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What I Learned Reviewing 212 Freelance Writing Pitches

We publish a lot of (excellent) advice from writers on Horkey HandBook. But this guest post from Laura Pennington reveals the ingredients for a good pitch from the hiring manager’s perspective.

Recently, Laura was in charge of hiring a team of freelance writers for a client’s project. We asked her to share what the rejected pitches had in common, and she happily (and honestly) obliged.

Here are Laura’s tips on how to make sure your pitch gets accepted.

Over the course of my own freelance writing and project management career, I’ve reviewed a lot of freelance pitches for others. I used to work for a client handling a team of 20 writers and I also managed digital teams for Upwork, TrueCar, and Microsoft.

One thing I’ve learned is that many people are making critical errors early on in the application process with their freelance writing pitch.

One of the most frustrating things about pitching is that when you get no response to your freelance writing pitch, you’re not sure why. Am I right? I’m here to give you my perspective as a hiring manager about what’s potentially going wrong.

What’s sad about this is that so many people are getting rejected before even getting a chance … and they don’t know why. So let me give you some insight.

I recently had the opportunity to serve as a project and hiring manager for a company hiring SEO writers for business topics (maybe you even applied because you saw the posting in an email from Horkey HandBook!)

In the course of that project, I received and reviewed 212 freelance writing pitches.

If a writer passed my initial review, they were then sent on to a team of editors and given a test project. This particular client had a specific way of doing things and writing requirements, so it was important to screen in advance.

What I learned from managing this writing project is that a lot of freelance writers are doing themselves a disservice in the application or follow-up process. These might seem like minor issues, but with a lot of freelancers to choose from, it means you end up getting cut early on and never get a chance to advance to the next level with the client.

While some of the applications I received were excellent, others fell very short. And I noticed that those falling short all had the same mistakes.

Pitching and getting clients interested is the bread and butter of your business. You can’t easily grow a portfolio, land retainers, scale your business, or pay your bills if you can’t convince clients you’re amazing in the pitch.

In a second piece of this two-part series, I’ll explain mistakes that often happen once you’ve been hired that cost you regular clients. But in this blog post, let’s focus on pitching only.

Not sure what niches you can specialize in as a freelance writer? We’ve done some research and brainstorming for you, and we came up with over 200 niches to choose from. Here’s the list:

Here’s the simple truth: You have to get your foot in the door. You can’t do that unless your pitch rocks.

Let’s walk through the most common mistakes I saw with pitches. These often led to people being eliminated after my review, so most people never even made it to the editor’s review. Taking a look at your pitching approach and your writing samples based on these tips will help you put your best foot forward and land more business with a stellar freelance writing pitch.

Freelance Writing Pitch Mistake #1: Spelling and Grammar Errors

The number of people who have spelling and grammar issues in their writing samples or their pitch email always surprises me. In this project, out of 212 applicants, 88 had spelling or grammar mistakes within their writing samples or pitch email.

What I Learned Reviewing 212 Freelance Writing PitchesThis is a huge no-no. When I review pitches like this, it’s my first line of defense to weed the candidate pool down.

Your pitch and writing samples should be perfect. They should reflect your best work.

They should make the client say “Wow! We NEED to hire this person.”

Hire an editor. Ask a friend. Never submit sample work to a client that is not the tightest and best you have to show. If you’re sloppy here, the client is not interested.

Staying committed to editing your work will make you a better writer and it will impress more clients. Many writing samples were just not up to par because they appeared to have been written hurriedly. Invest the time. It will pay off.

Freelance Writing Pitch Mistake #2: Irrelevant Writing Samples

I’m not going to name names, but several people submitted samples that were so off base with what the client was looking for that I couldn’t honestly tell if they’d be the right fit. This particular client needed SEO articles for a very professional/educational B2C website, so the guy who sent me his very personal blog about his divorce? He didn’t make the cut.

You don’t need to go out and create writing samples for every individual client. In fact, don’t do that.

However, you should have some writing samples related to the clients you intend to pitch. If you’re pitching a Buzzfeed-style site, have something humorous. A corporate client? Have a whitepaper ready. An SEO blog? Make sure you’ve got SEO samples.

