Archive
What I Would Look For In A Cover Letter
Recently I wrote about how my approach to cover letters changed during my recent job search. As part of that, I was asked what I would look for in a cover letter.
What I Look For
You’ve put the effort into writing a cover letter. Let’s make sure it delivers on that effort.
- Why You Want The Position
Clearly, everyone seeking a position would like a job for some reason. In this troubled job market, people need to be less selective. That’s understandable. But if you can come up with a compelling narrative for why you are interested, that’s a plus. I have a deep background in business marketplace search engines. If I am applying for a position oriented on search, I open with that relevant experience and my interest in those types of systems.
- Why You Will Succeed In The Position
These first three points are all similar, but have different framing. Take this opportunity to articulate why you will be successful if we hire you. It could be your experience, it could be your excitement about what the position will work on, it could be your drive and ability to learn, but make a case that you are going to succeed.
- What Are Your Relevant Strengths
You have strengths. You have experience. Not all of it will be addressable in depth on your resume. Take this opportunity to include a sentence or two for strengths that are directly relevant and will be helped by expansion. This is not for checklist items such as how much experience you have. For example, when positions mention strong communication or strength in mentorship, I use this opportunity to surface my bar raising roles at Amazon for both document writing as well as engineering manager onboarding.
- How Do You Communicate
Most resumes don’t have the space or the context to provide a chance to showcase communication skills. A cover letter provides a chance for you to show how you communicate, to surface your personality. I would not exclusively use AI for this reason; a seasoned communicator will know when you use it and will know it’s not representative of you.
- You Know Who We Are And What We Do
Hopefully you are interested enough to know who we are and what we do. Take this opportunity to tell the hiring manager what about the company resonates with you, and show that you are willing to take some initiative as you target your job search.
- A High Level Sense Of Who You Are
Inject some of yourself into your cover letter, so that the hiring manager can get a read on who you are. Hopefully my cover letter reads the way I want to come across in interviews, as a calm, confident, competent candidate.
What I Don’t Look For
There are things that I will not look for, or hold against a candidate. I don’t believe in mythical checklists or hidden gates that candidates need to be aware of. I’m a big fan of transparency, and won’t reject a candidate just because they aren’t aware of my preferences, especially if those preferences aren’t publicized.
- Personalization
I have seen suggestions that candidates should deeply research the personnel responsible for the position, including the recruiter and hiring manager. I have seen suggestions that cover letters that aren’t addressed to a specific person should be rejected.
Many positions don’t have this information, and even if they did, that has no bearing on whether or not the candidate is qualified for the position and falls into the category of hidden checklist. I address my cover letter as “Dear Hiring Manager”, and that’s acceptable in my view.
- Deep Research
It’s great if you understand what the position requires, have a general awareness of what the company does, and a general awareness of what the company values are should the company articulate them publicly. I don’t expect more than that.
- Appropriate AI Usage
AIs are writing cover letters a lot nowadays, along with other artifacts involved in the hiring process. I can generally glean whether or not writing was done with AI. If I feel like the entire thing is AI generated, that might give me pause; but I encourage candidates to use AI to clean up their writing and narratives.
- Perfect Writing Mechanics
I’ve been a Doc Bar Raiser for Amazon. I know how to evaluate writing mechanics. I can spot typos and other grammatical errors. I’ve also been in meetings where wonderful ideas or highly deserving promotion documents were picked apart due to writing quality. If a document is poorly written, that can be a red flag. But small typos and grammar errors, I’m inclined to ignore.
- Complete Qualification Match
Much like a screening interview, a cover letter is an introduction. The resume is the appropriate place to evaluate qualification matches; a cover letter should summarize why the candidate feels a resume review or a screening interview is in the best interest of both parties.
My Resume Approach
Once it was clear I needed to find a new role, I took a hard look at my resume, which needed a refresher after my lengthy tenure at Amazon. With the advent of ATS scanning, AI, and the competitive job market, it was unclear what the ultimate purpose of my resume was. Was it to get past the technology-driven screening? Was it to meet some arbitrary format requirement? Was it to just “get in the door” and get a conversation with a recruiter?
