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There are many ways to write a cover letter, but one caught my attention recently. A young man I know, son of a friend, got a job offer by using a cover-letter strategy that seems counterintuitive: He bad-mouthed an employer’s product.

First, let me give you a little background to set the scene, while protecting my young friend’s identity. I’ll call him Jack.

Jack has a bachelor’s in computer science, and at age 23 he has just earned a master’s degree in a field that makes a lot of use of computers. While doing the coursework (online) for his master’s, he held a full-time job in this field. He has worked part-time in this same field since high school. This means Jack already had a pretty strong resume to bring to the job search.

He also used a good strategy for uncovering jobs: Rather than look only for posted jobs, he wrote directly to the kinds of companies that employ people with his background. One obvious target was the company that publishes the specialized software that he uses every day on his job. By doing some online snooping, he was able to identify the head of HR and find that person’s e-mail address.

I generally advise against contacting HR and instead suggest writing directly to the head of the department where you want to work. But Jack got good results with his method.

And perhaps the key to his success was that he concluded his cover letter by writing, “I HATE your software. Let me help you make it better.”

The head of HR phoned Jack and talked about what Jack disliked (and liked) about the software. This gave Jack a great opportunity to demonstrate his command of the software package and his understanding of the features that contribute to a good user experience. The initial phone conversation led to a few Skype interviews, and eventually the company offered him a job doing software testing.

In the end, Jack decided not to take this job. One important reason for his decision was that the employer is in a very distant state, and Jack (who has lived at home until now) is presently interviewing for a job closer to home. He also was not certain he would like to do software testing.

But the lesson from his job-search experience is still valid, and it applies to interviews as well as to cover letters: Sometimes the best way to interest employers is not to tell them what they want to hear.

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