How to Get the Most Out of Hiring a Freelance Writer

How often do you ask for help with your work?

For most people, and especially for entrepreneurs, asking for help carries some stigma — there’s an unfortunate stereotype that suggests we should be able to do everything ourselves, and that asking for help is a sign of weakness or failure.

But in reality, no successful person has ever achieved what they’ve achieved alone. In fact, many of the most successful people are those who ask for help readily, intelligently, and without embarrassment.

If you like, we can call it something different — outsourcing, collaboration, or smart utilization of other people’s skills.

Just as the internet offers a multiplicity of ever-more-specific niches, so too do we all have different niche skill areas as human beings. Some of us are good at planning ahead; some are good at doing magic with numbers (I envy you guys); some can spark infinite creative ideas on demand; some are great with words.

Because we all use words every day, we may expect ourselves to automatically be able to write, and either give ourselves a hard time when we’re not all that great at it or doggedly plough on in our ventures, without acknowledging that writing isn’t one of our niches of expertise.

But smart, successful businesspeople strategically maximize their own skills while making the most of others’. They know that hiring a good freelance writer — a professional wordsmith — is an investment that can free up a huge amount of time and energy, which can be used to focus on other aspects of their business.

A professional writer can help craft your vision, message, online content, or any other piece of written communication into something slick and punchy that grabs people and says what you want to say, how you want to say it — but better.

If you find yourself needing well-crafted communication, and are smart enough to be considering hiring a freelance writer, you need to know what crucial work to do in preparation to hire an expert writer and then how to get the most from the arrangement once you’re up and writing. Here are my best tips, learned the hard way in my work as a writer-for-hire, for how to get the most from this working relationship.

Know What You Want

“If you don’t stand for something, you’ll fall for anything.” — Anonymous

A writer can: respond to your vision to help you express what you want to say in clear, concise, articulate, appealing, specific, professional, and audience-tailored ways.

A writer can’t: read your mind, define your objectives, make a vision if you don’t have one, work out your business strategy, or rebrand your organization.

Writers get asked to do these “can’ts” all the time — I know I have been. However, this level of thinking is, most of the time, out of the scope of what the writer has been hired to do, and they are almost certainly being underpaid for that type of work. Plus, if you want your writer to set the strategic direction, they may lead the work in a direction you don’t really want to go.

Too often, I’ve worked with clients who know they want a writer but are otherwise completely unsure as to what they want the writer to do. And, as a writer working with a client, it’s very hard to give people what they want if they don’t know what that is.

The number one key secret to a successful relationship with a freelance writer is to clearly define what you want before entering into the relationship.

It’s a good idea to write a brief (a proposal) that covers as much information as possible: word count, tone, look and feel, keywords you might want to use, examples of your existing communications that you want to match, or external examples that you’d like to emulate. Include deadlines, length of the contract, and what deliverables you’re expecting (as far as you know — i.e., 10 blog posts, sales copy for X products, one 800-word bio).

Think about whether you want someone with extra skills, such as graphic design, SEO-optimization, WordPress formatting, or marketing skills.

Will you pay them hourly or a fixed price? What’s your budget? What are you expecting to get for that money?

The more clearly you define what you want, the more likely you are to get it — and for less time and money than will be the case if you just say, “Um, I need some kind of overall company description… maybe longish… or not… can you write something… that, like, just makes me sound really good, and makes people come to my website?” (Yes, I have had “briefs” like that).

Your writer doesn’t need your whole life story — they’re a wordsmith, not a therapist — so keep the brief brief, so the relevant information stands out clearly.

We’re writers — we craft pieces of content according to the objectives we are given. If the objectives aren’t great (or are non-existent), it’s going to be frustrating all round.

Think Strategically About Your Audience

If you’re considering outsourcing a writing job, chances are you need a piece of writing that will achieve a specific end result. Whether it’s succinctly communicating your company’s values or turning your 100-page stream-of-consciousness Google Doc into an e-book, it’s crucial that your writer knows what that end result is, and that means one thing: acknowledging the reader.

Let your writer know who your audience is or what the key market is that you’re trying to reach. This action goes hand-in-hand with defining the voice and tone for a piece (which we’ll look at next), as the ‘how’ of a piece of writing will vary based on who it needs to speak to.

Consider the different tone of voice you would naturally use in an email to your boss, an email to your mother, and an email to someone you’ve been on two good dates with. Knowing your audience is important!

If you need writing for your business, let your writer know as much information as possible about who the audience (your customer) is, what their habits are, how you interact (or want to interact) with them, and why they should care about your business and what you’re doing.