The answer to this might have been “yes to all three”, but that’s just not my style. If I’m going to produce a resume, I want it to present me in the best possible light, and be reflective of my values and the bar I hold. My resume should make it clear who I am and what I can accomplish first. At some point in the process, a hiring manager or a recruiter is going to read it, and when they do, I want them to have a clear perspective on my career and value.
With that, I decided to ignore a lot of the conventional wisdom I’d received in favor of creating a resume that felt right to me. The risk of misrepresenting myself in two pages felt greater than the risk of going over page length to get the information correct.
First, I decided to create a template with the full list of skills, experiences, and education, which I would then adjust or trim down as necessary depending on the position. My goal was to be able to create a solid resume in the 3 page length range in just a few minutes. I also created a “standard” version of this template I could use for virtually any position if I didn’t want to tailor it. This was useful for such things as LinkedIn’s Easy Apply, which I did use early on in my search.
I separated management and engineering experience, treating them as equal yet different, which in my opinion, they are. This allowed me to call out the depth of my experience in each, and to list different skills for each. I took the time and space to explain details that are important for each item in the skill list. “Written communication” is great, but “taught more than 2,500 Amazonians effective writing culture” is more impactful and more in line with my overall impact. Nuance can be lost in a list of skills; “technical management” means different things if I’m running a team of 5 versus three teams of 8 each, and I can do both if necessary.
I did my best to get skills down to the first page, but always valued clarity over page length, so if things were really relevant, they didn’t come off even if page length was over.
I then followed that with my list of experience by company and role. For each company, I’d list 3-4 relevant projects, along with the role I played, regardless of title, the project, several bullet points, and the result. Many projects I played more than just the management role. When I was at CoStar, technical managers were expected to code half the time; in many of the projects there I was also the most experienced engineer and did a lot of the design work. So one of those projects would read like this:
Project: Land & Farm Data Imports
Team: Marketplace Verticals
Role: Technical Manager, Principal Engineer, Full Stack Engineer
- Managed the release of a new data import system supporting third party data imports.
- Designed high throughput system maximizing tracking, batching, and parallel execution, including more than 10 million property images
- Participated in implementation of the feature including administrative pages and performance monitoring.
Result: System supported continual import management of more than 750,000 land listing from external data providers
After my experience, I listed my degree. As part of my degree plan, I was awarded 18 certifications between 2012 and 2014. Few are relevant today, but if they are for a particular position, I will include them as part of my education.
With a template listing all the things, I can then make targeted adjustments based on the position’s requirements, often comparing them side by side to my list of skills. In most cases, I can get this down to 3 pages, sometimes 4, within just a few minutes. It was more important to me to have a solid case for getting a phone call that wasn’t just driven by ATS, and to make sure that I did not remove key skills just to satisfy page length.
To be fair, I did incorporate a lot of specific technical feedback I received. My current resume has no dates on it, on the advice that my capabilities were more relevant than timing. In cases where a cover letter was not asked for, and I felt a cover letter would help, I would insert a cover letter as the first page of the resume.
One might suggest this doesn’t fulfill the AI screening requirements, but I think it does. First, if skills are in alignment based on my comparison, that’s a good sign we’ll match. But second, most AI tools I’ve worked with require prompts or narratives, and my resume is richly narrative. I have no data on this, but I assume that if there are no hard page length restrictions, my narratives enhance my ability to match an AI tool.
An online version of this format, without projects and including dates, is found here.
I noticed an almost immediate increase in contacts once I implemented this format and shied away from the shorter, less accurate resumes I originally sent. I’m pretty happy now with how it presents me and will continue to use this as my search continues.
If you are currently looking for a new role, I wish you good luck!
My Cover Letter Approach
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.
Be welcome and true.
Rob Hope 