Content Creation

7 Questions Marketers Should Be Asking When Hiring Freelancers

By Molly Conicella on August 9, 2018

As a seasoned marketer, you understand the value of creating high-quality content that people can connect with based on their wide range of interests and needs. In order to fully develop a diverse and full-bodied content canon that captures the hearts and minds of people, you will likely find yourself needing to bring on a staff of writers and freelance creators to keep up. While the internet is rife with freelance talent looking for work, marketers are spending more time vetting and selecting the right content creators.

Marketers in need of freelancers must consider a number of criteria from industry experience, to social reach, to tone, and adaptability when evaluating what type of writer best suits their brand's needs.

As Skyword's community manager, I spend most of my days attempting to pair up brands with written and visual content creators who can best represent the voice of their brand and communicate a strategically resonant message to their target readership. With such a large pool of potentials, it can be overwhelming. Yet, over time, I've come to understand what particular questions I need to prioritize when determining whether or not a freelancer will be able to mold their writing to a particular client's strategy and purpose.

Here are seven smart questions to ask yourself when evaluating potential candidates to narrow down a large pool of writers to those creators who will be able to advocate for your brand's content.

1. Do You Need Real-Life Practitioners?

Writers who have both real-life industry expertise and a strong writing background are some of the strongest resources for clients when it comes to valuable content creation and offering readers the most value. These are the writers who have the ability to share authoritative industry ideas and tell a great story at the same time. For example, an animal product company may be looking for practicing veterinarians to contribute health-related articles to their content hub. Practitioners elevate the content to meet the needs of the trickiest audience member and ensure the content isn't elementary. Having someone well-versed in the subject matter will mean that their voice and knowledge is authentic. If you were to give the same high-level topic to someone without industry expertise, they would have to work entirely off of research and come away with mainly generalized, basic takeaways that your educated audience will see right through.

However, understand that not all practitioners are expert writers. Are you willing to coach subject-matter experts into becoming content creators? If you have the time to mold them into the writer you need, your work with them will give you a massive return on investment. This is why we recommend looking for a seasoned freelancer who exclusively covers on one particular subject-the very same topic you hope to stand out in. These professionals will be up-to-date with industry research, news, and trends and will be able to deliver strong work that matches your brand standards.

2. Do They Have a Well-Established Portfolio of Published Work?

Once you've identified whether you're searching for practitioners or seasoned writers, the first place you'll want to look is for a portfolio of previously written content. Without writing samples, it's hard to know how a candidate's expertise will turn out in an article. In the portfolio, you'll want to find a wide range of publications, as well as recently published work. It's also a smart idea to look outside of a public portfolio for their writing. Do they publish articles on LinkedIn, Medium, or a personal blog? These outlets will help you understand what their raw, unedited work looks like in comparison to the content published at other brands and media outlets that may have been shaped by specific editorial guidelines.

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Image attribution: Nick Adams

3. How Much Industry-Specific Content Is In Their Portfolio?

Do they have several content samples that support their expertise in the space rather than just one?

If a writer positions themselves as experienced in speaking towards a certain demographic, they should have several content samples that support their expertise in the space. One stellar piece for the New York Times, Vogue, or TechTarget is a great start, but an expert it does not make. Experienced, reliable, and professional writers will have a plethora of work to support their knowledge in a specific space.

4. How Recent and Relevant Are the Samples?

Now that you've found the samples showing how they share their expertise, it's time to scrutinize each sample a bit. What was cutting edge in 1999 is not the same as what's happening today-especially in breaking industries such as technology, medicine, energy, and the like. Are their ideas current and relatable? To ensure a writer has the capacity to speak to the latest in your industry, and better yet, is able to produce thought leadership, recency of samples should be near the top of your list of things to look for. A standard best practice is to look for content created within the last two years. However, if you find older work, specifically longer form content such as white papers or case studies, take the time to review them to see how they speak to more in-depth industry issues.

