Do I need to send a cover letter with every resume I submit?
There are times when cover letters are not necessary (i.e. on campus interviews arranged through Office of Career Services, Job Fairs, or other special circumstances). In most cases, especially when you initiate contact, it is a good idea to include one. If ever in doubt, send a cover letter with all resumes.
Doesn't the cover letter repeat the same information listed on my resume?
The cover letter is usually read before your resume and may highlight or refer to specific information on your resume. More importantly, the cover letter allows you to state why you are interested and explain in more depth your responsibilities, roles, skills. It should be interesting to read and unique to your experiences and interests.
Will I come across boastful if I write about my strengths? I feel uncomfortable "bragging."
Like a resume, a cover letter is a marketing tool. It is a critical part of the job search process. It is important to sell yourself and your talents in your cover letter, but the biggest challenge might be finding the right balance between being modest and sounding over-confident and boastful. Be careful. Don’t say anything that you can’t back up or support. At the same time, allow yourself to take credit for your past accomplishments as well as your skills and talents. Do not simply state your strengths; give concrete examples of how you have developed skills and used your talents. Allow other people to proofread your letter and be willing to listen to their feedback. If you do not articulate your confidence, how will the employers know they have the "right" person for the job?