Over the past year, I have had the opportunity to work with some excellent technical freelancers. These relationships have been both professionally and personally rewarding. However, I also understand that for every one freelancer success story, there are many disasters. In fact, as a consultant, I have made a living out of cleaning up freelancer messes. Here are five tips to help you be more successful with your freelancers.
Don't use a freelancer to bring in a skill that you don't' already have in your organization
If you hire a freelancer to do work that your team doesn't understand, you are setting yourself up for trouble. First, you will have no way to evaluate his/her level of skill and the quality of work he/she produces. Second, you will not be able to maintain the code or systems that the freelancer builds when the project is done and she moves onto other projects.
Use a publicly hosted distributed source control system (DVCS)
Host your project on an externally hosted Git or Mercurial repository. This will allow you to try out freelancers with minimal risk. They can fork your repository and take on some development tasks and you can review their work before merging it into your own repository. If a new freelancer doesn't work out, just disable access.
Cast the net wide and filter
The only way to really get a sense of skill and compatibility is to start working with someone. People who look great on paper and can talk a good game are not always as competent as they appear. It is also easy to dismiss diamonds in the rough. Some of my favorite freelancers were very shy when I started working with them and would have been easy to overlook. With a DVCS and the ability to review work, you can assign development tasks to several developers and see who rises to the top. Just be sure to assign meaningful work and pay freelancers for their time.
Respect, trust, and communication are all critical to any relationship (personal and professional). Even though your working relationship with them may be shorter, treat freelancers with the same respect that you would give to a full time colleague. If the freelancer comes from another country, you have a great opportunity to learn a little about his/her culture and make a friend in a far away place. From my work with freelancers, I have seen a side of international current events that I would never see on CNN or the BBC. When you have these strong bonds, you get better commitment, better product, and a more enjoyable working environment.
Learn comfort zones
Everyone has their strengths and weaknesses. In a new working relationship, it is natural for anyone to underplay their weaknesses. Who starts a job interview by listing all the things that they stink at? The only way to understand someone's strengths and weaknesses is to assign a variety of tasks and see what comes back. Usually, people will start with the work that they feel most comfortable doing. Once you have recognized a few strengths and built a level of mutual trust, you can have more candid conversations about comfort zones. Some people like to focus on work they have the greatest confidence in doing. Others like the challenge of learning new things. The greater understanding you have about personality and comfort zones, the better you will be able to assign work and also evaluate work product. For example, if one particular developer likes to stay inside his comfort zone, you should just assign tasks within that skill area and you can be confident that the work will be done well. If a developer likes to learn new things, you can assign him challenging problems but you better have more rigorous quality controls.
I honestly feel like this is the future way of working. Through strategic and effective use of freelancers, you can make your organization more nimble and responsive. Companies that are not able to use freelancers will be slow to start new initiatives or avoid doing them altogether. On a personal level, you can learn so much by working with a diverse set of freelancers with different experience and styles. It is also nice to build new friendships — it's even more fun than having a pen pal.