Canada Association of Tourism Employees

Freelancer Onboarding Greatest Practices: 6 Steps For Success

Productive team players: onboarding freelancers

Adding freelancers to your core team is a great way to grow your workforce. And with the growing gig economy and more “digital nomads” there are great talents. But it’s not without its risks. You need to find someone who is a match for you and who has the experience and expertise that you need. Then you need to integrate them into your culture, team, and process to get them productive as quickly as possible – all with no guarantee that they will stay with you beyond your first project together.

So how do you involve freelancers in such a way that they feel part of the team – and hopefully want to stay a while longer? How can you reduce the time to productivity and make sure they are up and running?

For 20 years we at SweetRush have successfully complemented our core team with motivated and committed freelancers – 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 our clients.

Onboarding Best Practice # 1: Use the same hiring and onboarding process for freelancers and employees

Like most companies, we have a strict selection and hiring process that helps us find competent, experienced and value-oriented full-time team members.

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

We offer our freelancers 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 instead of weeks. Freelancers therefore work together with our core team and our customers over a longer period of time. We want to ensure a mutual match. The best way to achieve this is to invest time in our recruiting and onboarding process.
  • A deep understanding of our culture and purpose makes it easier for freelancers to adapt their way of thinking as they switch from the way they – and that of other clients – work to ours.
  • A comprehensive onboarding experience creates responsibility and offers opportunities to improve performance. If necessary, we can draw on the hiring and onboarding experience to provide feedback and coaching.

Onboarding Best Practice # 2: Set Clear Expectations

One of the advantages of being a freelancer is that you can set your own schedule and have flexible working hours. This may not necessarily be what you want, especially if you operate in different time zones.

During the hiring and onboarding process, we discuss and set expectations for participating in team and client meetings, meeting deadlines, and response times to emails or instant messages – even the person’s ability to do a short meeting online leap. If these expectations are clearly formulated, misunderstandings and the resulting effects on the customer or team experience are avoided.

Onboarding Best Practice # 3: Provide All-Access Passes

Nothing is more frustrating than starting a new role 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 register freelancers on our social platforms and invite them to join our internal social networks, creative and wellness groups – of which there are many at SweetRush!

Providing this access fosters community, inclusion, and belonging with the added benefit of avoiding bottlenecks and increasing efficiency and productivity. More importantly, it eliminates any potential for a “you 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 new perspective in solving our clients’ challenges. We actively promote disruption, creativity and innovation. The catch: Since several team members are working on several projects with several customers, we need a certain order and consistency in our process. And that can be a challenge for newcomers – especially for those who have worked very successfully alone with another method.

To make it easier for freelancers to get started with 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 with the same tools, templates, schedules, and processes you encounter on your first live project. And as with a live project, they receive peer review, coaching and feedback.

This approach serves two purposes:

  • It provides team members with a safe space to practice, explore, and fail.
  • It raises expectations and eliminates surprises – 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 be successful at their job than when they are pushed into a task and forced to sink or swim.

Onboarding Best Practice # 5: Provide an ongoing support network and resources

When engaging remote freelancers, consider their experience. In addition to the excitement and abundance of warm greetings, there can also be a feeling of isolation – after all, you can’t pat your Dicemate on the back to ask a question when there is no Dice around.

As a completely remote company, we have developed a variety of support and networking practices for more than a decade to help newcomers feel connected and supported. For example, newcomers to the LXD team each receive a coach to support them with their first project, which, if you remember, can take weeks or months to complete. With a proactive approach, the coach reports regularly to his newcomer, avoiding every newcomer worrying about “bothering people with stupid questions”.

We also use technology. Our knowledge management system has pages dedicated to each team, as well as 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. Do you need help with brainstorming a solution? Jump into LXD team chat and see who’s available.

These warm greetings are not limited to our in-house freelance teams. When we were placing freelancers at customer sites as part of our recruitment service prior to the pandemic, we asked our customers to put them together with a “lunch buddy” on day one to improve their onboarding experience. (It’s a zoom coffee chat these days, of course!)

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

Sometimes the onboarding journey ends with a freelancer not immediately being assigned a project. Maybe the timing wasn’t right or a project was delayed.

In these cases we would like to thank our onboarders with a gift card in recognition of their time. After all, we want to work with them when the opportunity presents itself. We are also really grateful for the time they gave us.

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

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

eBook Publication: SweetRush


Our job is to help you achieve your goals and be successful. Involve us at any time, from analysis to customer-specific development (including e-learning, mobile, gamification and ILT) to evaluation.

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