The New Dream Team: Building a Successful Team of Freelancers

57.3 million people. That’s how many freelancers there are in the U.S. However, it was expected that by 2017, the majority of the workforce will be made-up of freelancers. Now? 48 percent of people are already freelancing.

That’s all well and good. But, how does this large percentage of worker becoming freelancers impact you as a business owner?

If a majority of the workforce are composed of freelancers, then at some point you will have to start working with freelancers. And, that’s actually not a bad thing for your business.

The Advantages of Building a Successful Team of Freelancers

Here are the pros of having a freelance team for your business:

  • Instead of hiring and maintaining a full-time staff, you only have to hire people to do a specific job when you need it.
  • Since freelancers are independent contractors who you pay a set rate (either per hour or per project) for a set period of time you’re not responsible for their medical or insurance costs.
  • You can work with freelancers from all over the world. This can save you money, as well as deepen your talent pool and diversify your team.
  • You no longer have to hire expensive consultants if you only need an expert to help you work on a short-term project since freelancers are more affordable and just as knowledgeable and skilled.
  • There’s no longer a need to rent large office spaces since some, if not all, of your team work remotely. That can help your business save a ton of money. One report found that remote workers can save companies $10,000 a year in real estate.
  • You no longer have to be concerned about the cost of employee turnover.
  • Since freelancers set their own schedules, absenteeism is a problem of the past.
  • You can hire or fire as needed depending on how your business scales.
  • Remote workers are more productive.

Of course, there are also some disadvantages. Freelancers aren’t as familiar with your brand. Because they work remotely, you can’t schedule face-to-face meetings as easily.

However, make it a priority to get that face to face meeting.

Management can also be an issue thanks to language and location barriers, as well as knowing how to motivate them because they have different priorities.

Despite these challenges, the pros far outweigh the cons for hiring a freelancer.

However, the only way that your business will be able to get the most out of freelancers is by learning how to build and maintain your freelance team by doing the following.

Determine Your Wants and Needs

Before you do anything, take a moment and think about your preferences. For example, if you expect to be able to reach your freelancer during the same hours you work, then it wouldn’t make much sense to hire a freelancer who lives on the other side of the world.

Here’s some things that you’ll want to consider before hiring a freelancer:

  • Do you require your freelancers to be in the same time zone as you are?
  • Should everyone on your team speak the same language?
  • Do they need to be native speakers of your language? Or, will a basic understanding work?
  • How will you manage their tasks and workload?
  • How will you be able to communicate with them?

Also think about your business processes and internal systems like meetings and rules and guidelines. After you’ve taken all of this into consideration, get them out of your head and into something like a Google Doc. This way you have it for reference and can it share it with your new freelancers so that you’re not constantly repeating yourself.

Keep a tight picture in your head about what you actually need.

Additionally, you also need to assess where you need help. For instance, if you need to hire content writers, then you would look for freelance writers who are familiar with your industry.

While freelancers work are in a variety of industries, it does help to know size of the talent pool before searching for freelancers. It gives you a better idea on if you can find someone who can meet your specific needs.

Here’s the percentage of freelancers in various industries:

  • Development – 26.4 percent.
  • Sales & Marketing – 16 percent.
  • Design & Multimedia – 15.8 percent.
  • Administrative (Virtual Assistants, Data Entry – 14.3 percent).
  • Writing & Content – 12.1 percent.
  • Database & IT – 9.4 percent.
  • Others – 6 percent.

Finally, after determining your wants and needs, you can narrow down your search.

You could ask colleagues working in your industry if they can refer you to any freelancers or you can search on niche sites. For instance, if you need a freelancer to design a logo or website for you, you could search 99Designs since it’s a graphic design marketplace.

Find the Right Freelancers for Your Business

Like hiring full-time staff, finding the right freelancers to hire for your business is key. As explained by Choncé Maddox in a previous Calendar article, “Working with the right team members can catapult the success of your business because you’ll be able to essentially double your workload and your profit by passing off tasks to other people.”

So, how can you find the right freelancers for your business? Here’s some pointers to keep in mind.

  • Ask around. If there is someone you know who has worked with a specific freelancer, ask for an introduction. Do you know any freelancers? See if they know any other freelancers who can help you with your specific needs.
  • If there aren’t any personal recommendations, search reputable freelance job sites like UpWork, FlexJobs, or Fiverr. Here you can review ratings and client feedback.
  • Post a gig opening on not just freelance marketplaces, but also social media and Craigslist.
  • Don’t always go with the cheapest option. While you may find a freelancer just starting out, so their rates aren’t high yet, you often get what you pay for.
  • Check to see if the freelancer has a website and is on social media. This allows you to view samples of their work, as well as get a better understanding of their personality.