Only if they know who they’re speaking to will your writer be able to craft a piece of communication that effectively reaches that group.

Your target audience may also affect your choice of writer; most professional freelance writers will offer versatility but still inevitably have their own unique mode of expression. Choose someone whose tone of voice and personality will resonate with your audience. For example, if you’re creating a website with healthy relationship advice for teenagers, you should choose someone who will be familiar with the word use and slang of your target audience, whether they’re a younger person themselves or experienced at connecting with young audiences.

Understand Voice and Tone

One of the challenges I face as a freelance writer is explaining voice and tone to clients.

“But writing is writing, right?” they usually say.

Wrong. Writing is (ideally) a fine art that uses words in a creative but precise way to craft specific pieces of communication, all of which have a certain quality that we can describe using words like mood, personality, tone, or voice.

Just as every person you’ve ever met draws on language in various ways to express themselves (think of the regional differences between using soda, pop, soft drink, or coke), so too does every piece of writing use words differently to create an overall ‘feel.’

The feel is the most powerful part of the art of communication, and it’s important to know of what kind of feel you want so you can ask for (and therefore get) what you need.

In our rational, fact-oriented societies, we tend to think that the key aspect of communication is what a piece of content is saying. However, as every advertiser, marketer, salesperson, artist, novelist, and emotionally intelligent person knows, the most important thing is not what is said, but who is saying it (voice) and how it is said (tone).

Together, these qualities make up the essential character — the feel — of a piece of writing.

Tone comes from a complex, often intuitive combination of word choice, word length, sentence structure, paragraph length, use of references, pronoun use, and much, much more. Like a piece of music, you can pull it apart piece by piece and still never really understand the magic of the whole.

The whole art of writing involves drawing on the toolkit of language to combine content, voice, and tone into a seamless piece of communication. For example, consider the difference between these two introductions to a website:

Welcome. As the leading authority in uniform solutions, WEAR clothing creates professional workwear that is fair, affordable, practical, and beautiful.

Or…

Hey! Welcome to WEAR clothing, the hottest new thing on the block when it comes to practical uniform solutions. We would LOVE to help you outfit your crew in comfy, stylish, and most importantly, ethically made threads. Read on!

Very different tone and voice — two very different companies are implied.

If you let your writer know what tone of voice you want for your project, you are far more likely to have a result you’re pleased with, and as a bonus, you’ll have an efficient and happy freelancer.

To capture the appropriate tone, you might like to imagine who the implied speaker of your piece is. Is it you? Your brand? A neutral third party? What are some words that might describe the personality of the speaker: are they chatty and excited about what they’re saying, or are they a sober, research-driven academic? Describe them as you would a person — get creative.

One approach to helping your writer nail the right voice and tone for your piece is to supply samples of writing or copy that you feel speaks in the right voice and that you would like to emulate.

A good writer can help you work out the best voice to speak in, but just note that this kind of thinking is strategy rather than just pure copywriting — it may cost you extra, or it may be beyond the skills of the wordsmith you’re working with. If you’re really unsure about your business’ voice/values/identity, you need to figure those things out first; consider hiring a marketing consultant or working with a branding specialist before you hire a writer.

It’s so crucial to get the right tone and voice, because they are what will help you speak to the right people and connect with your all-important target audience.

But how do you find a writer who can nail your project’s voice and tone, you may ask. Well, you can…

Ask for a Sample

Now that you know what you need from a writer, you can start looking for your perfect match.

In order to find a good writer, it’s pretty standard practice to ask for a short writing sample, especially if you’re forging an ongoing relationship. This sample can either be of previous work, or if you’re looking for more of an ongoing relationship or are working on a bigger project, you could ask for samples written specifically as part of their application.

What’s not ok is asking for a custom-written sample as a sneaky way to get free work. Please don’t do this. It makes writers sad and cross (and hungry).

If you ask potential hires to write you a sample, it should never be more than 500 words. You should also clearly articulate what you’re looking for, so a writer can know before they put the effort into a sample whether they can meet your needs or not.

If you end up with several good samples to choose from, look for the writer who most closely meets the requirements you set out in terms of voice, style, specific things to include, and clear progression of ideas.

Or if you’re reading examples of existing work, look for high-quality work that shows great command of language (interesting but not pretentious word use, doesn’t use “nice” or “very” every second sentence, avoids repetition, and doesn’t make long, waffly sentences), flexibility of tone across several projects for different clients, skills using research and referencing, and the ability to craft creative and snappy phrases that make you want to keep reading.

Notice your feelings while you read their sample; the best writers can make anything interesting, so if you’re bored and tuning out, keep looking.

