How do you deal with career issues in your cover letter?

By Sharon Graham.

Just about everyone has to deal with sensitive issues about their career. By including a cover letter with your resume, you can address many concerns and gain a distinct advantage over your competition.

  • A cover letter shows that you are a proactive professional who takes extra effort to present a complete proposal.
  • It displays your respect for the recipient – recruiter and/or employer – by addressing him or her directly.
  • It gives you the opportunity to display your personality, character, and ethics as part of your submission.
  • It can effectively mitigate a number of career issues by shifting the focus to your value proposition.
  • It allows you to concentrate on the future and hone in on how you can address the particular needs of the employer.

Your cover letter reflects your principles and integrity.

So, how do you handle career gaps and gaffes without looking bad?

Never bring up career issues unnecessarily. Talk more about what you can do for the prospective employer than about what they can do for you. Centre your letter on addressing the employer’s needs, not your wants. If you feel that you must address certain serious situations, carefully construct an authentic statement that comes across as professional and optimistic.

Here are some diverse situations where you can address what seem to be awkward periods along your career path. In each case, describe the positives – the things that you did which were real contributions or learning experiences.


Instead of: Took two years off due to a job loss followed by personal issues.

Try: During a sabbatical, focused on personal and professional development.


Instead of: Took a break to travel the world.

Try: Travelled extensively, becoming more aware of global diversity and challenges.


Instead of: Worked for Company ABC for 3 months, Company DEF for 5 months, and Company XYZ for 6 months.

Try: Accepted three interim roles within the industry.


Instead of: Stayed home for five years until my youngest was in kindergarten.

Try: Assumed volunteer roles ranging from fundraising to teacher’s assistant.


Instead of: Quit work to complete college or university.

Try: Held multiple part-time assistant and research positions and gained credibility in the field while earning my degree.


One final point: during your career, you have no doubt encountered innumerable challenges that pertain to the roles you have held and the companies you have supported. Never portray your previous (or current) employers or colleagues negatively.

When drafting your letter, deliver a positive and upbeat message. For example don’t say, “As the hatchet man, I was sent in to clean-up the company, prune out deadwood, get rid of the current executive team, and then sell the organization.” Change the tone of the message to “I was recruited to revitalize and transform a company that had been in business for more than three decades. I restructured and rebuilt a top-performing organization, successfully positioning the company for sale within a year.”

Addressing career gaps and gaffes can be difficult. If you are struggling with how best to approach your situation in your resume, cover letters, or interviews, consider the support offered by a Certified Resume Strategist (CRS). Any of our talented team of expert consultants will be pleased to help you uncover the value in your situation and assist you in articulating it effectively. To find out what options there may be for you, be sure to send along your current resume for an assessment of your situation.

Sharon Graham is CANADA’S CAREER STRATEGIST and author of the top-selling BEST CANADIAN RESUMES SERIES. Founder and executive director of CAREER PROFESSIONALS OF CANADA, Sharon is committed to setting the standard for excellence in the industry. A leading authority on resume, interview, employment and career transition, Sharon provides career practitioners with tools and resources to enable them to provide exemplary services to Canadians.