Building a Team with Contractors and Freelancers

Building a Team with Contractors and Freelancers

What makes a great team? Henry Ford once said, “Coming together is a beginning. Keeping together is progress. Working together is success.”

That quote got me to thinking about the 21st Century version of a small business team.

Usually, we think of a work team as involving employees.

However, today’s small business teams are likely to consist of a business owner working together with a group of freelancers and independent contractors, instead of employees.

The people in such a team are working at a distance, from their own offices. They may be across town, across the country or across the globe. This makes communication challenging.

They may work together on certain activities, but typically each is pulled in different directions on any given day. Remember that each freelancer or contractor has his or her own business and other customers to contend with.

And when you are paying someone by the hour or paying a retainer for a set menu of duties each week or month, the business owner may hesitate to include the contractors in conference calls, email distributions, or meetings out of respect for the contractor’s time. After all, time is money for most freelancers and independents. We small business people understand that.

How do you develop this kind of “virtual small business team”?

I searched websites, article directories, and blogs.

I can find information on hiring freelancers or subcontractors. What I find very little written about is how to make freelancers and contractors feel part of the team — or about communicating and working cohesively together when you are a group of contractors.

Yet — shouldn’t contractors and freelancers be part of the team?

I looked around for advice on how to build a traditional team. Perhaps these resources offer some clues:

Reward teamwork behaviors — Perhaps we should be offering bonuses for team results. Tonya Vinas recommends rewarding teamwork behaviors with money, in Small Business Team Building:

If building a team around results — units produced, cost reductions, meeting deadlines — include a monetary reward tied to the results. Money is a great motivator. Offer bonuses, compensation or other rewards for a great team performance.

Have clear goals — Do we as business owners have a clearly defined mission and set of goals for the team? Susan Heathfield writes in 12 C’s to a successful team:

Has the team taken its assigned area of responsibility and designed its own mission, vision and strategies to accomplish the mission. Has the team defined and communicated its goals; its anticipated outcomes and contributions; its timelines; and how it will measure both the outcomes of its work and the process the team followed to accomplish their task? Does the leadership team or other coordinating group support what the team has designed?

Treat it as a self-directed team — Since everyone is an independent contractor in the team, shouldn’t we be considering this a “self-directed team”? Jeanne Dininni points out that this is a different style of work performance from a traditional team, in her Guide to Self-Directed Work Teams:

Prepare your staff for self-directed team membership with some training of their own. Training your managers isn’t enough. You’ll also need to see that the team members, themselves, are thoroughly trained, developed and prepped for the exciting, though serious, responsibilities ahead. Effective training will equip them to be productive members of the team.

Also helpful is an article by David Chaudron, Ph.D. entitled Nailing Jelly to a Tree: approaches to self-directed work teams. Just the title itself should let you know Dr. Chaudron’s feelings on the success rate of self-directed teams. However, I think he is just saying that if you just state “Pow — you are now a self-directed team” and then walk away, that you can’t expect the participants to be successful. It sounds like a fine line.

For those of us trying to build a team with freelancers and independent contractors, how do you do that? Share your practical tips for building a sense a teamwork among a loosely-tied group of contractors.

Image: Shutterstock


15 Reactions
  1. I think it is important to make each person feel like part of a team. Maybe by a once monthly short meeting to talk about that month’s accomplishments and next month’s goals. Giving them contact with each other also and not just each person contacting the “boss” on their own. This helps open up communication and would maybe encourage them to help each other more like team members.

  2. I have always thought that this was an effective idea, but the problem lies in trying to find really good individuals who are willing to put this sort of approach into their personal business model. Team building is all well and fine as long you can get past this first major step.

  3. You are right – creating a team is a challenge with freelancers. I have worked with a woman who owns a marketing business built on the work of subcontractors – all women. She does something a little unique. Each year she brings them all together for a “hookie” day in which they gather at her home for muffins and beverages and all go to a spa for a day of pampering. I have worked for her on occasion and had the priviledge of participating in the event last year – it was a great way to meet face-to-face all of the team members that create the product her customers receive. The mere act of getting together in person helped to foster that team feeling and begin the process of creating relationships. It was a great experience and I believe it has helped her create a cohesive team.

