Read a Free Sample Chapter

Not sure yet if the book is for you? Check out one of the free sample chapters below.

  • Modern Resumes
  • Repat Biz School
  • Start That Blog!
  • On Risk-Taking
  • My IRS Nightmare

One of the biggest hurdles that limit the number of jobs I have been able to apply for in my own search is the tedium of customizing cover letters and resumes for each specific job. I hear so many stories of people saying “I put out 75/108/250 resumes last year before I got a single interview,” and I think to myself

How is that humanly possible, when it took me 17 hours spread over four days, working after the rest of the family went to sleep, just to get a single application package put together?

This has led me to do some deep thinking on the idea of ‘workflow.’ You hear the term thrown around in the lifehack/productivity circles, but I have never once read an article about writing a resume that outlined a process aiming to make the whole thing easier.

I have yet to see an app or program that effectively streamlines the process either, but I think that with trial and error, and the input of HR trainer Adam Czarnecki, I have come up with a relatively straightforward approach that at least lets me systematize the whole process and approach it in a more efficient way.

Before I get to that, though, there a couple prerequisite steps. First, set up a file system that works for you. You want to have a master copy of your resume that is backed up in a few different locations, and make it virtually impossible for you to accidentally overwrite. Since you are likely submitting multiple documents for each position, it makes sense to have a “job apps” folder in your docs files, that is further separated by folders for each organization, and maybe even further by position applied to.

Second, I have yet come up with a way to deal with the tedium of filling out long forms that require cutting and pasting ten years of work history from your resume. USAJobs is notorious for this. It takes hours of typing and copying and pasting to get into an electronic application system that, frankly, is pretty terrible at producing results for job seekers. It helps to keep a plain text file of this type of data to make the copying and pasting easier, or just swear off applying these types of jobs altogether (80/20 principle ya’ll) unless you happen to have a lot of time on your hands.

If you are applying for those types of jobs, then you will probably still be expected to upload a resume, cover letter, and maybe even reference list though, so the following steps might still be useful.

Without further adieu, here is what I’ve come up with:

Job app workflow

  1. Read through job announcement, taking note of likely important keywords such as “collaborates across departments” and “organizes student engagement events,” with a focus on the top three “Duties and Responsibilities” listed. (JobScan makes this quite a bit easier)
  2. Open master resume file from documents folder. Use “save as” to save a new copy of the file to the desktop for revisions without risking overwriting important changes.
    1. File name should be your name, followed by position, then “resume,” as in “Steven Ward Vice Director resume.doc”
      1. Okay to go ahead and create a new folder on the desktop with this job title and organization name as the file name for saving related documents
  3. Go through resume and make best substitutions, along with any revisions needed to make the keywords fit naturally.
  4. Make sure to use most important keywords like “conduct periodic assessments” verbatim, once each. Making sure that it still feels natural. Use synonyms for similar skills.
  5. Draft cover letter using business letter format, but with a focus on authenticity.
    1. including a subject line featuring the job title and where you found the listing.
    2. 1st paragraph — “This is your problem, and I will solve it because I’m awesome.” research org and identify their major challenge they are trying to solve with this position, and draft a 1st paragraph that clearly and immediately demonstrates your knowledge of the problem and how you will solve it. Name drop an inside connection, if you have it. 
    3. 2nd paragraph — “But you don’t have to take my word for it that I am awesome. I can prove it.” Show your ability to deliver with verifiable stories that have quantifiable results as much as possible, although you are not just rehashing your resume.
    4. 3rd paragraph — “My attached resume shows all my awesome experience in solving this exact problem that you are having.” Refer back to your past experience and your resume while showing you did your homework on the company.
  6. Consider creating some kind of ‘deliverable’ to submit with your application package, much as an artist would show off a portfolio. Possible examples: A detailed analysis you wrote up on the company’s app, a mock syllabus you would use for a course you would teach, or a detailed outline of an orientation workshop you would likely be asked to lead as an important part of your duties. Linking to a video screencast or a slideshare is a great way to do this.
  7. Forget about it for 24-48 hours (if there’s a time crunch, at the very least sleep on it overnight).
  8. Proofread again. And again. Show it to a friend. Read it backwards.
  9. Convert all files to pdf, send it off.

As you go through this process a few times (okay, maybe more like a few dozen times), you will start to narrow your focus on certain positions within a narrower and narrower field that have a lot of the same keywords. Make sure you are populating your personal website and social media profiles with these keywords as well, because your prospective employers WILL be googling your name and checking out your various profiles. Do an audit of all of the above and be certain that they present you in a professional, dignified, manner.

Final advice: Trust the process. You will not land the first job you apply for. Accept that as a fact and pour your heart and soul into it anyway. As you go through the whole process multiple times, the process itself will help you to learn which job types are the best fit for you.