Building a Team with Freelancers


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Last Wednesday I heard Will McInnes of Nixon McInnes and Barry O’Reilly of ThoughtWorks talk on what a good product development culture looks like. After the excellent talks, someone asked the obvious question for most companies involved in software development:

How does culture building work when your team of developers is based in different countries and working remotely?

The panel’s response was “it’s tricky”, but I believe there are ways to build a ‘distributed culture’ in a small business. Using remote freelancers is a sound way to hire experts without a large bank balance, and bringing them into your company vision culture is the best way to get long-term loyalty.

At Teachable we have worked with a brilliant group of freelance editors, designers, web developers and marketing managers over 4 years. Some have been short contracts for specific projects and others have kept a long-term relationship with us doing part-time work. They have been a diverse mix of ten nationalities working out of UK, Ireland, Spain, Holland, Italy, India and Sri Lanka.

Yet we have tried to foster a sharing mission and working style to motivate and engage this remote, evolving team. Here are my tips:

1. Sell freelancers the big vision

The frustration for many freelancers, especially those working through marketplaces such as Elance, is that they work on a stream on unconnected, specialist projects without seeing how the contribution to the whole business. Imagine asking an artist being asked to paint the sky within a painting, without showing them what the whole picture is of.

Recruit your team by telling them what you are aiming for, and candidates might even refer you customers. Tell them why their small role is important, and how what successful work would mean for your organisation and its customers.

2. Pick team-workers

Many software developers are recruited using narrow assessment of their fluency in a certain programming language. Yet I find the way developers communicate, and especially how they ask for clarification or support from other team members, is a better gauge of how effective they’ll be.

Set your remote workers a test project, which can’t be completed fully without collaboration and see how they respond. People who get stuck and can’t / won’t ask for help, or (worse) insist their non-collaborative solution is the correct one, will not improve your culture.

3. Find time for regular phone or video dialogue

Working with people in a different time zone or native language presents further challenges. Leaving all communication to (overnight) email often leads to major misunderstanding – most critically in the timing of delivery, if the contractor is working on multiple projects.

Skype is your best friend here – organise a regular (weekly for most of our team) group call. But make sure the time is spent in hearing their issues, not just passing on instructions of what to do next.

When contractors are paid by the hour, there can be a mutual feeling that ‘project management’ time is dead time: you have to be willing to pay separately for this communication time and appreciate it improves the productivity of the other time.

4. Keep the team informed

When initially promising freelancers have not worked out, we have often failed to keep them informed as the project evolves. This feeds into a regular call (see above), but can also be solved by a weekly update email – which includes all the personal and business developments they would have picked on by being in an office.

For the software developers themselves, we have set up automated group emails from our continuous integration server so tell them what any of the rest of the team has changes in the code base.

5. Reward loyalty

When work is priced by the hour, and a cheaper worker is only a few clicks away, it can encourage a ‘hired gun’ attitude of complete and move-on. But there are real costs for freelancers finding new clients, and for you inducting new people into the shared culture. So making clear that you want to build a long-term relationship, and being generous with completion bonuses and pay rises, is really in your interest as an employer. It also helps the rest of the team to invest in that individual if they are around for a while.

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