Covering Cover Letters

Straight Answers to Real Questions

Question: I’m a CFO in the food service business and I’ve just started to look around for a new position. I haven’t looked for a new job in quite a few years and I’ve been asking my pals for input on the best way to present myself to prospective employers.
Some of my friends have advised me to draft a new cover letter with every resume I send out, specifically detailing why I’m a good fit for the position I’m applying to. It seems like a lot of work – what do you think?

Answer: It actually depends on the circumstance in which you’re sending out your resume. Are you applying to an ad or online posting? Or are you sending your resume to someone on spec? Or perhaps you have the inside track on a CFO opening.

If you’re applying to an ad or online posting, it’s just good manners to include a cover letter. Personally, I tend to gloss over cover letters and go straight into the resume. If it isn’t obvious from the resume why someone is a fit for the particular position they’re applying to, anything the candidate may have included in their cover letter probably isn’t going to change my mind. That being said, being a headhunter, I’m in the business of parsing resumes; someone with less experience in reading resumes may find the additional information in a cover letter useful when deciding who to interview. So if you’re sending your resume to a headhunter, you can get away with a boilerplate cover letter. If you’re sending your resume directly to the hiring authority, you may want to highlight the skill sets and experience that you think are relevant to the position you’re applying for.

If you’re sending your resume to someone on spec or if you have the inside track on a CFO position, it’s definitely worthwhile to include a position specific cover letter with your resume. When crafting the cover letter, don’t just reiterate what’s already in your resume. Do some research on the company you’re applying to and specifically address the challenges and opportunities that you think will resonate the most with that audience.