Stop Over-Thinking and Just Spit It Out

Sometimes our greatest block to communication is simply us and our own mind.  We over-think everything.  I am certainly not throwing stones here or the pot calling the kettle black – I am a major over-thinker.  It’s a blessing and a curse: for coaching this is a great asset – for my friends, they just sigh and wait it out.

But when you are job searching or business building there are often times that you need to communicate with your target audience and it must be done via written communication.  Oh no – the dreaded written word!  Fear not – I’m here to help.

Today let’s take a look at cover letters.  One of the most feared items in job searching, but one of my favorite.  Yes, I actually like cover letters – I love them to tell you the truth.  I know this sounds crazy, but first you have to understand I look at the world a little different than most.  If you have read any of my previous blogs this fact should not surprise you…

To me job searching is a lot like dating.  The resume is the first date where you tell all the great stuff about yourself (but save enough for the second date) to interest the person in going out with you again.  The interview is the second date where you start to get a real feel if it is a good fit.  The job offer is the marriage proposal and the acceptance is marriage.

So where do cover letters fit in?  They are the love letters of old.  Remember way back when in the days prior to cell phones, computers and instant access we used to do this thing called writing.  I miss those days.  As a girl there is nothing better than receiving a hand written note from a boy…ahh, romance how I miss you so….but I digress.

The cover letter is the love letter of old enticing the reader to actually go out with you – i.e. read your resume.  The beauty of the cover letter is you can say pretty much anything you want.  You can draw attention to things that don’t quite fit into the resume or state them in a way that brings more emphasis to a single point than you can fit on the resume.

For example if there was a huge project that exemplifies every single quality they are looking for in a candidate the cover letter allows you to really showcase it specifically.  Or perhaps there is activities in your community leadership activities which you think would help support your professional experience – the cover letter allows you to pinpoint and target exactly what you want the reader to know.

I had a client that was on a championship college football team and held several positions of leadership throughout his professional career.  In his cover letter we basically told the reader that he was no stranger to hard work, leadership and team work beginning with his leadership role on the college football team and then select positions throughout his career.

The biggest stumbling block I think most people have with the cover letter is they don’t know what they want to say.  But, actually, you do.  You want it to say, “Read me, read my resume, pick me, ask me out, invite me for the interview!”  Ok, simple enough – let’s start there.

You want them to pick you – then tell me this – why should they?  Please don’t tell me that it is because you have the experience or qualifications – I need to know more.  Remember the whole dating analogy – you need to woo them.  I could be asked out by two guys who are similar in all ways – their work, their age, their looks, their background etc. but if one is a jackass the that pretty much guarantees I won’t say yes.  Convince them you are not the jackass.

You see, another thing you have to realize is whoever is reading your resume and cover letter is very skeptical.  They probably only believe about half of what you are saying because people lie.  This is why it is important to demonstrate not state.  It is also why it is important that you gain their interest.  Boring does not engage.

If your cover letter could be summarized with “I saw you advertised for this position and I am interested and I am the best for the job” well then that is the same a writing a love letter saying, “my friend said you’re cute, wanna grab a pizza?”  Compelling, huh?

Tell them how you fit their needs, how your strengths match up with their needs and how you would fit into their organization while solving their problems.

Just as I stress on your resume that you must sell yourself don’t stop there – you need to carry this through to your cover letter.  No wallflowers here.  Sell it baby or lose the date.  Another technique that carries through from the resume: do not try to write it in one sitting.  First round you should put it in your own words.  Let it flow and do not worry if it is too long, just write it out.  Spell out why they want to talk to you.  Then you can go back and edit and re-write.  Make it perfect – this counts for everything.

One last note – not everyone reads the cover letter first if at all; however, I always prepare a cover letter.  I do not want to take a chance that the one I don’t send one to is the one that looks at them first.  I have a friend that heads up a company and he reads every single cover letter first for every single position.  If there is one grammatical or spelling error the candidate is moved to the circular filing system.


Lisa K. McDonald, CPRW

Career Coach-Strategist

Certified Professional Resume Writer

Career Polish, Inc.

2 thoughts on “Stop Over-Thinking and Just Spit It Out

  1. Great advice here. For yrs I used versions of a well written but passionless letter. It worked in the past so I kept w/ it. But as the job field has slimmed, I find the letter does not get the bites it once did. So I’m starting over, which has been excruciating. This idea of writing it all out in plain speak, then editing, is an idea that I think will help me break this block. Thanks.

    • Matt, thank you for your comment. I am glad this was helpful for you. This is why I love cover letters: your personality can come through a bit more than it does in the resume; also – you can talk about absolutely anything in the world you want to make yourself stand out and align with the company/position. Take a deep breath, relax and you will do great!

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