Respect Their Work

To get the most out of working with a freelance writer, I recommend that you work with the writer during the editing process. Don’t edit a writer’s work without their input. All humans use words, as mentioned above, and so it’s tempting for any business owner or client to think they know best, rendering ineffective the service they’ve just paid for.

Google Docs can be a good place to work collaboratively, as you will have one master document and you can comment on and suggest changes to the text without irrevocably altering it. You can also have conversations in the comments to better explain why something isn’t working or understand why a writer did something a particular way.

If you’re unhappy with the end result, ask the writer to rework the piece to your specifications, being as clear as possible (don’t avoid being honest in order to try and save their feelings: they’re a professional). And don’t freak out too soon: often a few rounds of back-and-forth discussion are a healthy part of the process.

A first draft can be a great tool for you to discover what you don’t want. A good creative process is rarely linear: use perceived ‘failures’ to refine your awareness of what final result you’re really wanting.

If you’ve contracted a piece of work —a series of blogs, for example — to a freelance writer and you really don’t like what comes back, take a moment for self-reflection before yielding to despair or cursing the writer and looking for a new one.

Did you clearly define what you wanted? Did you give examples of the tone of voice you wanted the piece written in? Did you ask for a sample or review examples of the writer’s other work? Did you clearly explain who the piece of writing should speak to and what important information it should include?

If the answer to all of these is yes, and you still feel the results are wildly off-key, take the time to explain your issues to the writer and give them a chance to address them.

If it remains obvious that you’re not singing from the same songbook, then it might be time to look for someone else who you click with better or who is more suited to your needs.

Once you find a writer you like and respect, and who ‘gets’ what you’re doing, it’s time to…

Build a Relationship

Like with anything in life, whether personal or professional, the quality of a human relationship is the key difference between a productive, happy, positive experience and a dreadful, negative, waste of time.

When you’re looking for a freelance writer, it’s a good idea to interview potential candidates so you can find someone who you ‘click’ with: someone you get along with at a personality level and can build a good level of unspoken understanding with.

If you find a writer you can build a solid, happy relationship with, over time they will learn to intuit your needs and that of your projects, making both of you more able to churn out good work. The ultimate goal is someone who ‘gets’ you and can effortlessly anticipate your requirements —  but that takes time.

And just like with any good relationship, when you find them, do the work to hold onto them! So much of the work in freelance writing is the initial effort where clients and writers get to know each other and discuss their goals and needs, so if you can build an ongoing relationship, it will be more efficient all around.

How do you hold onto a good writer?

• Pay them fairly and on time.
• Be clear in your requirements.
• Don’t hit them up with unreasonable panicked deadlines if you can possibly help it.
• Remember your anniversary (oops, wrong kind of relationship!).
• Let them know you appreciate their work.
• Publicly acknowledge them where practical and appropriate.
• Don’t ever send them 20 emails in one day, all in caps. (Yes, this happened to me. No, I don’t work with that client anymore.)
• Recognize the issues that aren’t their fault, and don’t take out your frustrations on them.
• Pass on positive feedback when it comes in.

A great relationship with your writer is the secret to effective, no-fuss, perfectly accurate writing. The better the relationship, the more trust you have, and the more you’ll feel comfortable handing the reins over to your trusty writer and getting on with what you’re best at.

Whose Is It?

Finally, make sure you’re clear on who owns the writing that is produced. The legalities will vary from country to country, but you may wish to create a contract that clearly defines ownership for any content you produce together.

The time to make any legalities clear is before you start, not mid-way through or six months (or six years) later.

Whether it’s an informal agreement or a formal contract, make it clear who will own the rights to whatever content is produced. Are you ok with the writer using it as part of their portfolio? Do you need a confidentiality agreement? Do you need a copyright licence?

Define ownership at the same time you work out pay rate and scheduling — that way you’ll prevent misunderstandings further down the line.

You Can’t Do It All Yourself!

So if slick wordcraft isn’t really your buzz, do the smart thing and ask for help: use a professional writer to say the things you need to say in the best possible way.

Asking for help isn’t weakness: it’s an intelligent investment that allows the best person for the job to use their expertise and do what they do best. It’s good leadership — putting aside the need to prove anything, and instead matching the right task with the right skillset, in order to allow yourself to focus on what you do best.

Do the right preparation so that you can clearly articulate what you need, and take the time to look for a writer that fits with your audience and your voice.

Find someone you actually like, who understands what you’re about, treat them well, make your needs and expectations clear, and you’re on your way to a sweet and fruitful relationship. May you produce lots of happy pieces of content together!

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