10 Tips to Consider When Hiring a Freelancer

There are many costs associated with running a business, and the majority of businesses require staff and employees in order to succeed and function on a day-to-day basis. As costs rise, many companies are hiring freelancers and outsourcing some, or not all, tasks.

With so many online platforms to find readily available talent, it leaves many business owners wondering how they can avoid making mistakes that will cost them valuable time and money. While hiring the right freelancer can cut costs significantly, the wrong one can end up costing you more in the long run.

Here are ten tips you should take into consideration when hiring a freelancer for your next job or task.

1. Make sure your expectations are clear from the beginning.

“As a former product manager responsible for the output of 50-person teams, the key recommendation I have for working with freelancers is the same as for working with an internal company team: Set very clear expectations and always manage to them. Some of the best time spent is to be very diligent at the beginning of a project to spec out what the framework of the engagement is and what the final product should look like. Before you immediately ‘run’ and start the project, determine how often and with what method you will be communicating with your freelancer.

Next, determine the outcome, meaning what the final result should be. Do this in excruciating detail. Force yourself to really think about the ‘what if’ scenarios.

Once you have the end goal documented, ask the freelancer to come up with a project plan with a few milestones in it. Also, ask them what they need from you — this is a two-way street. Describe those milestones clearly and then tie 50-70 percent of the cost to the intermediate milestones with 30-50 percent to the final one.

It may seem laborious to do all this upfront work and not immediately dive in, but setting proper mutual expectations is key to on-time and on-budget project delivery.” — Tim Trampedach, founder and CEO of Torqued

2. Define the project and include a scope of work.

“As a freelancer, I’ve been approached many times with what people want me to ‘do,’ without the ‘why’ explained. If the underlying goal of the project isn’t clearly defined out of the gate, it can be challenging for a freelancer to be ‘fully onboard with the team.’ Not only explain what you want the freelancer to do, but why it’s important to your business, what you hope it will accomplish, and how he or she is adding value.

Adding value leads us to the scope of work. Clearly defining what you want the freelancer to ‘do,’ along with the ‘why’ mentioned above, can help increase efficiency, and potentially identify new ideas or approaches.  — James Bowen, Ripen Digital

3. Create opportunities based on freelancers’ specialties.

“My company is an all-freelance team. Our team is comprised mainly of work-at-home moms. I have hired all 20+ Momosa team members ‘backwards.’ When I meet people who would be great additions to our team, I create opportunities for them, rather than identifying opportunities and finding the people.

This method has worked successfully for me for 10 years. Early on, our team members were ‘Janes of all trades’ — I assigned tasks to whoever was available as the tasks came up. As we’ve grown, I’ve began creating specialties for our team members: Review Director, Social Media Director, Writing Director, etc. This has led to more efficiency and cost effectiveness.” — Jennifer Bright Reich, Momosa Publishing LLC

4. Understand that communication is first and foremost.

“In order to hire freelancers, make sure that you are clear with communication first and foremost. It’s absolutely essential that the freelancer understands what you’re looking for, and that you both are making the same assumptions. When you work with a group of people, it can be easy to build work patterns, but any new member joining your group (especially freelancers) won’t have this. So, make sure to specify exactly what you need done, how, and what you’re expecting in the end.

Make sure that you have a clear and open compensation system, both understanding how compensation will be measured, and how everything will be tracked. It’s important to make sure that whomever you’re working with understands what is included in work, what isn’t and how the time should be measured.

For example, if you have someone doing data entry, it’s important to make sure that you mutually agree on what’s the best way to determine the amount of work done (for example, a precise measure of how much data has been entered), and what the compensation is (in this example, $2 for every 10 rows of data entered). This makes it clear what is required and what will be received in exchange for the work performed.

As you progress through the freelancer’s work, issues will arise, at least in my experience. It’s essential that you are open with your freelancer about what these issues are, and that you don’t criticize them coming to you with questions. This may sound obvious, but some business owners will become angry if too many questions are asked (especially if they are busy), and if the freelancer isn’t autonomous enough.

