Youthcare dinner auctions, which included project and resource management, ensuring that the event operational costs were on budget and donation goals were exceeded; I believe this sets me up for success with the event management aspect of this role.

Build the sentence into the 2nd paragraph if you relate to work experience… without the negative.
I gained strong understanding of Six Sigma through mentorship with one of the company’s leading black belt instructors during the six workshops we co-facilitated.
Stay positive and frame the statement about your related experience in a way that relates to the actual requirement. 

Am I risking having my resume not being read if my cover letter isn't considered strong?

Not likely and I would not count on it. Rather, focus on making sure to apply to jobs where you meet the basic requirements and that your resume effectively conveys this.  The cover letter is what may make you stand apart from those applicants whose resumes look good. So make your best effort and submit a strong cover letter.

Contact Andrew Trappen

Show Notes

  • View your cover letter to be as important as your resume
  • Take the "Goldilocks" approach - not too much, not too little
  • Resumes offer the what, when, where, how
  • Cover letters offer employers a glimpse into the why
  • Use the why as a validation (if you can't find it for that role, move on)
  • Understanding the why doesn't have to be exclusive to job search candidates - do it for your current role as part of your career evaluation
  • Not confident in your writing skills? Check out The Elements of Style
  • 'Why' resources