The Cover Letter Equation

The Cover Letter Equation

You can find tons of articles on why cover letters are dead and why some people still rely on them more than ever. We are going to look at both sides of the equation to draw insights and propose some solutions.

Why does a hiring manager typically ask for a cover letter?

To assess if an applicant understands the position and why their experience is a match

To allow an applicant to express their interest in the company and team culture

To assess an applicant’s writing and communication ability/style

Allow an applicant to give additional color about themselves not captured in a resume

What makes a great cover letter?

Research into the company culture, the position, the team, the hiring manager and what problems this role will be working on (this should take 2-3 hours if done properly). Great example here by Lisa Siva at The Muse.

Time to carefully craft the letter on how my experience/skill set makes me the best choice to help solve these problems and be a great fit on a team (30-45 mins)

What is the return on investment on time spent writing a cover letter?

Let’s say conservatively it takes 2-3 hours to make a great cover letter, assuming you don’t have any connections in the company, never mind tailoring your resume. This includes scouring social media, news sites, LinkedIn, etc. for what you hope is relevant and up-to-date information.

You spent 2-3 hours, you submit and hear nothing back, was this worth it? Doing this for one job at one company adds up to a lot of time and limits your ability to market yourselves to multiple opportunities. Here are some questions I imagine you might have at this point in the process:

  • If my resume was reviewed by someone or parsed by an ATS (hopefully correctly), did it have all the keywords to get to the phase where my cover letter will be read?
  • Will someone qualified actually read my cover letter for more than 30 seconds? Will they be in a good mood when they read it?
  • Will I ever get feedback on my cover letter (VERY unlikely)? Where could my cover letter have improved? Did it make a difference?
  • Was my resume bad or was I just a bad fit?
  • Do candidates that were referred have to write cover letters? Should I have spent that time trying to network?

Hiring Manager Solutions? (to save everyone time)

Ask for a resume or assessment, THEN ask for a follow up letter of interest/cover letter for the candidates you are interested in. A written 1st round interview!

A resume is expected to be tailored to the position, can inferences be drawn or technology used (sure, AI, why not) to infer from my experience/skill set that I can tackle the particular problems the position is being hired to solve that may not be specified in the job description.

Culture and personality assessments. They are useful but continuing to evolve, they still have a ways to go to be accurate at scale.


Nothing about the job search or hiring is easy, I think we all need to remember that we have been or can be at any point on both sides of the equation so it’s fair that we consider everyone’s time equally valuable. Rethinking why and how we utilize the cover letter is a great place to start.