If you’re being smart about your job search, you’re tailoring your resume and cover letter for each company you are applying at. If you’re really smart, you’re not making that obvious to the person receiving the resume and cover letter. This is a simple matter of how your organize your files on your computer.
Bad:
- /jobsearch/cover_letter.pdf
- /jobsearch/resume.pdf
One resume. One cover letter. If you’re only applying for one job, having one resume isn’t too bad, especially if it is a well designed resume. But your cover letter should be tailored to each company you are applying at and you should have an archived version of each as well.
The other big mistake here is that the person’s name isn’t included in the filename for either document, which gives it a very good chance of getting lost in the shuffle. Especially if the reviewer organizes things electronically.
Okay:
- /jobsearch/john_doe_cover_letter_design.pdf
- /jobsearch/john_doe_cover_letter_webdesign.pdf
- /jobsearch/john_doe_cover_letter_marketing.pdf
- /jobsearch/john_doe_resume_design.pdf
- /jobsearch/john_doe_resume_webdesign.pdf
- /jobsearch/john_doe_resume_marketing.pdf
This is actually much better. John’s full name is included in the filename for both resume and cover letter and he is creating multiple versions of each file based on the different jobs he is applying for.
Better:
- /jobsearch/design/john_doe_resume.pdf
- /jobsearch/design/john_doe_cover_letter.pdf
- /jobsearch/marketing/john_doe_resume.pdf
- /jobsearch/marketing/john_doe_cover_letter.pdf
- /jobsearch/webdesign/john_doe_resume.pdf
- /jobsearch/webdesign/john_doe_cover_letter.pdf
Here is where a simple change in the way John organizes his files can start to payoff. It’s the same set of files as in the last list but its no longer obvious to the person receiving the files that he is applying for different positions. Why does that matter? It’s the difference between hiring someone who does something well and is passionate about it versus hiring someone who does lots of different things and, well, they really need the job.
Best:
- /jobsearch/company-a/john_doe_resume.pdf
- /jobsearch/company-a/john_doe_cover_letter.pdf
- /jobsearch/company-b/john_doe_resume.pdf
- /jobsearch/company-b/john_doe_cover_letter.pdf
- /jobsearch/company-c/john_doe_resume.pdf
- /jobsearch/company-c/john_doe_cover_letter.pdf
This is the cream of the crop because it works whether he wants to specialize in something as specific as Interface Design or he is just looking for something creative. It also reflects the high level of detail he is putting into his job search. Because he should be paying a high level of detail. He should be researching each company he applies at so that he can tailor his resume and cover letter to them. He should be dropping one or two relevant facts about each company in their respective cover letters to demonstrate that knowledge.

