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Last updated 9/28/19.
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-page 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 write the best application possible and maximize their chances of getting an interview. Selfishly, I hope to have a higher percentage of good applicants.
The Basics: Make It Easy for the Reader
Assume that I'm lazy, a slow reader, and not particularly bright.
If you make my job (reading applications) easier, I will be more likely to interview you.
If you make me do extra work to read or understand your application, I will be less likely to interview you.
Let me be more specific.
Know Your Audience
The best writing is mindful of its audience. I am writing this blog post for you.
Your application, however, 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). I don't even know you.
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 a hiring manager’s attention.
Customize Your Cover Letter
When you've read a few hundred cover letters in a row, spotting the generic ones and the templates is easy.
If you're sending the same cover letter for every job, you have no chance of getting an interview. If you only customized the letter by mentioning the name of the company once, don't bother sending it.
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 to it.
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.
Ideas aren’t valuable; execution is.
I am far more interested in a candidate's track record of accomplishments than in what they say they will do in the future.
Tortuga has a team of people working on the business five days a week. I've been thinking about Tortuga 24/7 for a decade. Odds are, we've already considered your idea. Without the context of being inside the business and understanding our goals and strategy, most of your ideas won't be relevant. That's fine.
I'm interested in proof that you have accomplished these ideas before and can do it again.
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. Templates are fine for resumes. Resist the urge to use smaller fonts to fit more text on the page.
Pull up your resume. Take two big steps back from your computer. Can you still understand the hierarchy of information (even if you can't read the text)?
If yes, then you're good. If no, get a new template. If a hiring manager pulls up your resume and can't immediately find the job titles and company names, your application will get archived.
If you've had a long career and multiple jobs, focus on the most relevant and impressive ones. For every bullet on your resume, ask yourself if it’s impressive. If it is, keep it. If not, omit it.
I once interviewed a candidate who only listed one or two bullets per job across an impressive career. If you have the right bullet points, that's enough.
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 things you did to fill the time because someone told you to do them. They do not show that you were self-directed or knew what the most important work to be done was.
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 a cog in a machine.
Cut language like "managed," "oversaw," "responsible for," and "in charge of." These bullets describe 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]
This format shows the action you took, the context of why, and how it impacted the business.
For bonus points, list your accomplishments in the same units as your paycheck: dollars.
Tell a Story
Telling a story in as few words as possible is hard. (I should know. This article is 2,600 words.) But humans respond best to stories.
Too many cover letters start with dry facts like name and age. Those don't matter.
Turn your career and life experiences into a story. What’s the common thread? What happened that changed you? What went wrong and what did you do about it? 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 _____.
Please note that you don't need to literally use that format. I get about ten applications per job that use the exact words and format above.
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. These people are often the best candidates. But you will need to do a bit more work to connect the dots for the reader.
Why THIS Job?
Most people submit the same generic cover letter to every job application. The cover letter details their experience and sometimes 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.
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 (now defunct) Medium publication. I write on this website. We put out a lot of information.
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 filter out 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. You will not enjoy working there.
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 based 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 cultural programming and subtle biases for or against different groups in different roles. This is regrettable but true. 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. I am sorry to tell you this, but it's 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.
Please do not cold email me your resume and application or add me as a connection on LinkedIn. I appreciate the effort and interest, but going outside of our hiring system screws up our process and adds work for me. For simplicity, I have a blanket rule to ignore and archive all of those emails.
The exception is a warm intro from a mutual friend or connection.
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 or those perceived as "easy to get." 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. I'm ambitious too. But if you already have your eye on the next role and are telling me about it in your application then you probably 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'm hiring you for. Remote companies hire for impact, not for potential.
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 examples of achieving the objective in the past.
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 occasionally overburdened hiring manager) will help you to land your next interview. Selfishly, I hope that this post will filter out weak and lazy applicants and help the best candidates showcase how great they are.
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.
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