Write This Way: How to Improve Your Chances of Landing Your Next Job

Good thing you’re a creative pro. Because whether you want to win over a new freelancing client or full-time employer, a job search is fundamentally a creative challenge.

However, when it comes time to land a new project or position, many creative pros make mistakes that damage their chances of getting hired. So here’s some friendly advice that can improve your likelihood of getting the work you want.

Before you begin: arm yourself with an organized approach.

Save yourself time, effort, and anxiety by setting up a good system for keeping track of everyone you plan to contact. Though you may love using an old-fashioned paper-and-pen approach, I strongly recommend that you go digital. That way, you’ll be able to find records quickly, avoid duplicating your efforts, and easily categorize everyone you contact.

Organization is a beautiful thing. Setting up a system to capture all your job-search information will eliminate chaos and save your sanity.

A spreadsheet can work pretty well (Excel, Numbers, Google Sheets, etc.). You can set up columns with titles like: First Name, Last Name, Title, Company, City, State, Website, Email Address, Phone Number, Notes About Company, Notes About Contact Attempts. If you like, you can color-code cells to highlight your hottest leads or coldest dead ends.

But better than a spreadsheet, I think, is a CRM software solution. Technically, “CRM” stands for “customer relationship management,” but you can pretend that “C” stands for “client” or “contact” or “coworker-to-be” and use the system to keep track of everyone you’re pitching.

There are countless CRMs for sale out there, but I’ve been using HubSpot Free for several years and I love it. It makes it easy to record all the important information about the companies and people you’re trying to pitch yourself to.

You could, for example, categorize each of your target companies, if you wanted to: design studio, ad agency, in-house creative department, printer, etc. Just ask yourself what details will be helpful to you in the future and capture them as you go along. (HubSpot even enables you to keep emails between you and your targets, if you like.)

Start by sleuthing.

There are several reasons you should research the heck out of the companies you pitch:

To determine whether or not you actually want to work with them. For example, if I’d known that the company I was interviewing with many years ago boasted an on-site employee hot tub (ewww), I never would have bothered going in for an interview.
To track down the names, titles, and contact information of the people you should contact. When you’re a creative pro, it’s almost never the HR department you want; it’s a creative director, chief creative officer, or even the owner of the company. You want to hunt down the people who can judge your portfolio.
To arm yourself with knowledge. If you do decide to pitch a particular company, you’ll need to demonstrate that you understand and appreciate their work and explain how you can help them.

Find out: What kinds of clients does this company serve? What type of work do they create? How long have they been in business? Are they independent, or are they beholden to corporate overlords and shareholders? Talk to your network and look for articles, reviews, podcasts, and subreddits. You might learn about impressive accomplishments and awards; you might discover charges of sexual harassment and tax evasion.

Channel your inner Sherlock.

Finding a decision maker’s email address can be tricky. Here are some tried-and-true methods:

Call the company’s main number. If someone actually answers, confidently say, “Hi, my name is ___________, and I need to send my portfolio to ___________. Can you please give me their email address?”
Ask your friends and contacts. As a bonus, they might be able to share information about the company and its employees.
DM your target on social media and say, “I’d love to send you my portfolio. Could I please have your email address?”
Find your target’s profile on LinkedIn and click “contact info.”
If you know anyone else’s email address at the company, apply the same format to the name of the person you’re trying to reach.
Type the person’s name and the word “email” into the Google machine.
Look for articles written by or about the person you’re trying to reach. Sometimes you’ll find a contact link at the end.
Go to Listen Notes and type your target’s name into the search bar. You’ll find every podcast they’ve appeared on or been mentioned on. Contact information will often be provided in the show notes and/or at the end of a podcast. Bonus: Podcasts are a great way to get to learn more about people.
If all else fails, take a guess. A larger corporation will likely have this standardized email formula: [email protected].

Think like a copywriter.

Effective copywriting requires putting yourself in the proverbial shoes of the person you’re speaking to. That can be challenging when you’re writing an ad that will be read by thousands of people. But lucky you—during your job search, you’ll be able to focus on each individual you’re addressing.

Say hello to Sam.

So that I don’t have to keep referring to the person you’re trying to win over as “your target,” I’m going to give that person a name. I’ll go with “Sam,” which can conveniently work for any gender.

Get inside Sam’s head.

Whether this person is a creative director or chief creative officer, you can assume a few things about Sam and craft your writing accordingly:

Sam is busy, with deadlines to meet, a team to manage, and clients to keep happy. Keep your writing pithy and easy to scan, and make the link to your portfolio and contact information a cinch to find.
Sam needs someone dependable. Some job-seekers like to fudge their resumes or overstate their experience. But that—to use a mangled metaphor—can get you into the kind of hot water that burns bridges. If you tell Sam you’re a Photoshop wiz or a printing pro, you’d better be. Sam doesn’t have time to fix your mistakes, and if you dupe Sam, your reputation will suffer.
Sam appreciates working with pleasant people. You don’t need to act obsequious, but you should be respectful and polite. Let a little humor shine through, if that comes naturally. Express your eagerness (“I’d love to join your team”), but not your desperation (“I really need to pay off my hospital bills”).

Show Sam that you care.

Demonstrate that you know Sam’s company well. You don’t need to list every fact you’ve managed to dig up, but try to customize your writing using pertinent information. You might say something like, “I wanted to introduce myself because I know you have a lot of clients in the adventure-sports space. I’m a competitive paraglider, spelunker, and bog snorkeler, so I’d love to get to work with you.”

