Answer to Question 1
Answer: Analyzing your strengths and skills helps you accomplish two goals: determining which jobs you are best qualified to pursue and building evidence of your skills to use in cover letters, rsums, and interviews. While a prior job experience may not directly relate to the specific field of your current job search, the skills that the job requires might. For example, writing, editing, analyzing, and communicating, are all skills that range across many fields and professions, and are highly valued in all. Writing down all your past experiences can also lead you to discover patterns of skills that you weren't fully aware of, or discover common aspects of jobs that you particularly enjoy. This again can help you determine the particular types of jobs you are suited to and interested in. And having a record of all your prior experience and skills is good to have as your career goals shift; what seems unimportant today could be highly relevant down the line.
Answer to Question 2
Answer: Both a rsum and cover letter are most effective when they are customized to show why you are a good fit for the position you are applying for. The easier you make it for employers to see you are a match- by highlighting relevant information and keywords instead of including long exhaustive lists, the more likely you are to make it to the next round. Remember, employers evaluate your materials very quickly to see whether you should be considered for the job. So job descriptions, objectives (if included), and the text of cover letters should demonstrate how you exemplify the particular skills and requirements of the job you are applying for and persuade employers not to reject your application. Your cover letter is a persuasive message that tries to sell your rsum to the potential employer. Your cover letter should not simply restate the contents of your rsum. It should demonstrate your knowledge of the company by showing how your abilities match the mission or goals of the potential employer, which you learn about from the company's website. The cover letter is also a good place to address a skill or qualification listed in the job description that you are lacking. Instead of exaggerating your abilities, you might try to reduce resistance to your persuasive appeal. For example, you could subordinate a qualification you are missing and then emphasize what other skills or experience compensate for this and qualify you for the position. Your cover letter should indicate that your rsum is attached to the email or enclosed with a postal letter.