Last updated 7/30/19.
I’ve read almost 800 applications, across three positions, in the last month. I’ve interviewed 19 people on Skype. I’m exhausted.
The first pass through was the hardest: half-empty application forms, cover letters filled with grammatical errors, three-pages resumes, and plenty of people who clearly had not read the job description.
Being on the other side of the hiring process has shown me the mistakes I once made applying for jobs.
I thought my cover letters were short and to the point but never considered that the recruiter was reading mine in the middle of hundreds of others. I assumed the recruiter was carefully reviewing my resume and savoring every word. I was wrong.
I’m writing this article so that future applicants can put their best foot forward and not waste their time (or mine). The article should be helpful to you, but I’m writing it from a totally selfish place.
How do you write a compelling application and avoid being archived?
The Basics: Make It Easy for Me
Assume that I am lazy, a slow reader, and not particularly bright.
If you make my job (reading applications) easier, I will like you more.
If you make me do extra work to read or to evaluate your application, I will like you less.
Let me be more specific.
Know Your Audience
Your application is about me, not you. I know that sounds backwards.
I, the hiring manager, am your audience. I care about my business. I do not care about you (yet). You are a stranger taking up space in my inbox and time on my schedule. Tell me why you’re worth it.
Appeal to my self interest and tell me what you can do for me. That statement sounds selfish because it is. But this is the best way to get an employer’s attention.
All good writing is mindful of its audience. Resumes and cover letters are not exceptions.
I will hire you if you can grow my business or make my life easier. I will not hire you just because it’s your dream job.
Customize Your Cover Letter
When you've read a few hundred cover letters in a row, the generic ones and templates become obvious.
If you're sending the same cover letter for every job, you have no shot. If you customized the letter by mentioning the name of the company once, don't bother.
You should write a completely custom cover letter for each job that you apply to. If you don't think a given job is worth the extra effort, don't apply.
Get the Interview, Not the Job
Your application can only get you the interview, not the job.
You will not get hired based solely on your application. Have you ever been hired without an interview? No. Assume you will have another opportunity to share details about your work history.
What are the most important accomplishments that make you an obvious candidate for an interview? Put those in your application. Take everything else out.
Show, Don’t Tell
Don’t bother with a teaser like, “I have some great ideas I’d like to share with you by phone…”
I might be cynical, but this line feels like a cheap ploy to get an interview without having to actually have those ideas. You have as much time as you need to write your application. Pitch me an idea. Even if I don’t hire you for the job, I might pay you to follow through on your idea. Or create a new role for you.
Ideas aren’t valuable; execution is. Share your ideas.
You can really impress me during the application or interview stage using Ramit Sethi’s Briefcase Technique.
Play the Hits
Your resume should be a one page summary of your career highlights.
Do not write an exhaustive list of every task you’ve ever done at every job you’ve ever had.
Keep your resume to one page. Do not let it become a wall of text. To fight this urge, use a visually-pleasing resume template. Resist the urge to use smaller fonts to fit more text on the page. If you've had a long career and multiple jobs, cut the least relevant ones.
For every bullet on your resume, ask yourself if it’s impressive. If it is, keep it. If not, omit it.
List Accomplishments, Not Tasks
The reason your resume is so long is because you are listing tasks, not accomplishments.
A bullet list of tasks reads as:
I did a task that took up time in my day so that I could get to 5pm and leave. I did this task because someone told me to. I did not bother to measure the outcome or consider if this task was worth doing.
When I’m hiring, I want to hire someone who can accomplish the goals for the position and who is uniquely suited for the role. Describing your work history as a list of tasks makes you sound like any other cog in the machine.
Weak bullets use words and phrases like "managed," "oversaw," "responsible for," and "in charge of." These clarify the scope of your role but are not accomplishments.
Strong bullets start with verbs, contain numbers, and are tied to business outcomes.
Here's a mad lib you can use:
[verb] [aspect of business] by [number or percentage] in order to [business goal]
For bonus points, list your accomplishments in the same units as your paycheck: dollars. Unless, of course, you want paid in Instagram followers.
Tell a Story
Telling a story in as few words as possible is hard. (I should know. This article is 2500 words.) But humans respond best to stories.
Too many cover letters start with dry facts like name and age. I don’t care about those.
Turn your career and life experiences into a story. What’s the common thread? What happened that changed you? What’s next for you?
Here's the generic structure of a story:
Once upon a time _____.
Until one day _____.
Because of that _____.
Because of that _____.
Until finally _____.
Now every day _____.
A story is easier to follow and to remember than a series of unrelated paragraphs about your work history. Like any good writer, you should leave out the stuff that doesn’t advance the plot or develop a character.
A story is especially important if you aren’t an obvious candidate for the job or if you have a non-traditional career path. If your work history appears unrelated to the job that you applied for, tell me why you’re a fit anyway.
Why THIS Job?
Most people submit the same generic cover letter to every job application. The cover letter details their experience and vaguely alludes to the type of job that they're looking for next.
The best companies don't want to know why you want a job, they want to know why you want this job. Be clear about why you want this job at this company.
Carefully read the job listing and the company's about page and blog.
Do you understand what it's like to work there? Are you a good fit? Tell the hiring manager why.
Tortuga is a unique place to work. We're remote. Most of the team works relatively autonomously. We're diligent about hiring teammates who share our values. We have a company blog and defunct Medium publication. I write on this website.
