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Here’s the one thing that could make or break the growing freelance economy

Project-based workers cost less and give companies a competitive edge. Can a new role mitigate the risks of outsourcing?

I’ve worked with hundreds of freelancers in my career. I’ve tackled big projects with freelancers and pitched alongside them to win new business. I’ve learned from freelancers who had skills my team didn’t, spoke languages we couldn’t, and lived in lands we’d never traveled to. I’ve even spent time freelancing on my own for agencies, brands, and startups.

The advantages of collaborating with remote and independent workers are innumerable — access to better talent, more diverse perspectives, and niche subject matter experts are just a few. But, for those who come from a work environment where “freelance” is often synonymous with “temp” or “helper,” the idea of outsourcing meaty tasks to contractors can still seem risky despite the potential cost and creative benefits.


Where did this fear come from?

Although startups commonly use project-based teams to handle critical tasks without distracting core employees from bigger challenges, many brand and agency decision makers I encounter are held back by what I like to call “The One Time” complex.

The One Time it didn’t work out... The One Time someone went AWOL… The One Time they interviewed well, but didn’t deliver the quality we expected. Or maybe it was The One Time we needed to invest so much time getting our new worker up to speed that it would’ve been quicker to complete the work ourselves.

Everyone has an anecdote about the downside of outsourcing. The fear is often rooted in reality, but we’re at a point where smart businesses can no longer afford to be scared.

The growing freelance workforce is real, and it’s not just because of Uber drivers and Task Rabbits. Research shows that 66% of the 54 million Americans who freelance are skilled professionals or entrepreneurs who work on a project basis. And with more flexibility-seeking millennials choosing to abandon their full-time gigs, it’s predicted that independent workers will account for half of the talent pool by 2020.

Instead of being held back by The One Time things failed, we need to acknowledge the common denominator from our collective tales of failure — no reliable middle-man to manage freelancers, oversee budgets, and keep things on schedule.


Are producers key to the outsourcing equation?

In Adam Davidson’s NY Times piece, What Hollywood Can Teach Us About the Future of Work, he paints a mystical, magical picture of the model Hollywood has used to tackle entertainment for decades. “A project is identified; a team is assembled; it works together for precisely as long as is needed to complete the task; then the team disbands.”

In witnessing the efficient collaboration between contractors with varying skill sets, Davidson reflects,

“Why was this process so smooth? The team had never worked together before, and the scenes they were shooting that day required many different complex tasks to happen in harmony … They just got to work, and somehow it all fit together.”

Perhaps the real secret behind this seemingly magical “harmony” is the industry’s incredibly well-defined process for managing ad-hoc teams. His article only mentions producers once, in passing, but I’ve got a hunch that they’re the ones we can thank for “fitting it all together.”

So why aren’t all brands and agencies embracing the same project-based approach with gusto? It’s likely that project managers and producers at these companies already have enough on their plate. Especially as the digital age introduces more competitors and puts pressure on marketers to quickly deliver “relevant and timely” campaigns, the day-to-day management of in-house activities can eat up a lot of bandwidth. Having time left to strategically prioritize goals, create staffing plans, recruit specialized talent, and properly immerse new team members would be a luxury. And it’s these activities that–if given the proper attention–can ultimately increase profit margins and yield higher quality results.


Here’s why a centralized management role could make the freelance economy easier to embrace:

  1. Mitigate risk when your freelancer is unpredictably under-qualified

Most of the “failure” stories I’ve heard stem from issues working with agencies or recruiters that scout less experienced talent. Sure, they can usually find someone for your project in a pinch, but once you’ve factored their hourly markup into your budget, you may be getting someone more junior than you’ve bargained for.

If you don’t have the bandwidth necessary to oversee your new hire, it could be risky to assume that they’ll be senior enough to plan their time appropriately or know which questions to ask at the onset of a project. A dedicated manager can mitigate this risk by recognizing red flags early on and making sure your freelancer has the resources and feedback they need to finish a task properly.

2. Tech solutions for outsourcing still require a human element

Even with a growing number of digital platforms like UpWork and Freelancer connecting employers to low-cost freelance talent, it still takes manpower to break down your big idea into bite-size tasks, think carefully about the cause and effect of each phase, and craft job descriptions to attract the right talent for each assignment.

And assuming each task is correctly parceled out to its respective digitally-recruited “expert,” it’s very likely that your freelancers will be completely siloed from one another. Without a dedicated manager, communication issues can arise, and variations in the tone and quality of work could reflect poorly on your brand.

3. Avoid miscommunication between clients, strategists, and creatives

Often an undervalued skill, translating briefs between left- and right-sided brains can play a huge role in whether or not a project is successful. As the central point of communication for many multi-disciplinary teams, project managers can have a broader perspective and be crucial to quality control when outsourcing work.

While it’s not uncommon for a creative director or strategy lead to manage freelance teams directly, having them bear the burden of nuanced project details can present challenges and prove to be a poor use of their time and resources.

4. “Learn, iterate, and repeat” to refine your outsourcing approach

Effectively utilizing freelance teams can be a complicated process, and that process will vary from business to business depending on its size, capabilities, budgets, and goals. Something that works well for a team focused on tight-turnaround content marketing might not work well for one focused on longer-lead software development.

A manager that’s responsible for measuring the return on each engagement with an independent contractor will have more information to guide future outsourcing decisions. As they dedicate time to building relationships with talent and identifying opportunities to make your approach more efficient, your company can quickly improve its ability to get more done for less.

5. Create new in-house “pop-up” departments to grow your business

A freelance-savvy manager could make it incredibly simple for your company to handle things in-house that it never has before. Brands often abandon great ideas because they don’t have the right talent or bandwidth to pull something off. Similarly, agencies leave a lot of money on the table when they turn down opportunities to provide new services to clients, or they sub-contract work to other agencies with high overhead.


Especially as the lines between technology, advertising, and entertainment continue to blur, managers who expertly curate on-demand, project-based teams could be your secret weapon for staying competitive and bringing in more revenue.

Just as Hollywood producers can make high-frequency contract negotiation look like a breeze, so too can partnering with skilled freelance managers exponentially scale your own team’s ability to take on more work, try new things, and cross off the “maybe-some-day” items on your to-do list. If it works for $200M movie projects, it can probably work for your $50k branded content project as well.

Once we can collectively acknowledge where things went wrong with previous freelance encounters, we should feel confident that trying again with more structure in place can make the future of work simpler for both employers and independent workers alike.


Anjelica Triola is the Co-Founder of Skill Committee and an avid supporter of independent workers.

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