5. How Active Are They On Social Media?

Not every brand is looking for an influencer, but for brands seeking a large social media presence, influencers definitely offer advantages to getting more people to engage with your content. If this is important to you, first identify what type of influencer you're searching for. Is it someone with a massive social media following? Or, would a smaller-scale influencer with followers mostly in a particular niche work for your needs?

Also, consider how much engagement each of their posts receives. Sure, they may have 10,000 followers, but if none of their recent posts have any likes, shares, or comments, the people in their network aren't very receptive to them or interested in what they're sharing. Social followings and engagement matter, and so do the platforms that resonate with your target audience. If you know LinkedIn is the network that attracts your audience, but the candidate has a huge following on Instagram, their popularity on that network will do nothing to further your campaign needs.

Beyond the numbers, take a look at what kind of content are they putting out there. Do their opinions align with your brand values? Social networks are known for being a place to share private and professional updates. However, with today's dicey political climate, consider whether you're okay with hiring freelancers that openly post about their political opinion.

social media

Image attribution: Erik Lucatero

6. What Does Their Communication Style Predict for the Future?

Once you've identified a talented pool of potential contributors, it's time to reach out to see if they'd personally be a good fit for the brand. While a portfolio and social media channels are a great place to start, there's so much more you can learn from how a candidate interacts directly with you. Their communication style is a glimpse into how they'll be like to work with in the long-term.

For example, it's a red flag when a writer takes several days to respond to an email. Of course, freelancers work around their own schedules and everyone is busy, but if they're not making a potential lead of theirs a priority, how will they treat their actual clients?

Similarly, keep an eye out for candidates who regularly introduce typos into email communications. Yes, they may be relying on their phone in the hopes of getting back to you quickly, but their first communications with you should be their best. Sloppy grammar and spelling are indicative of the need for more editing on your behalf down the road. You don't want to waste countless editing hours cleaning up basic grammar and spelling, do you?

As an extension of your brand, writers should be communicating with professionalism and within a reasonable amount of time. If not, there's cause for concern that those issues could spill into the content you're hoping to create with poor quality and missed deadlines.

7. How is Their Verbal Delivery?

At this point, you corresponded with your candidate pool and were likely were able to remove a few writers from your list due to poor follow up, bad grammar, or a simple lack of enthusiasm. Though, you still need to narrow down the list of candidates slightly before offering any of them work. Now's the time to hop on a quick call to see how well they present themselves, and also if you think they personally mesh with the brand overall.

For example, here are some questions to consider during your conversation. Can they prepare and deliver over the phone? The ability to handle interviews and converse with people well is essential, especially if you plan on introducing the writer to other colleagues and industry subject matter experts. Do they come prepared and seem as knowledgeable as they appeared on paper? Are they asking the right follow up questions? Are they doing all of the talking? All of this is important in terms of forging strong, ongoing relationships and translating the ideas from your conversation into an industry-leading piece.

Finally, ask yourself whether you liked talking with them. You're not looking for a friend, but you are looking for someone who is going to be amiable, and pleasant to communicate with when delivering assignments and edit requests.

There's a lot that goes knowing how to hire freelance writers. Though, when you work yourself through these questions, you'll be better prepared to know exactly who and what you're looking for, making the job of hiring and onboarding that much easier.

Are you actively recruiting freelance talent to power your enterprise branded content efforts? Click here to reach out to Skyword and learn how we can help you find, vet, and mange influencers, writers, designers, photographers, and videographers around the world.

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Featured image attribution: Dylan Gillis


Molly Conicella

As Community Manager at Skyword, Molly is responsible for building and evaluating diverse talent pools of influential freelance writers to meet Skyword's clients' content needs. Before joining Skyword, Molly worked in the field of clinical psychology as a Caseworker and an Intensive Care Coordinator for children with mental health disabilities. She is passionate about social change and building positive communities. Molly has an insatiable curiosity and loves to learn, which allows her to delve into any project with enthusiasm. Her current work at Skyword enables her to merge her love of building positive communities with the strategy and engagement that the Community Management team requires. Reach out to Molly on Twitter at @mollayb.