Schedule an Interview With Candidates

When you’ve found a freelancer that has the skills you need and appears to be a good fit with your culture, go ahead and schedule an interview with them.

You can interview your freelancer face to face on many different sites.

Obviously, you can’t do this in person. But, you can schedule a Skype interview with them. This will give you a better sense if they have the skills and personality you’re looking for before you hire them.

To make this process as painless and smooth as possible, here’s some pointers to keep in mind:

  • Use a scheduling app. This way you and the freelancer aren’t wasting time trying to find a good time to have the interview. Just share your calendar with them and they can select an open slot. The event is then added to everyone’s calendar automatically.
  • Conduct a proper interview as if you were hiring an in-house employee. This allows your to assess their hard and soft skills.
  • Always ask for samples of their work and references.
  • Take a couple of minutes and talk about something non-work related to see if they are a good fit for your organization.

On-Board New Hires

Congratulations! You just hired a freelancer. But, your work isn’t done just yet.

You now have to properly onboard them by explaining your company values and culture, introducing them to other team members, and agreeing on principles, such as how often you’ll check in with each other and the best way to communicate.

Keep your brand fresh in their minds.

Don’t forget to also brief them on your brand. For example, if you recently hired a content writer, then make sure that they’re familiar with your tone and voice.

If this is for a one-off project, you don’t have to be concerned with this. But if you anticipate that you’ll be working with them for an extended period of time, then make sure that you take the time and effort to properly onboard your new freelance hires.

Manage Your Virtual Team

Managing a remote team is no-easy task. It’s not like you can walk around the office and check-in on them or just have a friendly chat to build rapport.

Thankfully, there are effective ways to manage a virtual team — whether they’re freelancers or full-time.

  • Set clear expectations.
    “When you manage remote employees you need to establish the same guidelines as you would for any employee. From the get go you need to set clear expectations,” says Renzo Costarella. Include details “like what are required hours of availability, acceptable lines of communication, and any penalties for abuse of the policy.”
  • Have reasonable deadlines.
    It’s not fair to assign a freelancer a task in the morning and expect them to have it completed by the end of the day. After all, they may be working with another client or it’s off-hours for them. When you have deadline to meet, give them fair enough notice.
  • Use cloud-based tools.
    Technology now allows everything from calendar management to invoicing to communication to be done through the cloud. You should also find a project management system so that you can assign, monitor, and track your freelance team’s work and progress.
  • Build personal relationships.
    Schedule one-on-one meetings with your freelancers. This could be a monthly Skype call where you discuss anything from their family, hobbies, or interests. It makes them feel valued, while also bringing the two of you closer.

Keep Your Freelancers Happy

Finally, if you want your freelancer team to be more successful, than you need to keep them happy by:

  • Being responsive.
    This means responding to them in a timely manner and not going MIA for several weeks. You wouldn’t expect them from them. What’s more, you wouldn’t treat the rest of your team this way either. Always keep the lines of communication open and be transparent.
  • Make them feel valued and supported.
    Offer praise and constructive feedback. Provide opportunities for them to grow personally and professionally. Invite them to team meetings or even represent you if there’s an event near where they live.
  • Fair and timely payments.
    Offer your freelancers a competitive wage. Also, always pay them on-time.
  • Create contracts.
    This builds trust and puts both of your minds at ease. This ensures your freelancers that they have job security, but it also guarantees that they’ll complete a project by the due date.

The New Dream Team: Building a Successful Team of Freelancers was originally published on Calendar by John Rampton.


  • John Rampton

    I write about interesting startups.

    Hey, my name is John Rampton. I’m a serial entrepreneur. I love helping people in addition to building amazing products and services that scale. I'm currently the CEO of Calendar. John was recently named #2 on Top 50 Online Influencers in the World by Entrepreneur Magazine as well as a blogging expert by Forbes. Time Magazine recognized John as a motivations speaker that helps people find a "Sense of Meaning" in their lives. He currently advises several companies in the bay area. John loves helping others succeed online. It's all about helping and giving back. It brings me joy in my life. You'll also find that when you give to people that it always comes back. You can connect with me @johnrampton. I blog about my success and my epic failures on Entrepreneur, Forbes, Inc, TechCrunch, Mashable, Huffington Post and many more.