Hiring Freelancers: The Smart Guide For Small Businesses

The landscape of work is changing radically. As a business, you’re constantly looking for ways to become more agile, cost-efficient and effective. And when it comes to hiring, few things have changed so dramatically. Traditional, salaried roles are quickly making way for a new breed of professional – freelancers.

These self-employed contractors are attractive for any business looking to cut down costs and liabilities. But when it comes to picking the right freelancer, many businesses struggle or worse; hire a bad apple. As a self-proclaimed ‘good apple’ freelancer – I’ve written the following guide to make sure you find yourself a freelancer who’ll tick all the boxes and continually benefit your business.

Step 1 – Look in The Right Places

Where you search will have a big impact on the quality of freelancer you end up working with. Now, it’s tempting to use the largest, most dominant platforms – Freelancer and Upwork spring to mind. My advice – avoid these. They’re oversaturated with low-quality freelancers. To boot, the likes of Upwork are – in my experience – very difficult to work with. Poor customer service, an unstable, clunky platform and a hefty 20% commission fee are some of the main sticking points – for both freelancers and clients.

Instead, you can…

• Search locally – simply do some keyword searches for local freelancers (e.g. “freelance UI designer London”) via Google or LinkedIn – or check your loyal Craiglist/Gumtree/job board. Pick freelancers based on testimonials and work samples. Consider a meeting in-person – a rare benefit in the world of freelancing.
• Browse niche-centric platforms – These tend to offer higher-quality freelancers. Even better – paid platforms. The cost is often worth it for filtering candidates. To hire a developer, Authentic Jobs and Gun.io are a good choice. For designers, Toptal, Dribbble or 99Designs. For writers/translators, Guru, Scripted and TranslatorsTown are worth taking a look at. For all other niches, Guru and PeoplePerHour offer a wide range of options.



• Explore alternative options – Great freelancers dwell in obscure places. Reddit’s /r/forhire is a fantastic resource to match businesses with freelancers. Explore Facebook and LinkedIn niche groups. Shout out on Twitter (e.g. “ ‘x company’ is now #hiring a freelance developer! #Python #SQL #Java essential”). See work you like? (e.g. another business’s website) – ask them who did the work!

Note: If your approach is passive (e.g. listing a job on a board or platform) and you can’t choose who contacts you, make sure your job listing is as specific and descriptive as possible. You want to make sure only the most qualified, suitable prospects get in touch. Add a screening word to filter the spammers (e.g. add “write ‘giraffe’ at the beginning of your application so we know you’ve read this description”). This template is fairly good – but will need to be changed a bit to fit the freelance position.

Step 2 – Pick The Good Eggs

Picking freelancers is infamously difficult. In many cases a project has failed or gone over budget due to poor communication, disappearing contractors, or downright shoddy work. Before you contact anyone, you want to make sure they tick all the boxes. But what if you don’t know which boxes they need to tick? Here are a few things to look out for. Each candidate should have…

• Client Feedback - Numerous positive client testimonials.
• Work Samples - Work samples and previous experience on par with your required work.
• Experience - A specialisation/niche is in-line with the work you require.
• Prices - Rates roughly within your budget (try to avoid dirt-cheap freelancers – work quality is usually comparable).
• Profile - Profile description/communication is accurate, professional and in-line with your business’s goals and vision.
• Logistics - Make sure the availability, location and language are in-line with your business’s needs.
• Presence - (Optional) A prominent social media and web presence (website, guest posts).

Do they match these criteria? Great! Create a shortlist of your candidates – say 4 or 5 of the most qualified freelancers. It’s time for the next step.

Step 3 – Narrow Down Your List

Choosing your candidate will depend on how closely each freelancer matches the above bullet points. But it can also depend on how strong a connection you make – an important point to consider if you’ll be working with this person for weeks, months or even years. For this reason, I’d recommend conducting a Skype interview – voice or video.

In these interviews, cover…

• A brief background on your company (and/or your client’s) history, culture, philosophy.
• A background on your prospect’s skills, experience, and previous projects closest to your own.
• The scope and nature of your project – and whether your prospective freelancer can follow through on the specific deliverables you require.
• Logistics – including availability, required deadlines, and your budget.

Here’s a list of useful questions to ask freelance candidates. After your call, you’ll probably have an intuitive sense of whether you want to work with each freelancer or not. I recommend making a list of questions for each candidate – noting their responses plus any major positive or negative points that arise. Being prepared for your interview will help both yourself and your candidate, and ensure your project starts off on the right foot.

Step 4 – Test Their Talents

This is where things get real. Where you put their skills to the test in a real, trial project. While this step isn’t necessarily obligatory, I couldn’t recommend it more. Whether the trial project is made up or genuinely part of the project is up to yourself. However, make sure you pay your freelancers! I can’t emphasise this enough. Expecting work for free is an insult to all freelancers – and will likely put off quality prospects in the process.

Instead, pay a small portion of your budget for one milestone to gauge their work. If you can’t decide between candidates, give them both identical work to complete. Make your judgement based on…

• Their communication (do they ask good questions? Are they timely? Do they keep you updated throughout? Did they listen and closely follow your initial brief?)
• The quality of the final work
• Their willingness and responsiveness to your feedback / edit requests

Once your trial project is completed, you should have a good idea of who you’d like to work with. Now, this might change as your project progresses. Make sure to break projects down into smaller, paid milestones to risk as little as possible. Choosing freelancers is nearly as important as selecting employees, and it may take a while to find the perfect candidates.

However, when you do, you’ll find that they’ll be a continual positive influence on your projects and your business overall. Who knows - once you nail the hiring process, you might find yourself replacing permanent roles in your company with experienced, dependable freelancers around the globe!