The Resume Game: Playing to Win the Interview

Most of us have been there: You’ve sent out your resume to multiple jobs where you know you’d be a great fit, but none of them have asked for an interview. Not one single call back or move to the next round. It can be frustrating and disheartening and you might begin to wonder if something is wrong with your experience. Or you might know that there are weak spots in your professional history, but if you could just get an interview you would be able to explain why you’re still a great candidate.

The thing is, the resume and application process is often not fair, neutral, or even very logical. It’s a system set up to minimize hiring managers’ time and the organization’s hiring risk as much as possible. The sooner you start thinking of it as the game it is, the sooner you can start playing to win the interview.

Identifying Your Obstacles

Many organizations get swamped with resumes for a single job posting, and most of those resumes will not be a good fit for the position. In fact, a large number won’t even meet the basic skill or expertise requirements for the job. It makes sense that hiring teams have tools to make their reviewing process easier and that they, like all of us, can burn out on too much information or complexity. To play the resume game effectively, you have to understand how to go around the obstacles standing in the way of your resume’s success.

Keyword Scanners

When you upload your resume through an online portal of any kind, it’s very likely the organization will run it through a keyword scanner first. Both the upload software and the keyword scanning software can cause all sorts of problems if you don’t understand this part of the game.

If you submit a resume made in design software or even a plain text one that uses a lot of tabs and tables, you’re setting yourself up for failure. Both upload software and keyword scanning software can break your resume beyond recognition, separating columns and lines and even individual words until your resume becomes a giant mess far beyond anything a computer or human can understand. Save the fancy resume for when you have a real human’s email address and avoid pre-formatted templates from the internet like the plague.

Keyword scanners are also looking for particular words, not synonyms of the words or a description that means the same things as those words. Use the same words the job posting uses to get the best results with keyword scans.

Human Fatigue

At the end of the day, hiring managers are humans like the rest of us. Even after the keyword scanner weeds out dozens of resumes, hiring teams have a lot to look through. They will go quickly and they will get tired. If a hiring manager has to think or read much at all when reviewing the resume, you will lose their interest and the interview.

Humans are also scanning for certain keywords and not necessarily processing synonyms or concepts that mean the same thing. This is another good reason to use the same keywords as the job listing, even if you would normally call a skill or process something different.

You should assume that your resume is getting no more than a cursory glance before the person looking at it decides to keep reviewing it or reject it out of hand. In that single glance, your resume must shout that you are not only a qualified candidate, but a pretty impressive one at that.

Red Flags (fair or not)

Hiring teams will weed out resumes for any tiny reason — remember, they’re trying to get their pile down to just a handful of candidates to interview. Some of the reasons aren’t very nice. In fact, a lot of them are complete and utter BS. You can’t fight it though — hiring teams will find another official reason they rejected your resume if asked. All you can do is to use this information to avoid getting weeded out. Reasons you might unfairly land in the “no” pile:

  • Gaps in Work History — Unemployment of any kind, including going back to school or being a stay-at-home parent.

  • Filler Jobs — Non-career positions outside your field you’ve taken to earn income while between jobs.

  • Moving to a New Market — Out-of-town resumes often immediately go in the “no” pile.

  • Changing Careers — Hiring teams can be distracted when your past career experience doesn’t line up with the position you’ve applied for.

  • Switching Industries — If a hiring manager thinks you don’t know the industry, you could be right out.

  • Education Level — You might have 20+ years of experience in your field but the position requires a bachelor’s degree.

  • Not Enough Experience — The job listing says 3–5 years but you’ve only been working 2.5.

  • Age — Just out of school or 50+.

A pretty unforgiving list, isn’t it? It really is a game of making it to the final cut and this is where you have to play the game right back. You can counteract these so-called issues by avoiding shedding light on them in your resume.

Rethinking Your Strategy

In games, there are rules and it’s no different in the game of writing and submitting resumes. Here, though, the company and hiring manager set the rules and you don’t necessarily get to know what they are as you play along. Fun, right? For that reason, your resume game has to be all about strategy.

