Question:

Why do you need to write a cover letter to get the non-profit Dream Job I saw advertised?  Can’t the new employer get all of the information needed from LinkedIn and the Internet?

You are correct.   Today, we have access to much more information about candidates than before.  At least, the career information is readily accessible through social media and LinkedIn, etc.  However, what is posted may not answer many questions that come up, particularly in senior leadership searches. Your cover letter should communicate much more than the chronological listing of career stops, commonly documented in places, like LinkedIn.  It should also be more than a blurb about your leadership goals and how you achieve them.  The really

good cover letter achieves all of that and more: it weaves your biography, sense of mission, and your career accomplishments together as evidence that you would excel at the new role.

If you look at it in this light, your cover letter serves as a kind of “Leadership Passport” that successfully takes you from one career destination to another with a stamp of approval.  I have seen many good cover letters that artfully list career accomplishments and boldly conclude that the accomplishments, standing on their own, indicate that the candidate will be great for the role.  These kinds of letters advocate the candidate from one perspective. However, the person and the personality are altogether absent.  Reading one of these, you feel as though you are reading the ingredients of a cookie batter.  It all sounds as if it will make a great cookie, but you still can’t be sure.  You don’t quite know how the elements combine and what holds them together.

I have also read good cover letters that emphasize leadership philosophies and leadership development courses and the numbers of teams managed in the past.  What is absent from these descriptions is a sense of mission and concrete accomplishments.  Other letters will list the operating philosophy of the leader in question (“I am an adaptive leader”).  Then, they will list a few accomplishments (I raised $30M during my first year at Humboldt, Charities Inc.), and end by asserting that the candidate should be hired.  Except, what does it mean to be a “certain kind” of a leader?  How did the $30M come in? Was it a one-time gift or bequest? Was it the result of multiple positive acts of sponsorship?  This kind of detail matters.

None of these approaches will generate an exceptional cover letter.  The answer is simple:  they lack “heart.”  The printed word can be inviting and warm.  It can communicate energy, personality, and strong – not offensive—perspectives.  The best cover letters leave the reader feeling that he or she has spoken with thinking, welcoming person who is happy to explain how he or she will help to build or even to transform an organization.

This kind of letter takes time to draft.  It begins by outlining in words the essentials: who you are as a leader, a brief outline of past challenges that resemble the current one, and then a sincere statement of why the new role means something to the person drafting the letter.  This goes beyond statements about how “great” the mission might be or how much it has grown over the past few years.  This really goes to how you, as an individual, see yourself fitting in and offering thoughtful guidance to the organization.

The tone has to be just right.  Even if the organization is having a difficult time, you cannot sound (nor be) the know-it-all with the silver bullet.  At the same time, if you appear to be too wishy-washy or indecisive, this will not recommend you for the position.  You will need to communicate that, although you like to gather data, take input, and calibrate, you are comfortable making tough decisions that will take the organization to the next level.  Drafting this kind of letter requires knowledge of the organization you want to lead and tremendous self-awareness.  To get that level of knowledge may require doing research on the existing politics of the organization, current buzz words, and areas of sensitivity.  None of these subtleties will be addressed when you hurriedly copy chunks of your biography, quote the position description, and repeat that you believe you are competent for the position. A good letter goes beyond 990s, Annual Reports, and website one-liners.  A really good cover letter will be a snapshot of you.  Like a Passport, it will identify you in a way that will make others recognize you on sight.

What makes this organization special to you?  What do you bring to the table that no one else does? 

It is understandable why many candidates shy away from composing cover letters.  They market you, advocate your readiness for the role and reveal your deepest goals and motivators.  It can also be challenging to craft multiple really good cover letters in a short span.  To draft this kind of letter you must be genuinely sold on the mission and convinced that you, and only you, can safely guide it to the next tier of visibility, impact, and service.   If you really want that Dream Job, then take time out to explain why you are, really and truly, the Dream Candidate.

Karen Alphonse is ExecSearches’s Senior Executive Consultant and provides cover letter writing and job search coaching services.  Sign-up for a job search coaching appointment.