Get an inbox full of good cover letters

Imagine a job ad you posted has closed. You begin making the shortlist by skimming through submissions. You notice some applicants have written good cover letters, but most just summarised their CVs. You find an interesting applicant so you pause to re-read their submission. You learn about the companies they’ve worked for, but you wonder if their values will add to yours? You learn about the projects they’ve worked on, but you wonder how they make progress happen? You’ve gained perspective on their experience, but you don’t have any perspective on what they’re like to work with.

Normally you’d seek to understand these characteristics through interviewing, and you should, but leaning entirely on interviewing is exhausting. Shouldn’t the effort of writing and reading cover letters be a way to gain an insightful perspective before interviewing? Why do some people seem good at writing cover letters while others seem to miss? A few years ago I started asking myself these questions. I began to experiment with helping our applicants write good cover letters after seeing this job ad. Cover letters which were relevant, insightful and surprising. Cover letters which showed applicants at their best, even if they didn’t have all the experience.

I learnt you can get an inbox full of good cover letters by letting applicants know what you’d like to see in their cover letters from your job ad. Instead of signing off with “Please introduce yourself by sending your cover letter and CV to…” I tried signing off with “Instead of a cover letter, we’d love to hear your answers to these questions…”. I supplied six, short answer questions which explored motivation, growth, collaboration, and values. These were the characteristics I longed to understand when making the shortlist.

To give you a clearer idea of what I mean here’s an excerpt from a job ad I posted in late 2021 for a Frontend Designer:

Introduce yourself to our team by sending an email to readblindly+f5jni3@emails.readblindly.com. Tell us a bit about yourself and include your CV. Instead of a cover letter, we would love to hear your answers to these questions in the body of your email:

Why are you considering working here and why now?

Would you consider yourself more of a frontend developer, more of a UI designer, or a mix of both? Where are you comfortable today and where would you like to learn and grow in the future?

Have you worked with Ruby on Rails before (If not, that’s OK!)? What templating/technologies have you worked with? Which one was your favourite and why?

You are working on a feature. You feel strongly developing it this way will get a better outcome, but your co-worker who is a full-stack Product Engineer disagrees. What do you do next?

What do you think are the ingredients for building a high-quality app? What does quality mean to you and how do you help maintain it over time? Can you share a proud or insightful moment with us as an example?

Do you have a portfolio or screenshots of previous work you can share with us (If not, that’s OK!)? Link? Attachment?

…and here’s an excerpt from a job ad I posted in late 2020 for a Product Manager:

Please introduce yourself to our team by sending an email to readblindly+f5jni3@emails.readblindly.com along with your CV. Tell us a bit about yourself and imagine our futures together. We’d also love to hear your answers to these questions:

Why are you considering working here and why now?

In the past, what have you done to gain confidence that the ideas and features being put forward for development are good bets?

Imagine the project team is about to finish an exciting new feature. It has the potential to grow earnings for the organisation that use it, but it will require them to make some tough changes to their internal processes. Working with our marketing and customer relationship teams, what tactic might you use to help the organisation understand and take on the new feature?

Tell us about an experience where an idea that you turned into a feature and shipped ended up being a mistake. What did you learn from that experience and what would you have changed if you could go back in time?

Briefly describe some of the previous roles you’ve had (It does not have to be a product role). What are you are most proud of achieving while in that role? What did you learn that you’ve used in other roles? What would you do differently now if you had that role again?

…and here’s an excerpt from a job ad I posted in mid 2020 for an IT Support Specialist:

A description of a great support/customer service experience you had recently and what made it great.

A time you taught yourself a new skill to complete a job or project.

A guide to making your favourite meal (Or maybe the only meal you can make?)

All job ads I’ve posted since mid 2020 have signed off with questions. Originally they were in addition to the cover letter, but now they’re in lieu of the cover letter. I’ve experimented with asking 3 questions, 5 questions, and 6 questions. I’ve experimented with asking general questions and specific questions. I’ve learnt to:

Ask 5-6 short answer questions. Any less and you don’t get enough breadth. Any more and it’s too time consuming for the applicant to write, and for you to read.
Cover a spectrum of characteristics. It doesn’t matter if the questions themselves are general or specific. Spend them wisely and don’t double up.
Draw inspiration from recent experience or problems. If it’s an existing job ask someone in the job. If it’s a new job consider the circumstances of how you learnt about the problem.
Keep questions relevant. Don’t assume you can copy questions from an old job ad for your new job ad.
Write questions yourself. Don’t leave it to someone else.
Emphasise to applicants that you, the hiring manager, who is also a human, will read their submissions.
Give gratitude to applicants for taking the time to apply, irrespective of your evaluation.

When it comes to reviewing submissions the first thing you’ll notice is the applicants who read the job ad, and the applicants who didn’t. I decline the applicants who didn’t. The second thing you’ll notice is how comprehensive the cover letters are, and the baseline you now have to compare objectively. I recommend doing a pass on cover letters first to make your initial shortlist, and then go back and do a pass on CVs to make your final shortlist. I weigh cover letters above CVs because of their relevance to the job ad.

When it comes to interviewing applicants, the experience may feel closer to the second interview. Not quite the second interview because you’ve never met before, but not quite the first interview because you’ve already gained an insightful perspective. I recommend using some of the applicant’s answers to go deeper, especially if they are surprising to you.

Next time you post a job ad consider signing off with 5-6 questions and you may get an inbox full of good cover letters. They may help you resolve a tie breaker, or they may help you discover an applicant outside your sphere. Likewise, they may help applicants write more insightfully about themselves. Either way, you’ll be making your shortlist with a more insightful perspective. Feel free to use and mix any of the questions from the above excerpts if they inspire you.

Written by Tate Johnson on 7 Jan 2022. Subscribe to my blog's RSS feed.