1. Analyze the job description.

You’re looking for anything you can use to your advantage. Are they looking for certain software or hard skills? You should mention these by their exact name in your resume, no abbreviations or shorthand. What keywords does the description use to talk about the position? You should use this same language in your resume, without outright parroting what the job listing says of course. Keep that keyword scanner in mind. You don’t want to get weeded out just because you used a synonym.

2. Make your resume ridiculously easy to understand.

If someone can understand your resume just by reading the headings and quickly scanning the bullet points, you’re doing it exactly right. Because that’s actually all most hiring team members are going to do.

Don’t feel the need to include every little thing. Feature the highlights from each position and include significant accomplishments that match the job listing. That’s all you need. Avoid the inclination to fill every square centimeter with information. Use two pages if you really need to (if you’re an experienced professional with a long work history, you probably will). We’ve had one-page resumes drilled into our heads, but that’s what leads to nonexistent margins, 9-point font, and no room for the resume or the person reviewing it to breathe.

3. Address the so-called issues.

So maybe you have a gap in your work history or maybe you’re applying from out of town. Maybe you’re 22 and applying for your first job or maybe you’re 55 and looking for the job that will take you through retirement. All of these things can be “red flags” to hiring teams. Don’t raise that flag in your resume. There are ways to downplay anything that might land you in the no pile. Here are some tactices to address the most common resume “issues” I regularly see from my clients:

  • Play with how you display dates— Maybe you only list the number of years you were at a position instead of actual year numbers. This makes it just a little harder to do math and determine work gaps or your exact age — a bonus for you when someone is reading your resume at lightning speed.

  • Decide what comes first — Don’t have the education requirements the job asks for but have a long, successful history in your field? Maybe you want to put your education last.

  • Leave your physical address off — This is the new millennium, who gets job application correspondence via the postal service? If you’re applying to a new market, include in your LinkedIn profile instead. Then you can have the conversation about your move when you’re talking with a real person.

  • Don’t mention filler positions — If you worked a job outside your field for a while to earn some income, don’t list it. It can be distracting from the rest of your experience and raise hiring team eyebrows. If you feel like you gained relevant experience in that job, you can mention that during an interview or briefly in a cover letter.

Playing Your Best Hand

None of these tactics — or others like them — are dishonest. They are a way of putting your best foot forward to land the interview. In a game of poker, you wouldn’t show that you have a card you don’t like. The same goes for the resume game. Once you get in a room with a real person who’s already identified you as a good candidate, you can discuss any of these things — but only if your interviewer brings them up first.

Play the Game, Get the Interview

Really, playing the resume game boils down to speaking the same language as the organization you’re applying to. While you’re removing any potential reasons to put your resume in the “no” pile, you’re also showing that you’ve paid attention to what they’re looking for and that you’re on the same page. And that is an excellent reason for them to offer you an interview.

No More "To Whom It May Concern:" Address Your Cover Letter to a Real Person

It’s hard to begin a cover letter, and I’m not even talking about writing the first sentence. The salutation itself can be nerve-wracking or frustrating or seemingly unimportant enough that many applicants resort to “Dear Sir or Madam” or “To Whom It May Concern.” Often you don’t really know who will be reading the letter, and you’re probably writing a lot of cover letters all at once. Addressing generic “whom/Sir/Madam” may seem like a catch all — the quickest and safest thing to do.

It’s not. Well, it may be the quickest, but if you take the time to try to figure out who is on the receiving end of your letter, you’ll instantly prove a few things to a prospective employer.

Taking the Time to Find a Name Proves…

1.     You did your homework. You looked into the company enough to know who may be making the hiring decisions for the team you’d like to join.

2.     You care about this particular job. You spent the extra time to find a name, which means you probably really do want to work with the company.

3.     You’re not just sending the same form letter to everyone. The whole “whom/Madam/Sir” thing makes your cover letter look like a template you’re sending out to every job to see what sticks. Assuming you’re not doing that, addressing your cover letter to a particular person suggests that the rest of letter will also be relevant to particular company and position.