“Me” and “you”: Strike a balance.

You want to come off as capable and confident, not as an insufferable prima donna.

When you’re pitching yourself, you might be tempted to only talk about…yourself. But if you’ve ever been in a conversation with a bloviating blowhard who only drones on about their own experiences and capabilities, you know what a turnoff that can be.

Instead of harping exclusively on how wonderful you are, try to move some of your focus over to Sam and the relationship you’re proposing between the two of you. Consider beginning your email by paying Sam a sincere compliment, if one is deserved. Something like, “I saw your toilet paper campaign in the Adtastic Awards catalog and loved it. The billboard with the cockroach was my favorite.”

Take note of how many times you refer to yourself vs. how many times you refer to Sam and Sam’s company. I can’t give you an exact ratio to shoot for, but do ask yourself if you’re tipping into narcissism territory.

Describe how you can help.

Reflect on your skills and strengths and explain what you have to offer. If you’re great at coming up with big concepts, say so. If you love illustration or lettering or logo design, share that. Maybe you’re a down-and-dirty production workhorse. Let Sam know—everyone needs one of those at some point.

For example, you might say something like this: “I see that you have a lot of CPG clients. I adore working on packaging—in fact, my senior project in art school was coming up with a completely new take on Girl Scout Cookies. You can see that work here” (embed a link).

A few more writing tips.

Embrace simplicity. When in doubt, make your sentences shorter, rather than longer. No one will complain.

Kill redundancy ~~dead~~. Eliminate every unnecessary word. This is a subjective endeavor. But as you read over what you’ve written, continually ask yourself, “Do I need this word?” And if the answer is “no,” kiss that word goodbye.

Opt for active. The passive voice is not wrong, but only use it if you must. It’s generally a circuitous way to make a point, which is why shifty people say, “Mistakes were made” instead of “I screwed up.”

Approach clichés with caution. I’m not going to tell you to never use clichés (e.g., a fish out of water or smart as a whip), but when you do, ask yourself, “Could I make this better? Less hackneyed? More truthful, informative, or interesting?”

Include a call to action. Nudge Sam in the direction of responding to you. For example: “Even if you have all the help you need right now, could you please take a gander at my portfolio and let me know what you think? Just three adjectives would make me happy.” Or, “If you could spare a few minutes to tell me about what kind of design help you’re seeking, I’d love to talk. Do you have any time this week?”

Remember: Typos kill.

Do you think that sounds hyperbolic? It isn’t. The fastest way to murder your chances of getting hired is to look careless in your email, your resume, or your website. If you can’t bother to check these things, Sam figures, you won’t bother making sure your work is watertight.

A few proofreading tips:

Pay attention to spellcheck and grammar-check and/or use Grammarly. They’re not always right, but don’t dismiss their suggestions without good reason.
Use the “find” feature to make sure every opening quotation mark has a corresponding closing quotation mark. Same goes for parentheses.
Go for consistency. If you start one bullet with a capital letter, make sure you do the same for all your bullets. If one subhead uses title case, make sure they all do.
Stay parallel. See how all of these bullets in this list begin with the imperative mood, like a command (Pay, Use, Go, Stay, etc.)? That means they’re all “parallel” with one another, which makes them easier to read.
Make sure all smart quotes and apostrophes are curving in the correct direction. More on that here.
Do a search for double spaces. No one needs them.
Double- and triple-check the spelling of company names. Your spellcheck will probably overlook capitalized words.
Read your email out loud—slowly. It will help you catch errors and assess how your writing sounds.
Proofread with fresh eyes. After checking your writing, walk away for a while. Then look it over again.
If you know you’re hopelessly error-prone, consider hiring a proofreader.

Say no to these no-nos.

“Dear Sir/Madam.” This basically announces, “I can’t bother finding out who you are.” Also, it’s antiquated and stuffy and awful. Don’t touch it.
Flagrant copying and pasting. If you must copy and paste, do so with the care of a bomb technician. An obvious copy-and-paste job says, “You’re just one of a million people I’m trying to get work from” and also, “I’m sloppy.”
Bad design. Surely you know this, but not everyone seems to. Your resume, website, and any other self-promotional pieces have to be EXCELLENT. Your first impression can open the door to opportunity or slam it and lock it.
Misspelling the name of your target. It’s an instant insult.

What about snail mail?

Considering the dozens or hundreds of emails we receive every day, a tangible, three-dimensional piece can really stand out from the clutter. It also gives you a great opportunity to show off your creativity and design skills. And in theory, you can come up with a design so nifty, or a gift so useful, that your name/brand will end up living near Sam, keeping you top of mind.

The downside, of course, is the cost. An email costs you nothing, but mailings and swag can get pricey.

Gauge the interest of the people you contact, and if someone seems like a good lead for future work, consider putting them on a list for a snail-mailing. There’s no limit to the types of engaging mailers you can create. Consider sending:

A handwritten note on a good-looking postcard you’ve designed.
A creative mailer. Think about translucent envelopes, unconventional dimensions, sumptuous substrates, and creative folding and die-cuts. (Just be sure you use sufficient postage.)
A recipe, a joke, a time-saving tip, a fun fact…anything you believe Sam would appreciate.

Have fun!

I say this sincerely: Enjoy your new-business or job search. Think of it like a challenging fishing excursion. You’re not going to snag every fish, but by exercising patience and constantly observing and tweaking your technique, you will eventually feel a tug on your line and get the opportunity to reel in the work you want.