Providing negative feedback will degrade the relationship you’re working to build with your freelancer, so make sure that any criticisms are presented in a positive manner. Make sure everything is presented as means for improvement. This will help you develop a strong relationship with your freelancer for the long-term, avoiding the costs of re-hiring people and developing the relationship over again and again.” — David Selden-Treiman, Director of Operations at Potent Pages, LLC

5. Give specific instructions when sourcing applicants.

“I’ve hired freelancers from all over the world, in a range of skill and pay brackets and I find two things work really well in weeding out the poor applicants.

First, I always get applicants to write a particular word in the subject line of the application email. I pick a fairly random word like ‘Frog,’ I don’t give further instructions on how they should use it in the subject line.

Some people just enter the subject line: Frog.

Others are creative or funny with it, and I tend to find these applicants turn out to be a better fit.

For anyone who doesn’t use the word I assign — I ignore their application, as I’m looking for the ability to follow simple instructions and those who pay attention to detail.

The second thing that I’ve found really useful is making applicants complete a small test of 5 or 10 questions that are somehow relevant to the job they will be doing.

For example, when I’m hiring virtual assistants that will be handling emails, I’ll ask them a few questions about email etiquette.

Then I’ll ask some fairly random questions that test their ability to work on their own and solve problems. An example question I often ask is ‘What does CR7 mean?’

A quick Google search will tell you it’s generally associated with Cristiano Ronaldo and his jersey number, but it’s surprising how many people come up with other answers, that are not necessarily wrong, but not what I expected.

Asking random questions like this that are somewhat ambiguous quickly shows you how confident your applicants are in owning their answers, which is a simple proxy of showing how confident they may be in their work.” — Marcus Clarke, Searchant

6. Put your expectations in writing.

“One thing I have learned over the years is that people love and respond to clarity. This has proven to be true in my interactions with hiring freelancers.

There is immense value to be added to businesses of every size and industry by working with freelancers. Hiring freelancers, allows you to get projects done by people who have knowledge about a specific area of work without having to add another employee to your payroll. This is especially useful for small businesses as they grow.

However, I have found that initially there is trial and error when it comes to hiring freelancers for various tasks. Each person has a different approach to their work and the way they interact with you as the person hiring them to do the work.

You will find there are excellent, average, and just plain terrible freelancers out there. The best thing to remember is that you are the one paying them, and you determine the expectations. Expectations to be outlined include the price you will pay, the scope of the work, communication preferences, and the timeline associated with each project.

I like to put my expectations in writing and make sure the freelancer I am hiring is aware of my expectations and I always follow up to see if they have any questions or concerns.

Though you can never be sure of the outcome when it comes to hiring freelancers, this strategy has helped eliminate so many miscommunications leading to better work and longer relationships.” — Danielle K. Roberts, Boomer Benefits

7. Test thoroughly and fire quickly.

“As the owner of two web development agencies that have relied significantly on freelancer workers, my number one tip for hiring freelancers is to test thoroughly and fire quickly.

When I need to hire a new freelancer, I will always start them out with a small task with a client that does not care about strict deadlines. By doing this, I am able to test out their ability in a low-stakes environment. I will route all communications from the freelancer to the client through me to ensure that they are professional and accurately describe the work that has been completed.

Furthermore, I will carefully check all of their work to a level of scrutiny that I could never maintain on a full-time basis. In short, I do not trust freelancers, even those with glowing reviews, until they have earned it. If the freelancer delivers on time and on budget, I will give them detailed feedback on my thoughts on the test project and then offer them a new task that allows us to work towards establishing a longer-term relationship. If they do not meet my expectations, I will let them go without any second chances.

