Freelancer Onboarding Best Practices: 6 Steps For Success

Supplementing your core team with freelancers is a great way to scale up your workforce; and, with the gig economy on the rise and more “digital nomads,” there’s great talent out there. But it’s not without its risks. You need to find someone who is the right fit and who has the experience and expertise you need. Then, you need to get them onboarded to your culture, team, and process so they’re productive as quickly as possible—all with no guarantee that they’ll stay with you beyond your first project together.

So, how do you onboard freelancers in a way that makes them feel part of the team—and hopefully want to stick around for a while? How do you decrease the time to productivity and ensure they are ready to perform?

At SweetRush, we have been successfully supplementing our core team with motivated and committed freelancers for 20 years—two decades of experience and lessons learned!

Here are our best practices for onboarding new freelance team members in a way that creates a seamless experience for both our team and clients.

Onboarding Best Practice #1: Use The Same Hiring And Onboarding Process For Both Freelancers And Employees

Like most companies, we have a rigorous screening and recruitment process to help us find competent, experienced, and values-aligned full-time team members.

And guess what? We use the same process to vet and hire our freelancers!

We also provide our freelancers with the exact same onboarding experience as our core team members. We do this for several reasons:

  • As a custom learning company, our projects can often take months rather than weeks. Freelancers, therefore, end up working alongside our core team and clients for an extended period. We want to ensure a mutual fit, and the best way to do that is by investing time in our recruitment and onboarding process.
  • Having a deep understanding of our culture and purpose makes it easier for freelancers to adapt their mindset as they transition from their—and their other clients’—way of working to ours.
  • A comprehensive onboarding experience creates accountability and offers performance improvement opportunities. When needed, we can refer back to the hiring and onboarding experience to provide feedback and coaching.

Onboarding Best Practice #2: Set Clear Expectations

One of the benefits of being a freelancer is being able to set your own schedule and work flexible hours. That might not necessarily line up with what you had in mind—particularly if you are operating in different time zones.

During the hiring and onboarding process, we discuss and set expectations for attending team and client calls, meeting deadlines, and having response times to email or instant messages—even the person’s ability to jump online for a quick huddle. Having these expectations clearly stated avoids any misunderstandings and subsequent impact on the client or team experience.

Onboarding Best Practice #3: Provide All-Access Passes

Nothing is more frustrating than starting a new position and not having access to the tools and resources you need to be productive.

Our freelancers have access to the same systems, tools, social platforms, and company activities as our full-time team members from day one. This includes a SweetRush email account as well as access to our calendars, drives, content management systems, and other productivity tools. We also sign freelancers up to our social platforms and extend invitations to join our in-house social networking, creative, and wellness groups—of which there are many at SweetRush!

Providing this access promotes a sense of community, inclusion, and belonging with the added bonus of avoiding bottlenecks and boosting efficiency and productivity. More importantly, it eliminates any potential for a “them and us” culture.

Onboarding Best Practice #4: Use Simulations To Teach Processes

We love to hire freelancers who are at the top of their game and bring a fresh perspective to solving our clients’ challenges. We actively encourage disruption, creativity, and innovation. The catch: With multiple team members working on multiple projects with multiple clients, we need some order and consistency in our process. And this can be a challenge for newcomers—particularly those who have worked very successfully on their own using a different process.

To help ease freelancers into our way of working, they complete a simulated project as part of their onboarding experience. For new learning experience designers (LXDs), this means working through a learning solution design from start to finish. The LXD completes the simulated project using the same tools, templates, timelines, and processes they’ll encounter on their first live project. And like a live project, they receive peer review, coaching, and feedback along the way.

This approach serves two purposes:

  • It provides team members with a safe space to practice, explore, and fail.
  • It sets expectations and removes the element of surprise—the first “live” project after onboarding doesn’t feel like a first project.

Freelancers appreciate the rigor of this onboarding process. They feel better prepared to succeed in their work versus being rushed into an assignment and being forced to sink or swim.

Onboarding Best Practice #5: Provide An Ongoing Support Network And Resources

If you’re onboarding remote freelancers, consider their experience. Along with the excitement and abundance of warm welcomes, there may also be a sense of isolation—after all, you can’t tap your cube mate on the shoulder to ask a question when there is no cube.

As an entirely remote company for more than a decade, we have developed a plethora of support and networking practices to help newcomers feel connected and supported. For example, newcomers to the LXD team are each assigned a coach who supports them through their first project, which, if you recall, can take weeks or months to complete. Adopting a proactive approach, the coach checks in with their newcomer on a regular basis—neatly avoiding every newcomer’s worry about “bothering people with silly questions.”

We also leverage technology. Our knowledge management system contains pages devoted to each team along with links to the various tools, systems, and templates they use. We use collaboration tools to set up project-specific channels as well as informal chat channels for different teams. Need help brainstorming a solution? Hop on the LXD team chat and see who’s available.

These warm welcomes aren’t limited to our in-house freelance teams. Pre-pandemic, when we placed freelancers to work at client locations as part of our staff augmentation service, we asked clients to set them up with a “lunch buddy” on their first day to improve their onboarding experience. (These days, of course, it’s a Zoom coffee chat!)

Onboarding Best Practice #6: Remember To Say Thank You!

Sometimes the onboarding journey ends with a freelancer not being allocated a project right away. Maybe the timing didn’t work out or a project got delayed.

In these instances, we like to thank our onboarders with a gift card as an appreciation of their time. After all, we want to work with them when the opportunity does arise. Plus, we are genuinely grateful for the time they have given us.

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We hope you’ve found these tips helpful! As the workplace environment continues to evolve, don’t forget to update your onboarding practices. And don’t forget about your freelancers.

If you are new to working with freelancers or have questions about staff augmentation or onboarding, find out more in our eBook Staff Augmentation for Learning and Development: The Agile Talent Solution for Modern Business.

Our job is to help you achieve your objectives and be successful. Engage us at any point, from analysis to custom development (including e-learning, mobile, gamification, and ILT) to evaluation.

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