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4 Tips for Hiring a Winning Freelance Team

Freelancing. It’s what more and more working-age people want to do. Hiring freelancers. It’s what more and more companies want to do. And the growing trend says that both will have their wishes met for years to come. Many, in fact, already claim that working in an office is essentially “dead.” We have a new breed of workers – millennials who have been connected since their toddler years and who see no need to report to an office at 8 a.m., stay until 5 p.m. and then fight the commute home. They need an internet connection and a workspace, and that can be anywhere in the world.

Just how common has freelancing become? The known figures are as follows: roughly 1/3 of the American workforce (about 53 million) are now labeled freelancers, either part- or full-time. In the UK, the number is 1.4 million; and in Europe, that number has risen to 8.9 million. Figures for other parts of the world are not exactly known, but in emerging economies and globalization, more and more skilled professionals are operating in a freelancing environment.

4 Tips for Hiring a Winning Freelance Team

Securing That Freelance Dream Team

Business owners do not go into the arena of using distributed teams/freelancers without concern. They do not physically see their “employees” every day and gauge their work productivity; they worry about hiring the right people who can work well together in a remote environment, communicate, and support one another. All of this means developing a plan and a process for finding those “right” people. Here are 4 tips that should help.

Develop Your Set of Interview Questions in Advance

This will help you focus on the skills and traits that you know you will need. Of course, there are common interview questions that you would ask any interviewee, and those should be included. Beyond that, however, you will need to know what successful freelance experience is in the candidate’s background and who you may verify that success with. Beyond freelance experience, however, you will need to assess the candidate’s experience working remotely with a team. Again, you are looking for successes that you can verify.

Finding The Candidates

Now, where to look. Of course, you can check out some of the huge freelance job boards, but you might want to consider some more targeted sources.

  1. LinkedIn is a great source, and you can narrow your search pretty quickly just by reading resumes and asking for recommendations
  2. Use your network. If colleagues within your niche have had experience with individuals who have the skill sets you need, taking their recommendations can put you in a good position.
  3. Post your needs on other social media channels. Facebook groups, for example, provide excellent sources of individuals with specific skill sets that you need.
  4. As you hire a freelancer, ask for their recommendations for your additional specific needs. A content marketer, for example, may have worked with an amazing freelance IT pro in the Ukraine or web designer in India.
  5. Check out professional organizations. They tend to have their own smaller jobs boards that you can utilize.
  6. Access niche jobs boards – they are all over the web. Most have a global reach.

Conduct Your Interview via Skype of Other Such Platform

Employers can learn a lot about a person from a face-to-face interview. Facial expressions, non-verbal behaviors, etc. are important, and you want to “see” and talk with the candidate no matter where they are located. Always conduct your interviews with a tool that allows face-to-face sessions.

If you have already hired some of your distributed team members, bring them in on at least part of the interview. You want to see the interaction so that you can evaluate a candidate’s ability to communicate and “fit in” with the existing team. If the beginnings of rapport are observed pretty quickly, you probably have the right person.

Expectations in Writing

Prior to the interview, you have obviously posted the job requirements and skill sets you need. More than that, however, you need to provide any candidate with a full set of expectations that go beyond just the skills you need. Workplace policies are not just for in-house employees. What are our expectations in terms of communication? How will this individual report progress to both you and to other team members? When will there be meetings? How will you handle the time zone differences? All of these things need to be in writing, up front, so that there are no misunderstandings, should the person be hired.

Companies Love It

Obviously, there are some business niches that cannot go fully outsourced – we still need medical staff on site in hospitals; we still need workers on site in car plants, and we need sales clerks for shoppers who still enjoy the brick and mortar experience. But these niches, too, will be disrupted as technology marches forward, and the numbers of freelancers will increase.

There are big benefits to companies that can use freelancers:

  1. Affordability: when a company does not have to employ full-time staff with salaries, benefits, and workspace requirements, the overhead costs of doing business decrease.
  2. Greater Flexibility: Freelancers can be hired and terminated at will, without any concern for laws and regulations and the potential for lawsuits.
  3. Distributed Teams: Companies can look to find experts from all over the world to meet their business needs. These distributed teams can collaborate whenever the need arises, and yet work independently on their task responsibilities. When companies do not have to confine their employment search to a single metropolitan area, the potential to find just the right specialists increases.
  4. Improved Productivity: Distributed team members all have their parts to play in the overall mission and goals of a company. They also know that they can be terminated at will. Add to that the flexibility to determine hours that work best for them, they are more productive.

While many companies are experimenting with and using distributed teams for specific projects, others have adopted the model entirely – Automattic, Basecamp, and Buffer are just a few examples.

If you are new to outsourcing and/or developing a distributed team, you will not be the perfect leader/manager immediately. You will learn as you go. You will make hiring mistakes, and you will correct them quickly. But in the long run, you will ultimately learn how to put together effective and even amazing teams that will meet your mission and goals.

Image: Man working on desk and writing Freelance


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Elena has been working in the digital marketing industry for the past 5 years, first as a cubicle dweller and now as an independent marketing consultant and copywriter. She has a knack for elegant traffic growth hacks, requiring little (if any) investment and creative content marketing.

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