My rationale is that a person who cannot perform to expectations when they know they are being carefully scrutinized is not the type of person who is going to be able to consistently meet deadlines and deliver high-quality work once they are given the freedom to work on a larger project and set their own schedule. I used to be more lenient about this policy but was burned multiple times by people who would promise to do better the next time only to consistently underdeliver.” — Zack Gallinger, Talent Hero Media

8. Follow your gut feelings.

“When hiring a freelancer, the best advice is to follow your gut. You can (and should) do your research, look into their previous work, speak to their clients whenever possible, and get a very clear understanding of what your project will entail, what it will cost, and how long it will take. However, listening to your gut is even more important than doing your research.

A freelancer can post only the positive reviews and refer you to the happy customers, choosing to bury the negative testimonials and skew the feedback you’ll receive. What they can’t do, is influence your internal warning system. Have you ever met someone and it feels like your skin is trying to crawl off your body? That’s your intuition telling you to run and run fast!

We are biologically wired to sense danger (even if it’s not physical danger) and when your body reacts negatively, you need to pay attention. If you don’t like the person, or you get an uneasy feeling when talking to them, don’t ignore that. Sometimes, our bodies pick up on things that our brains don’t quite register. When you ignore those signals, you end up working with someone who is at best, not a good fit for your project, and at worst, dishonest and dangerous for your business.

The bottom line is to do business with people that you know, like, and trust. You’ll have a better chance of having your project completed in a timely, appropriately priced fashion, and avoid the disasters that come from ignoring your gut.” — Sheryl Green, Sheryl Green Speaks

9. Consider your ROI.

“When hiring a freelancer, the main thing to consider is the return on investment — is it going to be there if you hire someone for the assigned work. The best way to avoid getting subpar work is by being extremely clear and detailed when explaining what you need to have done. If there is going to be a lot of work involved, be clear, as this may not be the right person for the job and the last thing you want to do is hire someone only to have him or her get halfway finished and realize they can’t finish, requiring you to start all over.

Second, look for a portfolio of examples that the potential candidate has or feedback from others that have shared how their experience has been. Sometimes, looking for the negative reviews can be more insightful than all positive feedback.

You should also check to see if there is going to be numerous freelancers working on a small project together if they prefer doing a certain piece of content over another. Chances are if they prefer a piece of content over another is that they could have a skill set that can be used better when doing the certain task.

When looking on Fiverr, for example, they offer different levels of reputation depending on work done as expected, work is done on time and the amount of orders that have been completed. The minimum number of gigs you need to look for should be around the ballpark of 15-20 orders completed as they should know what to expect by this point in terms of delivering as expected.” — Michael Russell, Senior Director of Digital Marketing, Ratchet Straps USA

10. Have realistic expectations.

“In order to successfully hire a freelancer, you want to make sure you approach the situation realistically. This means you should be clear in what you expect from them and make sure you have a full understanding of what they can accomplish. Many times when it comes to freelance work it is hard to gauge when certain deadlines are met because of the nature of the work.. So that is why clear and realistic deadlines are so important. A great way to get to know a little more about your freelancer and set these goals and deadlines is to have a meeting before they begin the work.

This is a great time to come to an agreement with the freelancer as to what they feel is achievable, when you will check in with one another, explain how long the work will last, etc. This leads to the next step, which is to keep in constant contact with your freelancer. Communication is key if you want to keep your project running smoothly. This will ultimately set both you and the freelancer up for success in the long run.

After you have your meeting with your freelancer it may be a good idea to test out the waters with them. In other words, don’t give them a huge project right away. Give them a small task and see how they can handle it. Once you see they are fine with that task then you can add more work to their plate. Finally, remember a big part of a successful relationship between you and a freelancer involves feedback. Not only feedback to them but you must be willing to accept feedback as well.” — Andrew Rawson, Chief Learning Officer of Traliant

Jonathan Long is the Founder of Uber Brands, a brand development agency located in Miami, focused on building e-commerce brands in the health, fitness, lifestyle and beauty industries.