Competing with a freelance workforce is already a reality for most organizations - it definitely is at my company, Mindflash. Roughly 20 percent of my team are freelancers. Across the US, 34 percent of the total workforce is classified as freelance today and by 2020 that number is projected to top 50 percent.

As the requirement to compete using freelance talent becomes the norm, the demand for the freelancers with the strongest skill sets will skyrocket. As that demand increases, so does the opportunity for freelancers to be selective about who they choose to work with. Organizations that don't carefully train their managers and architect their processes and technology to succeed in this New Work Future will face new ways to fail.

Here are three ways to fail in the freelance economy:

FAIL #1: No Context.

The sink or swim mentality that many organizations euphemistically label their 'fast paced culture' is a particular disaster for freelancers. Hiring managers bringing a full-time employee into HQ may get away without providing vital contextual information about how her work supports the organization's goals and mission, the formal and informal networks she'll need to navigate, etc. With a HQ employee, the manager's poor communication can be compensated for by multiple in-office experiences and interactions from which she can glean context. However, since freelancers are often working remotely, they are often entirely reliant on the hiring manager to provide the context that is vital for their success.

How can a hiring manager successfully onboard a freelancer? First, use the specifics of the freelance project you're hiring for as a roadmap for onboarding and training. Make sure they have the necessary "hard knowledge and tools" like training on company history, processes and access to key systems they'll be using. This can typically be accomplished with an online course, or maybe a conference call with screen-sharing. We recently created a short course covering the history of our performance on a key business metrics for the freelance Data Scientist we just hired, for example.

Also make sure you help them to acquire the "soft skills" also important in their day-to-day decision making. Here, a personal or video chat meeting is typically more successful in conveying your company's brand, mission, vision and culture. Most importantly, share why their project matters. What really motivates people in the knowledge economy, especially freelancers with an entrepreneurial mindset, is not a paycheck but the internal motivations of purpose and progress.

Technology can increase your odds of freelancer success. Research on adult learning, appropriately called The Forgetting Curve, tells us people forget 98% of what they learn within 30 days . So it's not enough to train once on hard and soft skills and be done. Find effective, remote communication tools like Skype, GoToMeeting or JoinMe, or a cloud-based Learning Management System (LMS) that can help you deliver and even automate your initial and refresher training in small, frequent bursts over the first weeks or months of a freelancer's engagement with your organization.

Fail #2: The One and Done.

Assuming you hired a great fit, you invested time and resources into training them on the hard and soft skills required by the project. If the project was a raging success, why wouldn't you try to extend the relationship and leverage that "first-project" investment across several more?

If giving them more, identical projects is an option, terrific. But even if you've "just" found a freelancer with effective soft skills such as discipline, accountability, communication -- please recognize that you've got a real asset. These are skills that are very hard to teach. Consider investing in developing some adjacent, hard skills that might allow that freelancer to tackle a similar but not identical project to optimize your initial investment.

For example, assume you employ a great freelance writer for your blog. She gets your brand, voice, and audience. She always delivers great work and on time. If you were then considering rewriting your website copy, you might consider cross-training her in writing for conversion. In my opinion, it's a worthy investment. Start with an assessment or pilot project to identify areas for required upskilling. Offer to pay for a publically available course, and/or provide small bursts of company-proprietary training to ensure she's getting the technical skills she needs. If you're successful, you'll be improving your business efficiency and providing a valuable way for freelancers to strengthen skills and expertise; something 72% of Millennials and 62% of Gen X prioritize.

Fail #3: Horrible Bosses.

It's not just a funny movie. According to Gallup, only 1 in 10 managers have a natural ability to lead--everyone else is killing employee engagement and needs some significant leadership training. If most managers lack the skills to properly lead full time employees--imagine the challenge of keeping a remote freelancer engaged and motivated.

Continue to strengthen your own employee's management skills through short bursts of training and engineered opportunities to communicate. Train them in technology that allows for the right frequency, medium and tone to keep freelancers engaged, clear about their goals and aware of how their contributions are making an impact on the organization's progress. Train managers to improve the quality of their communications via multiple mediums. Video chats have proven very effective for us, and I highly recommended them. I recently decided not to hire someone with otherwise stellar credentials because I could see over a FaceTime call that he was much more passionate about another type of work. I don't know that I would have gotten to that insight over email until it was too late.

In the future, half of our people will be freelancers and we'll need them to be awesome contributors. Expert freelance talent will be in high demand and they won't need to tolerate bad managers, messy onboarding, slow training, or stagnant career growth. Instead they will choose as clients companies that provide opportunities for them to strengthen their own skills while delivering "resume-worthy" results. The organizations that will win in this Freelance Nation will adapt their training and other people management efforts to grow from being an employer of choice to becoming a client of choice.

Published on: Oct 5, 2015