Observations From My Recent Job Search

by Jeff Stein on January 12, 2019

After working as a technical writer at a large software company for seven years, I found myself out of work in the spring of 2018. It had been a while since I last went looking for work, and I was definitely rusty.

In the months that followed, I interviewed with a total of 11 companies. (This number includes the instances where I didn’t get beyond the initial phone interview.) I have a few observations from the experience that I’d like to share with anyone who is interested.


Conventional wisdom says that you should tailor your resume for each job. The logistics can be challenging, but I developed a system that worked out well.

I have a master version of my resume in Microsoft Word. The file name of the master version is Jeff_Stein_resume_master.docx.

Whenever I applied for a job, I copied the master version to a separate file, which I then customized for the particular opening. The file name that I used when submitting the customized version was Jeff_Stein_resume.docx. Afterwards I changed the file name of the customized version on my local computer to Jeff_Stein_resume_[company-name].docx. By the end of my job search, I had a collection of about 40 customized resumes.

I tried to keep the resumes fairly short — no more than one and a half pages. Nevertheless, some of my interviewers seemed to have taken only a cursory glance at the resume. To help out these people, I prepared a verbal summary of my relevant work experience.

Technical Writing Basics

A couple of questions about technical writing came up repeatedly in interviews:

  • What makes a good technical writer?
  • Describe the process that you follow in creating documentation.

Although I consider myself a veteran technical writer, I wasn’t used to explaining such things verbally.

My responses to these questions got better after I purchased and reviewed The Insider’s Guide to Technical Writing by Krista Van Laan. The author does a great job of covering the many aspects of the profession, such as creating doc plans, gathering information, and working with reviewers. The book was published seven years ago, but nearly all of the content is still valid.

Do You Have Any Questions?

Most interviews followed the same format: the interviewer asked me a bunch of questions, and then I was given the opportunity to ask questions of the interviewer.

I did a lot of preparation for the latter portion. After all, asking questions is a key skill for technical writers, so I figured that this was a great opportunity to show how well I can do it.

Some of my questions were meant to demonstrate my knowledge of the company. A couple of interviewers said they were impressed by how much research I had done.

Writing Tests

Two of the 11 companies had me do writing tests.

One test involved reviewing a series of diagrams that showed how to create a paper airplane. I then had to translate the diagrams into a written procedure. This test reminded me of an interview from many years ago, when I was asked to document the procedure for making a peanut butter and jelly sandwich.

I have heard about writing tests that are more rigorous. Amruta Ranade of Cockroach Labs wrote a nice blog post about the approach that her company uses.

Dealing With Rejection

The emotional aspect of searching for a job should not be ignored.

If you’re not comfortable with rejection, it can be a tough road. The first interview I had was for a job that sounded great, and I felt quite discouraged after not being selected. Over time, I developed a thicker skin and did a better job of moving on when a company said no. Sometimes I thought about what actors have to go through, going to audition after audition, the great majority of which are not successful.

The Result

After months of hard work, I finally got a job offer. My new job is similar to what I have been doing in recent years, but with a few interesting differences.

While I can’t say that the search was enjoyable, I did appreciate the opportunity to learn about so many companies, as well as getting to hone my interviewing skills.

{ 1 comment… read it below or add one }

Fifi Klein December 23, 2020 at 11:32 am

Hi Jeff — I came across your observations from almost two years ago and wanted to thank you for sharing them. I think that everything you discussed is still applicable and useful, even in these especially challenging times. I hope you’re still enjoy the results of your search!

Thank you!



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