Plus, people like to read letters addressed to them instead of to some general person. Don’t you throw away mail addressed to “[Insert Name] or Current Resident?” I know I do, because 99.9% of the time I’ll be wasting my time reading it. The same applies to generically addressed cover letters.

Finding the Name

Finding a specific person’s name can be a little time consuming, but you’re already taking the time to write a cover letter and send an application. You might as well make sure you’re giving yourself every advantage, and this is one of the easier strategies to make yourself stand out. There are multiple ways to find the right person’s name. Some are easy and some will take a little sleuthing:

In the Job Posting

Lucky! If the job description mentions the hiring manager or department manager by name, your job is done. (And you have absolutely no excuse not to address your cover letter directly to that person.)

Make LinkedIn Your Friend

A large percentage of the time, LinkedIn can help you find the person you need. Start with a keyword search. If you know the name of the department you’d be working in, try a search like “[Department Name] Director” or “[Department Name] Manager.” More often than not, someone in the first list of people you get will make sense as someone to address the cover letter to.

If no one in the list looks like the manager or director of the department you’d be working in, try a broader search for the company hiring manager. Try a search like “[Company Name] Hiring Manager” or “[Company Name] Talent Acquisition” or “[Company Name] Recruitment.” You’ll probably be able to find someone in that list that would likely receive your cover letter.

Pro Tip: I’ll tell you a secret. It doesn’t matter if you pick the exact right person who’s going to pick up your cover letter and read it. It’s likely many people will read it over before an interview anyway. As long as you get close and find someone who’s extremely likely to have a say in the hiring process, you’ve done what you need to do.

Pick Up the Phone

Every once in a while, it can be all but impossible to find someone to address your cover letter to. Now, I’m not suggesting you call up and ask about your application, especially if the job posting specifically says no phone calls. Instead, just call the main number and ask who manages the department you’d be joining. You’re almost certainly going to get a name, and the receptionist is not going to tell on you for asking. (But even if he or she does, making the effort to call works in your favor, not against it.)

Address to a Group or Job Title

If at any point you’re really unsure about the person you’re addressing, or you’ve gone through all the ways to find a name and come up dry (it happens), addressing your cover letter to a group or a specific job title is still better than using “whom/Sir/Madam.” Some examples:

  • “Dear [Person’s First and Last Name] and [Department Name] Team”
  • “Dear [Manager or Director Title]”
  • “Dear [Department Name] Manager and Team”
  • “Dear Hiring Manager and [Department Name] Team”

Addressing your cover letter to a group or job title is a last-ditch option, but it’s still going to set you apart leaps and bounds above other applicants using the generic “To Whom It May Concern.”

Opening Strong Could Help You Get the Interview

It’s only worth writing a cover letter if it does what you wrote it to do – set yourself apart from other applicants. Starting the letter off by showing that you took the time to figure out who might be receiving it is a powerful opening. It’s a strong strategic move toward getting the interview, and that’s the whole point.

Yes, You Really Need a Cover Letter

I get it, cover letters are no fun. It’s hard to know what to say, you have to brag on yourself a little, they can sound stilted and awkward instead of flowing naturally, and they generally take up time you’d rather spend on almost anything else.

It makes sense that people want an excuse to get out of writing one. I often get asked: But do I really need a cover letter?

The short answer is yes. An emphatic yes.

The Excuses

Let’s get the excuses out of the way. Some of the most popular:

  • The application didn’t say I needed a cover letter.
  • So-and-so didn’t write a cover letter when they applied for their job and they got the position.
  • I’m not applying for a communications position, why should I write anything?
  • No one is going to read it anyway.
  • I just don’t have time for this.

There’s one simple and resounding reason you should send a cover letter with every single job application: It’s a major way to set yourself apart from the other applicants. (And that’s what you want, right?)

Set Yourself Apart

A cover letter is your chance to show a potential employer what you’ve got. Heck, even just writing one can show extra initiative over other applicants. If the application didn’t say to send a cover letter, almost everyone who applies will probably skip it. How does it make you look, then, when you’re the one who took the time to do it? Pretty dang good.

