Cover Letter Moves That Can Win Over Skeptical Employers

Most cover letters need to accomplish a few simple, universal goals: They need to explain what a candidate wants, describe what she has to offer, and convince managers to hire her instead of another contender in the applicant pool.

But if you have a tricky obstacle to overcome—like a criminal conviction, a long resume gap, or a possible red flag in your job history—you’ll need to offer a little extra something that encourages reviewers to look past any possible perception issues.

Here are a few tips and tools that can help you win over a potentially skeptical hiring manager:

Use euphemisms, and use them wisely. 

It’s okay to say you “parted ways” with a potential employer when you were actually fired and told to clean out your desk by the end of the day. And it’s okay to describe your mistakes as “lessons learned.” In fact, this lets reviewers know that you understand the context of the situation and that you have the resilience and flexibility to use setbacks to your advantage.

Emphasize your general strengths.

If company managers are looking for “proven leaders with eight years of experience in an industry setting,” and you have only five years of experience, then don’t dwell on those missing three years. Instead, focus on your proven leadership. List specific accomplishments in your history that align with this need. Talk about your leadership style and discuss a recent episode in which you led a team to victory or guided a group of coworkers through a period of change.

Emphasize your specific strengths.

Show that you’ve done your research, and describe the specific technical skill sets you possess that might be of interest to these specific hiring managers. Delve into the background of this company and its business model, and determine how your unique skills and certifications might help the organization solve a stubborn problem or expand into a sought-after new customer base.

Know which issues not to bring up…just yet.

Most of the time, there’s no need to use your cover letter to bring up anything that might be an obvious deal-breaker. For example, if you’re going to need a salary that you don’t think this company can afford to pay, wait until the interview (or better yet, wait until you receive a formal offer) before you bring this up. The same applies to handicaps that your employer may not be able to accommodate, geographic obstacles, and other concerns that might get you removed from the running before you have a chance to explain your application in person. It’s okay to diplomatically omit this information until you can present it in a larger context.