Do your homework, assess the fit, then tell me why you want to work here and, even more importantly, why you would thrive at Tortuga.
Caveat: If the company's website and job listing aren't clear about what it's like to work there, don't apply. The best companies understand their culture and use it to their advantage. Culture will help to attract the right candidates and to repel the wrong ones.
Amazon is clear about its frugal, hard-driving culture. You may or may not want to work in that environment, but at least you know the deal and can make an informed decision about applying. Stripe does a great job of describing its culture in Life at Stripe.
If a company cannot clearly articlulate its culture to applicants, the company may not understand its own culture.
Don’t Share Personal Details
Do not start your resume with, or even include, demographic information like your gender, age, marital status, or number of kids.
Many demographic questions are illegal to ask during interviews. Let’s stay as far away from those as possible.
Demographic details are irrelevant at this stage. I am doing my best to judge candidates on their skills and work history.
Studies have shown racial bias based on the name on a resume. Even the most enlightened of us may have subtle biases for or against different groups in different roles. Leaving out your demographic information helps me assess you solely on your merits.
Most applicant tracking systems (ATS) use your email address to connect your social media accounts and profile photos to your job application. For privacy and to help counteract any potential biases in hiring, we use the Candidate Privacy Settings in Workable, our hiring tool, to select "Never show candidate photos" and "Do not show links to candidates social profiles."
When I have hundreds of resumes to read, I need filters. Not every resume gets the same level of attention and careful reading. I don’t have the time. This is a fact of hiring, and you should know the truth.
This section is dedicated to the red flags that tell me I can stop reading and archive your application.
Not Following Application Instructions
Most companies use an ATS to manage recruiting, interviewing, and hiring. Use the application form provided. Follow the directions. Answer all of the questions, even the optional ones.
I do not appreciate strangers who cold email me their resume instead of going through our application system. Going outside of the system screws up our process and adds work for me. Also, please don't add me on LinkedIn.
Poor Grammar or Spelling
I’ll give you one typo because I’m kind and generous.
Proofread your application. Read it out loud to yourself. Ask a friend to read it and give feedback.
Not taking the time to review your application shows me that you don’t care about the job. If you don’t care about the job, I don’t care about your application.
Not Providing Work Samples When Requested
If an application asks for a portfolio or links to past work and you don’t have past work to show, don’t apply. You’re wasting the recruiter’s time.
Applying for the Job After This One
I see this most often with entry-level jobs. People say they are applying with the intention of moving up into another role.
Everyone expects to advance in their career and to move up or around every few years. That's fine. But if you already have your eye on the next role and are telling me about it in your application then you clearly don’t care about this role. If you don't care about the role, I can't hire you for it.
Using the Job as a Learning Experience
“I feel like this position would be an incredible learning experience for me.” Be careful using phrases like this, especially if you’re applying to a small company.
Enterprise Rent-A-Car has a training program. Small businesses do not. I cannot pay you to learn how to do the job I hired you to do. Remote companies hire for impact, not for potential.
Pay for your own schooling or learn on someone else’s dime and time, even your own. Big companies are a great place to start your career and learn foundational skills. I did that at Google.
Pay for an online course or do a side project in your free time to learn new skills and to have something to show a prospective employer. If you truly wanted to learn that skill, you would have started already. You wouldn't need me to give you the opportunity. Being a successful remote worker requires initiative. Show some.
Dan Andrews of Tropical MBA put it succinctly in his advice for apprenticeship applicants,
I don’t want to be a ‘big opportunity’ for people. I want to be a ‘natural opportunity’.
I'm referring in this section specifically to the skills needed to do the job to which you applied. Of course, I hope that, if you join Tortuga, you will take on new projects and learn new skills. I will happily pay for and support team members in upgrading and expanding their skills.
Being an Asshole
Pitching new ideas or improvements is helpful. Criticizing what we’re doing now is not.
Trashing a company is not a good way to show that you want to work there. If your application is that obnoxious, no one will want to meet the person who wrote it.
Learning how to critique ideas in a useful way will be valuable in your career.
After spending most of this post bashing what people do wrong, I want to praise unique things that people did right.
Writing to the Objectives
Our job listings use the Scorecard template from the book Who?. Rather than list a bunch of things that the new hire will be in charge of, the scorecard lists Objectives that the candidate will be expected to accomplish.
The strongest cover letters we've received throw out the usual template and, instead, list how the candidate will achieve each objective.
Unconventional Social Proof
The right social proof can show that you’re part of the community or industry where you’re applying to work. Which types of social proof are relevant will depend on the business.
For Tortuga, a travel company, I was impressed by a candidate who linked to an Airbnb host profile and another who linked to a (top-rated) Amazon review for one of our products. A TripAdvisor or Yelp review that specifically cites your great work would also be a positive in the travel industry.
It’s Not About You
I wrote this in the hopes that hearing the truth from a CEO (and occasional hiring manager) will help you to land your next interview. Selfishly, I hope that this post will filter out weak applicants and help the best people to showcase how great they are.
The bottom line is that your application must focus on how you can help the company. Keep that in mind, and you’ll be in the top 1% of applicants.
You can learn more about working at Tortuga and see our open roles on the Join Team Tortuga page.
Author's Note: I promise that I’m not this obnoxious in real life.