Even if other applicants are sending in cover letters, or it’s a requirement of your application, a well-written cover letter can still be your secret weapon. A cover letter that explains how your experience and interests match up with what the job is looking for will make you stand out from most other applicants. Remember when I said cover letters are hard? They’re hard for (almost) everyone. And because they’re hard, most people just churn one out. If yours shows any kind of thought and intention, believe me, you’re already ahead of the curve.

Show You Have Communication Skills

Just because you’re not applying to be a writer doesn’t mean communication isn’t important to your potential employer. Communication skills are part of almost any position in one way or another. If you can string sentences together to form a coherent thought, that’s a good sign you’ll also be able to do so speaking to teammates or when creating job-related documents and reports.

Prove You’re Not a Nightmare Employee

The cover letter shows your potential employer that you’re not any of the following: horribly self-absorbed, delusional, immature, inappropriate, or likely to light your hair on fire and run out of the office. (If you are any of those things, now is a good time to practice pretending that you aren’t.)

Story Time

Writing about yourself like a rational human being to a potential employer may sound like common sense, but bad employee traits have a tendency to show through in cover letters. I’ll give you an example:

I was on a hiring team for a position that was fairly difficult to fill (tech people may understand when I say they wanted someone who could both do excellent web design and excel at front-end coding). An application came through from a person who had the skills we needed, which is more than we’d seen from most other candidates. But, I kid you not, this person referred to themselves as a superhero in in their cover letter.

At first, I thought they were just being cute or clever and it wasn’t working. As I finished reading the letter though, it was obvious that the applicant really thought of themselves as a superhero, down to having adopted a superhero name and tagline.

I didn’t recommend the applicant for an interview — the cover had told me a lot about what it would be like to speak with them. But we ended up giving them an interview appointment anyway. When they walked in, they were everything their cover letter intimated: a superhero gone wrong. They were too arrogant and strident, and they made it clear they thought they were better than our organization. Needless to say, we didn’t give them the job. I could see from the beginning we wouldn’t just from the way they wrote their cover letter.

Maybe an extreme example, although this kind of thing has happened more in my experience than you’d think. But the point is: All skills and background being equal, if your even-keeled, thoughtful cover letter gets submitted alongside a poorly conceptualized one, your chance at the interview shoots way up.

Your Chance to Talk

Question: In the job application process, when do you get a chance to say what you are looking for? What you’re interested in and why you want to work with the company and all that stuff (I hope) you want to say? The resume is all about the potential employer and what they want. You barely get to say a thing about what you’re wanting in your next position.

Answer: The cover letter. That’s where you show your passion for your work and your interest in this particular employer. Not only do you get to say your piece, but you show your potential employer your commitment to your work, your interest in their company and why all of it would be a great fit.

Getting Started

Even if you know you need a cover letter, it’s hard to know where to begin. The great thing is, it doesn’t have to be perfect, especially at first. You can fine tune it as you go. Just keep three things in mind as you write:

1. Focus on how your skills and experience match the position.
Answer what the company is looking for with information about your background. Avoid writing a storied account of your employment history that has little to do with the position.

2. Show your enthusiasm.
Talk about the things that make you a great employee in your field: how you approach your work, what matters to you, what stand by or can’t stand in a work process. Bonus points if you can align these things about yourself with things the company does/has done or is looking for.

3. Highlight your strengths.
It is so hard to write about yourself. But stay away from talking about your weaknesses. It will only distract your potential employer from your strengths. As a general rule, don’t spend time talking about: layoffs, employment gaps, career changes, disputes with past companies, etc. If they ask in an interview, you can answer (tactfully!). If they don’t, let it lie.

Now, no more excuses! Go write your cover letter.


About Resumes Are Hard

I’m Bailey at Resumes are Hard. I'm a long-time content strategist and reviewer of job applications. I help people write resumes and cover letters that highlight their strengths and downplay their weaker areas.