Here’s a pro tip: The writing style is ten times more important than where you’ve published the piece. I don’t care if your piece is on Entrepreneur or Business Insider if it’s not chock-full of excellent writing.

I’d rather see a Google document with a piece that’s never been published anywhere but has excellent style and flow. I think so many writers get hung up on “I’ve never been published anywhere.” Most clients don’t care. Talent is more important.

My first three writing samples landed me more than $30k in business my first year and they were never published anywhere.

Freelance Writing Pitch Mistake #3: Sending Way Too Much Information

Keep it short and sweet. Blow the client away with your ability to be concise and clear. I’m not going to review five writing samples. I’m probably going to look at the first one and see if you’re a fit. If I’m interested, I’ll read more.

The takeaway from that? Don’t put your best sample at the bottom. Add your best sample first.

Also, make it easy for the client to open (Please, nothing they have to download! Dropbox and Google drive are your friend.)

If your freelance writing pitch is six paragraphs long, the client will not read it.

If you attached 20 writing samples, the client will not read that either.

Give them just enough to pique their interest so they reply to you to learn more. Don’t overload someone who could be looking at dozens or hundreds of samples.

Freelance Writing Pitch Mistake #4: Poor Follow-Up

The instructions for the job indicated that due to the volume received, a response would not be provided to everyone.

Trust me, when I received pitches with poor writing samples, I wanted to write back and give some helpful advice. But at the end of the day, the client was not paying me to help improve pitches. They were paying me to find the top writers.

That meant you had to impress me with your freelance writing pitch alone.

However, some people did engage in very professional follow-up, circling back a day or week later to ensure things were received.

Some people, though, did some really unprofessional things in their follow-up. That meant that even if they had been on my shortlist, they were removed.

Clients do not want to work with difficult freelancers. Ever.

I don’t care if you’re the best writer in the world. Clients have a choice and many would prefer someone easygoing and not rude.

Here are some examples of real emails and one voicemail I received as the project manager. If you sent this, you came across the wrong way and were not given a chance. Think about your choice of words because things can easily be misinterpreted.

“I’ve been waiting for a week and heard nothing. Are you even reading your emails?”

“Hellooooo….. I guess you hated my work?”

“Hi, this is ______. I found your number online. I applied for that freelance writing job but didn’t hear anything. I guess you hated my work. Anyways, I wanted to let you know I don’t need you anymore. I’ve accepted a full-time job. Bye.” (This was a follow-up phone call to the response above. I would not ever consider working with this person again because their follow-up was so unprofessional.)

“Hey, here are some more writing samples in case you want to see more.” (Note: your best work should always be sent first. Don’t keep it a secret. The client will ask if they want to see more.)

What Freelance Writing Pitches Stood Out?

Overall, my team hired 15 writers. Several things helped those people stand out in the pitching process that ultimately got them to the next level and finally hired. (As a side note, several Horkey HandBook applicants were top notch in this area and received an immediate approval from the client.)

Here’s what helped people crack open the door with their freelance writing pitch:

· Writing samples in the same field as the client;
· Pitches that contained 1-3 really stellar related writing samples (as opposed to 10 or 20, which no one has time to read);
· Video pitches that showed some personality;
· Examples of specific client feedback.

The bottom line is that pitching is an art form.

It takes time to master it, but please keep in mind that you need to be clear, concise, and professional.

Your writing samples should prompt the client to get back in touch with you right away. Put yourself in the emotional shoes of your client: What would YOU want to see if you were hiring writers?

What feedback can you incorporate to make your pitches stand out from the crowd when you next submit to an online writing gig?

Laura Pennington launched her freelance writing and project management career in 2012 after burning out as an inner city teacher. She scaled her business to six figures in less than 18 months and now hosts the Better Biz Academy podcast with advice for freelancers on landing ideal clients, marketing, and work/life balance. She can be found at www.betterbizacademy.com

Gina Horkey

Gina Horkey


Gina Horkey is a married, millennial mama from Minnesota. Additionally, she’s the founder of Horkey HandBook and loves helping others find or become a kickass virtual assistant. Gina’s background includes making a living as a professional writer, an online business marketing consultant and a decade of experience in the financial services industry.

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