How nearly two decades of freelancing shapes Distributed today

By Cal Adamson

After 17 years of building and managing freelance teams, I’ve come to realise that the key to unlocking an outsized level of quality and speed lies at the intersection of two crucial factors: team-problem fit and team-cultural fit.

If you can build the team best suited to solve the problem you’re tackling, and if that team is culturally aligned with each other and the business they’re delivering for, you are almost certain to deliver faster and to a higher standard than a team that is simply “available.”

What is team-problem fit?

It’s essential to understand the concept of team-problem fit. This refers to how well the skills and expertise of your team align with the problem they are solving. A software development team may consist of the best programmers in the world, but if they’re not experienced in the language, framework, or industry the project requires, their effectiveness diminishes.

What is team-cultural fit?

The other half of this equation is team-cultural fit. This relates to how well team members can work together, given their personalities, work habits, and communication styles, and how that matches up with the end customer. A team that communicates effectively and respects each other’s working styles can easily outperform a more skilled but less harmonious team. 

Encouraging a culture of respect, collaboration, and open communication is vital in any team, but perhaps even more so in a freelance setup where individuals may be spread across different time zones and cultures.

It’s taken a lot of failing forward and experimenting to achieve the simplicity of focus in those words. I still remember the first freelance team that I assembled (this was back in the days of Elance and oDesk) to build out a small application for ASOS (back when ASOS only sold stuff that people wore in films, like Morpheus’ glasses from The Matrix, ‘As Seen On Screen’) as they were experimenting with mobile websites, which were a new concept at the time. 

The tech stack used to assemble, communicate, and pay the team was unbelievably primitive compared to today’s standards. Skype, Excel, PayPal and SCCS made up almost the entire delivery suite. As a team, we delivered the test mobile application (after overcoming many technical and cultural problems) which never actually went into production, and ASOS eventually went on to become one of the most well-known e-commerce platforms on earth. I’m still in touch with a few members of that team, and from last reports, they’ve gone on to have exciting and successful careers as remote software developers.

So much has changed since those days. The technology that enables globally distributed teams to be recruited, qualified, managed, paid, and connected has seen dramatic advancements.

This has led to an enormous rise of freelancing. In 2010 it’s estimated that around 20 percent of the US population were freelancers; that number is now at around 40%, representing an increase of over 100% in the past decade, which is a staggering increase for any industry.

There are now countless talent clouds and freelancer marketplaces to choose from, and equally as many project management tools, communication platforms, payment providers, and security systems to ensure working with globally distributed teams of freelancers is as easy as working with your core on-site teams.

While advancements in technology have allowed for a myriad of choices for infrastructure to manage your remote freelancer teams, what truly drives value is how these teams are recruited, assembled, and managed. There are several best practices to consider.

Firstly, in recruitment, look for problem-specific skills rather than general abilities.

Deep expertise in a specific domain often trumps general competency. Use platforms that allow you to dive deep into a freelancer’s skills, past projects, and ratings from previous clients. Furthermore, leverage AI-powered tools that can quickly scan through numerous freelancer profiles and match you with candidates that fit your specific needs.

The next step is the assembly of the team. Here, the essential principle is to consider the balance of skills and personalities. You might need freelancers who are subject matter experts in their respective fields, but you’ll also need generalists who can connect the dots and maintain the cohesion of the team. The perfect balance varies with each project, but a good starting point is to build a core team of specialists supplemented by capable generalists who are all culturally aligned and complimentary from a personality perspective. You’re building a problem-solving machine; each part needs to work harmoniously with the others.

Effective management of remote teams requires both discipline and flexibility.

Managers must enforce clear communication practices and ensure regular updates are made on project management platforms. This can prevent misunderstandings and keep everyone aligned on the project goals. However, flexibility is also key, considering the varied time zones and work schedules. It’s important to foster a culture of respect and understanding where everyone is empathetic to the nuances of remote work. Incorporating asynchronous communication tools like Slack or Microsoft Teams can help facilitate this balance.

And, while you may now be geographically dispersed, don’t neglect the human aspect of your team. Schedule regular virtual team building activities to build rapport, foster camaraderie, and reinforce a shared team culture. This can be as simple as virtual coffee breaks, game sessions, or even shared online workshops.

Periodic feedback and recognition are also crucial. In the hustle of meeting project deadlines, don’t forget to appreciate the efforts of your team members. A small message of recognition can go a long way in boosting morale and productivity.

Successful freelance teams, just like traditional teams, are built on trust.

As a manager or business owner, your role is to trust your team and their expertise, give them autonomy, and provide support when needed. This not only empowers your team but also creates a positive work environment that promotes quality and efficiency.

As I look back on my journey over the last 17 years, it’s the gifts, performance and the personalities of the people I’ve worked with that stand out, and that made the difference when it mattered, not the systems or the technology. In this ever-changing world, that’s the one thing that will always remain a constant, the better the team, the better the outcome.