Many used to think freelancing was just for journalists and hitmen. Now, project-based, temporary contracts permeate many professions. In fact, according to Forbes, up to 50% of the U.S. workforce could be involved in freelance work by 2020. Not surprisingly, technology has made it easier to work with professionals across the globe, workers crave greater freedom and flexibility, and uncertainty makes job security less likely. These factors, and others, have contributed to creating an economy where "gigs" are now available to people in an increasing number of industries and with different skill sets. This includes:

  • Professional services: writing, marketing, accounting, and other white collar skills
  • E-lancing: Online-only freelancer or virtual assistant
  • Seasonal manual labor
  • Variable hour staffing: event-based labor pool
  • Independent contracting: providing goods or services to another entity under terms specified in a contract or within a verbal agreement
  • Talent: Actor, musician, dancer, singer, brand ambassador, host/emcee
  • App-based gigs: Driver, concierge, personal shopper, handyman, etc.

While the emerging gig economy has a lot of promise, both employers and workers still struggle with making the new relationship work.

YPO member Jessica Stackpoole knows how challenging it can be to create functional gig-based relationships. For decades, she has experienced the joys and frustrations of freelancing from both sides of the table.

At 25, Stackpoole was managing a large-scale experiential marketing tour. She was a freelancer managing freelancers and saw the difficulties of making short-term employment work for both her clients and her staff. It soon became her goal to deliver world-class brand experiences with people, for people.

Consequently, in 1999, she founded EventPro Strategies, a leading experiential marketing event staffing agency. This year, EPS will provide around 10,000 variable-hour W-2 employees throughout the U.S. and Canada for hundreds of Fortune 1000 brands and global marketing agencies. Through years of experience and relationship building, she has learned how to make gig work a win-win for all parties. Here are her tips for both employers and workers.

1. Know where and how to meet your match.

As in dating, the first step is knowing where to find an abundance of the people who make good partners for you--as determined by values, common interests, and similar outlook.

  • Employers should put a process in place to vet your candidates. Stackpoole explains: "EPS is responsible for booking the right people in the right roles for every marketing event we execute. To do so, we embrace technology throughout the vetting process, as most of the modern gig economy is virtual. We utilize several methods, including video resumes, Skype/Facetime interviews, and virtual meetings." She knows that some candidates misrepresent their skills and experience, and an agency can help mediate that risk. Otherwise, be clear on your expectations and look for a personality fit, as you would with a regular employee.
  • Workers should explore as many agencies, temporary work sites, and job boards as you can find. They will not all be equal for your needs. Register with multiple companies and keep your online profile and personal information/resume updated. Stackpoole also reminds, "Before registering or accepting an offer, ensure the company has been in business for a good amount of time and that the opportunity is legitimate. Vetting doesn't just happen on the employer side - freelancers should also investigate each company and opportunity."

2. Do the diligence that your partner is due.

Stackpoole also stresses the importance of looking out for your partner's best interests as well as your own.

  • Employers should stay current on U.S. Department of Labor employment classifications and compliance laws. "Employers often think that hiring temporary workers is simple, easy, and just needs a 1099 in every case. That's a myth," warns Stackpoole. Depending on the work and the professional relationship, some must be classified as W-2 employees. Misclassifying workers can result in significant liability and fines, and so can neglecting the labor and insurance laws of the places where your workers live. Staying informed, however, shows that protecting all of your employees matters to you.
  • Workers should also know their legal responsibilities. "When you are hired, see your commitments through," she advises. "While it is smart to build a pipeline and apply for several opportunities until your calendar is full, never quit projects before they are completed, even if you get a better offer. Burning bridges will haunt you in the long run." It may also open you, or your clients, up to any number of problems if you do not complete each contract to the best of your ability.

3. Commit to a responsive relationship.

Good communication brings understanding and efficiency, Stackpoole believes. Unfortunately, both short-term and distance work create many opportunities for neglect on both sides.

  • Employers should not forget that freelance professionals, like permanent staff, benefit from communication and supervision. "Do not assume they can just take the ball and run with it. Whether virtual or in-person practice active management," she advises. Deadlines, timelines, and milestones are often more, not less important, especially if the gig relationship is virtual. "Build checks and balances into your processes, gather data, and use that information to continually improve. At EPS, we live by the motto 'if it moves, measure it.' "
  • Workers should live by rapid response to hold up their end of the bargain. Stackpoole suggests, "Overcommunicate with the hiring company, from the first time you apply for the gig to the time you receive payment. Be very responsive and reply quickly to inquiries and requests. Be early. Make sure you can properly manage your calendar between multiple gigs and meet or beat all deadlines. Proactively communicate if there are any delays or issues." Employers will often forgive if you encounter occasional delays or obstacles, as they experience those themselves. They are more comfortable with challenges than silence or vague excuses, however.

4. Put contingencies in place.

There are decades of precedent in place for adapting to unexpected circumstances in a traditional workplace. The relative newness of the gig economy means there is less contingency experience on both sides, so everyone must take a proactive, creative, and responsible approach.

  • Employers and Workers alike should expect the unexpected and plan to protect both themselves and each other. Stackpoole insists, "It's healthy to be naturally paranoid and always have a Plan B (and even a Plan C). Cars break down. People anywhere get sick, or run late, or experience other problems, even when they work virtually or on a temporary basis." Gig workers should know in advance what they will do if they find themselves unable to complete a contract for a client. Employers should also behave as though the best defense is a good offense by hiring well in advance of their deadlines when possible. "Waiting until the last minute to find help generally takes more time and effort, as most great freelance workers are booked well in advance. And even if someone is available, quick turn pay rates are often much higher." If a pinch hitter or crisis specialist makes room in their calendar for you, don't disrespect their efforts by nickel-and-diming or demanding unexpected add-ons.

5. Be the partner they want and need.

Stackpoole reminds both parties that the most basic rule hasn't changed: in every sector, the good and noble employer/employee ride off into the sunset together. Poor talent and clients also tend up to wind up in the relationships they deserve.

  • Employers should keep in mind that the gig economy is like other sectors: "It is competitive when it comes to securing and keeping top talent coming back. Offer industry-standard rates and always pay on-time. Treat temporary workers as though they are a part of your internal team. Once you find them, you will want to keep the right people engaged, happy, and feeling rewarded. Even small gestures like public recognition, first right of refusal for new projects, freelancer of the month awards, and more, are extremely effective." Freelancers do talk to each other, and word gets around about good and bad clients.
  • Workers should understand: "In the gig economy, repeat hiring and referrals are key to your success." Experienced freelancers know that they must compete with many others--sometimes from all over the world--for a limited number of opportunities. Those who show passionate engagement with their partners will have an edge. "Focus on exceeding expectations - remember that there is only 1-degree difference between hot water and boiling water. Sometimes the little things you do add up to take you from good to great. When starting out, consider taking the jobs that are more challenging for the hiring company to fill. These might be farther away, slightly lower-paying, or less sexy. By exceeding expectations in that environment, you will become a hiring manager's go-to person. 'Saving the day' for a company will lead to better, and oftentimes exclusive, opportunities down the line." Employers will almost always prefer to work with a known, and respected, quantity than taking a risk on someone new and unfamiliar.

Each week Kevin explores exclusive stories inside YPO, the world's premiere peer-to-peer organization for chief executives, eligible at age 45 or younger.