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My Cover Letter Approach

January 8, 2026 Leave a comment

As I’ve been involved in my search for a new role, I’ve taken several different approaches to cover letters. I’m going to outline what I am currently doing and my rationale for doing so.

One of the challenges of preparing resumes or cover letters has been the depth and breadth of my experience. I spent time as a long term engineer, as an engineering manager with a high percentage of hands on coding expected, and as an engineering manager not expected to code but to be firmly involved in technical processes and decision making. That can make things like “tailored” details on resumes difficult. I felt that it was difficult to adequately state what I perceive my value to be.

I wanted to arrive at a repeatable, scalable process that would take just a few minutes for each job posting. I wanted the documents I prepared to adequately represent my career and qualifications. I needed speed and ease as I, like many of my colleagues, cycled through hundreds of applications.

As of this writing, it’s up for debate if my approach will ultimately be successful. I do think it has managed to get the attention of quite a few companies that might not have otherwise noticed. Responses to those applications seem to be better. During several interview cycles my cover letter was referred to as a resource for the conversation.

There were several general sentiments I heard when this journey began. There was a predominant feeling that cover letters are never read. It was suggested that even though they weren’t read, they couldn’t necessarily hurt. They could be viewed as a tiebreaker should recruiters or hiring managers be choosing between strong candidates in this highly competitive market.

After a couple of weeks of choosing to ignore cover letters, since the prevailing wisdom is they were ignored, I actually decided to completely change direction. If cover letters are never read, except in rare instances, I could do what I want with them.

I chose to use my cover letter to surface all of the information I couldn’t fit on the resume I was including with my application.

I recognize this flies in the face of conventional wisdom, but, hey, if no one’s going to read it….

¯\_(ツ)_/¯

Thus, I went from no cover letter to a 9 pager that includes:

  • Page One: A targeted cover letter, with mostly templated information, summarizing my career highlights and the value I bring. It contains a paragraph introducing me; a paragraph on my general philosophy; a paragraph on what I’ve done as a manager; and a paragraph on what I’ve accomplished as an engineer. Within two or three minutes, I can adjust content, add specific information, and optimize for the position I am interested in. A variation of that cover letter can be found here.
  • Page Two: A portfolio of the websites, systems, and companies that I have had an impact on. Many times candidates are asked for this portfolio, and I automatically include it in my cover letter, just in case someone opens it and decides to scroll past the first page. That portfolio can be found here.
  • Pages Three through Nine: A list of the critical projects I’ve delivered, and my role in delivering them, along with the results. I’ve missed a few here and there and update this list as I recall things. For example, in a recent interview I talked about a feature I built into one of my web portals that would include the entire logging history of the system into the web page, piggybacking and enhancing Microsoft .NET’s native tracing feature. I’m going to add that to the list soon.

Having the list ready to go gives me a couple of other efficiencies.

First, if a company doesn’t ask for a cover letter, and I really want to send one, I’ll simply include it as the first page of my resume by copying page one from here and adjusting it for those needs.

Second, I have my list of projects ready to go, already in consistent format with my resume. I then pick and choose the relevant projects from this list to include on the resume I will send based on the company’s requirements.

So, while I am tailoring my resume, I’m not rewriting narratives or reorganizing. I can be ready to apply to any position within 5-10 minutes with a consistent, complete narrative.

If you are also searching for a new role, I wish you good luck.

Categories: career, Informational, Work Tags: , , ,