A small business guide to hiring a freelancer for the first time

Need extra support for your business but not ready to commit to a full-time employee? Here’s how to find and hire a freelancer.

Hiring freelancers is a popular option for small businesses that need an extra pair of hands for a short amount of time. 

While we don’t want to mutter the “C” word before we’ve put our summer sandals away, many members of Enterprise Nation’s community are already putting plans in place for the busy season ahead.

Those plans include thinking about how they’ll manage increased demand, as well as investing more time and resources into digital marketing and PR.

If you’re considering hiring a freelancer but not sure where to start, here’s everything you need to know.

Managing your expectations

Enterprise Nation member and founder of Untapped FR Rita Peacock explains that it’s common to find working with freelancers daunting.

“Generally, the world of outsourcing can be challenging to navigate due to the level of work involved. Hence many entrepreneurs and small businesses tend to wear a lot of hats, particularly at the start of their business,” she said.

“However, when done right, working with freelancers can be great for entrepreneurs and small businesses. Not only does it save you time, it also gives you access to specialised professionals with expertise and experience who are able to perform the tasks that you are not familiar with.”

It’s important to know what to expect from a freelancer relationship before you start working with one:

• Freelancers will likely be working on multiple projects at once, so they won’t always be available

• Most freelancers work remotely, so you’ll need to “onboard” them remotely and trust them to get on with the job

• Freelancers will work in their area of expertise, rather than across the entire business

If you need someone to be able to do a bit of everything or be physically present in your business, it might be worth hiring an intern or hiring on a fixed-term contract.

Defining the extra support you need

Once you’re sure a freelancer is the right option for you, start by defining the scope of the tasks or project you need help with. That way, you’ll know exactly what kind of person you need and for how long.

Are you looking for someone to manage your social media channels? If so, will you expect them to simply post updates or do you want them to set up and manage digital advertising campaigns too? 

Remember, working with freelancers is a great way to access expertise you don’t have, so think carefully about what could be valuable to your business. 

Once you’ve outlined what needs doing, you can start thinking about the level of skill and experience you need. 

Enterprise Nation member and founder of SpareMyTime Melissa Gauge recommends keeping your desired skill set tightly focused.

“It’s very tempting to opt for someone who has a broad range of skills. However, frustration and disappointment will arise when a freelancer doesn’t have the appropriate skill set or experience,” she said. 

Researching your options

As a quick Google search shows, there are a huge number of large online marketplaces like Fiverr and Upwork where freelancers can list their services.

You’ll find that the services advertised on these platforms often have incredibly low rates. This can be for a number of reasons: the freelancer is new and inexperienced, based overseas or fitting small bits of work around studies or another job.

While it’s up to you to decide on your budget for freelance work, it’s usually a case that you’ll get what you pay for. 

A good option is to talk to other founders in your business network about which freelancers they’ve used in the past. You’ll not only find out if the freelancer is capable, but what they’re like to work with. 

You can also search for trusted small business advisers and services on the Enterprise Nation platform.

Choosing a freelancer

That brings us onto the next step: choosing a freelancer.

There’s no need to go through a rigorous hiring process like you would with an employee, but it’s still advisable to conduct some sort of interview. An interview gives you the opportunity to check their experience and, crucially, whether you’d work well together. 

“Request a discovery call with the freelancer,” Melissa said. “Be specific with your questions and ask about relevant experience. Don’t forget to consider softer skills too: do their values align with yours, are they emotionally intelligent and do they have a positive attitude?”

Melissa adds that you might want to start by setting them a small task. If you’re happy with the work, you can move onto bigger tasks; if there are challenges, you can check how they respond to constructive criticism.

The legal aspect of hiring a freelancer

Some people will confirm work with freelancers and agree on rates and deadlines over email. However, it’s always advisable to have a contract in place to protect both parties from misunderstandings.

A contract should include:

• The work the freelancer will be completing (be as clear about the scope as possible, rather than using broad statements like “digital marketing”)

• The time scale the work should be completed in

• The rate you’re paying and when and how the freelancer should expect to be paid 

Freelancers legally own the work they produce so contracts should also specify that the intellectual property (IP) ownership transfers to you once the freelancer has been paid.

Getting into the right mindset for delegation

If you’re delegating work for the first time, it can be hard to provide the right level of guidance without micromanaging. It’s especially difficult when it’s your own business that you’ve poured your heart and soul into.

Melissa recommends being as specific about your requirements as possible. The more specific you are, the higher the chance is that the freelancer will deliver what you want, how you want it.

“Don’t make assumptions. Even if your freelancer is highly experienced, don’t assume that they will know exactly how you like things done; time taken explaining is time well spent. 

“It’s important to communicate too. Schedule regular check-in sessions to understand your freelancer’s progress, to refine deadlines and tasks, and to provide feedback. Make sure your meetings are short and to the point. By communicating often and well, you’ll be able to improve productivity,” she said.

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