    Of course that’s just once a year. Paula’s idea of monthly is a possiblity. Of course – finding the right individuals, as Scott points out, is also critical. However, isn’t that the case with creating any team? Gosh, if only the world were made of people just like me.

    Scary thought. 🙂

  4. Something so simple but so effective is to be sure each contractor, freelancer is a part of the small business owner’s email with each having their own company email address. This way, it presents a common face to the client and all are included in all relevant emails.

    And, of course, a bi monthly, roundtable conference call, going around with each team member talking about what they worked on and successes, discoveries. Worth every minute of time.

  5. Deborah Chaddock Brown

    Hey Kathleen – what a great idea. And so valuable to have that united front for the customer. What about a Yahoo forum for communicating within the group? Does that work or is it just more email floating around?

  6. Trust in their abilities, in time of course. Once you are aware of how well someone works, trust in their capabilities to deliver. In you don’t trust and have faith in them, then the relationship won’t thrive.

  7. One thought about virtual teams is to rely heavily on online collaboration tools. some are easy to put into play (shared Gmail account, or virtual switchboard software, for example). Other tools take a little extra work to think through.


  8. Martin Lindeskog

    I learned from my studies of international project management (coordinator) that it is good to have a kick-off when you start a project and gather every member and also have an event when the project is finished and it is time for evaluation and feedback. I think you could create a sense of belonging to team, but at the same time be and independent actor, by using the tools Anita is listing.

    I have said it before, but I want to reinforce the idea of a new way of being “employed”. Look up the term “business employment” and “reverse staffing company” and “hire your own employer”. For an example, check out this site:

    I have seen great examples of how to build teams in the network marketing industries. There you are often an independent distributor of products or services with an “upline” (sponsor / mentor) and a “downline” (customers). Together you are creating matrix of team members.

  9. Deborah, I love the story you shared about the hookie spa day. That’s inventive! But as others have stated, communication is the most important part. Regularly scheduled talks or meeetings are a must in a situation like that. It’s absolutely necessary to come together like that every once in a while. Otherwise, the left hand may not be aware of what the right hand is doing and then complications arise. I think it’s also very important to inform your team, each and every member, of exactly what there duties are and exactly what’s expected of them. Because at times, they may be feeling their way around in the dark.

  10. Ahhh Communication. Isn’t it the key to everything in life?

  11. Martin Lindeskog


    I agree with you! Here is a new way of communicate in a personalized way. Use a video email system called Talk Fusion. Nothing bad to say about YouTube’s popularity, but if you are interested to have a personal touch or use a message according to your company’s graphical profile with logotype, colors, etc., I would recommend you to check out this professional provider of a great communication concept. If you want to see and listen to a summer greeting by yours truly, EGO, please click on the following link:

    How about sending a audiovisual note to your project / team members, contractors and freelancers now and then?

    All the Best,

    Martin Lindeskog
    EGO blog

  12. I am in both sides of the table now. On the one hand, I am working as a contractor and freelancer and then, I have to manage a team of 4 freelancers who work with me on a day to day basis.
    I am very happy with my team because they are serious and committed to any project just like I am. Well, I have to admit that I know all of them for a long time and that is perhaps why, I face hardly any problem with my team. I have managed to convince them that with me, they will have the best prospect. So, I am never afraid that they would jump to another place for some more money. I think that this is the biggest challenge while working with a team of freelancers.

  13. Thanks, Razib, for your relife example of how it can work. Sounds like you are creating a family or a partnership experience with your freelancers!

  14. Interesting stuff here… leaves me thinking. Some people are not exactly doing the stuff they are naturally good at or even passionate about. It is a job to them. I think in this instance, the formula does actually work so well as each team member needs contribute 110% to really turn any small business ideas to big business returns.

  15. Good article with an excellent way of presentation. Keep it up. Thanks for sharing.