Rob Hope

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.