Onboarding Freelancers Is Tough -- Here's How to Do It Right the First Time

Maximize the value of your freelance partnerships by treating freelancers like a part of the team.
Onboarding Freelancers Is Tough -- Here's How to Do It Right the First Time
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Guest Writer
CEO of Paro
7 min read
Opinions expressed by Entrepreneur contributors are their own.

Almost a third of American adults are engaging in some form of gig work, according to recent Federal Reserve stats. This includes everything from freelance accounting to driving for Uber.

While many gig workers serve people directly by delivering food or providing transportation, an increasing number of freelancers target their services toward businesses. Companies are outsourcing work at historic rates, and independent contractors have the skills, experience and availability to meet any company need at the drop of a hat. It’s a match made in heaven.

Unfortunately, working with freelancers isn’t always straightforward. Some business owners expect freelancers to jump in and fix their problems immediately, but they fail to provide the context, information and documentation necessary to facilitate such improvements. To make the most of freelancer agreements, business leaders must provide their contract workers with the resources they need and the respect they deserve.

Busting the ‘freelancers aren't meeting company expectations’ myth.

In my experience, the myth that freelancers don't meet companies' expectations is only prevalent in companies that haven't yet given freelancers a shot. Freelancers essentially run their own businesses, and those businesses rely on repeat clients. That means freelancers tend to strive to do their very best work in order to maintain relationships with clients.

To maximize this potential, though, there are a few things to understand from the start. Too often, freelancers take the blame for not meeting expectations. In reality, companies and employers can take action to bust this myth.

Related: 6 Tips for Getting the Most Value From Your Freelancer

It's critical to have a complete process during which employers and freelancers can set expectations and exchange information before working together. Business owners who assume that freelancers understand their unique needs force those freelancers to make assumptions of their own, many of which might not be accurate. Gathering the necessary data to make the most of a freelancer’s work might seem inconvenient now, but the better the foundation, the better the results.

Some business owners claim to have solved the problem by giving freelancers access to information. However, having access to something is not the same as actually possessing it. Freelancers don’t know the context or history of the company or its operations -- that’s why they need their clients to be as specific as possible during the beginning stages of the relationship.

Communication expectations can put a damper on freelancer relations, too. Some companies want daily updates. Others don’t want to hear about a project until it’s complete. Different communication frequencies are to be expected, but companies must communicate those preferences if they want to be good partners. Freelancers are not mind readers.

Communication rules also include the format. Should freelancers email progress reports? Plan for weekly calls? Message in Slack? In a study from The Economist, 34 percent of respondents named “unclear responsibilities” as a cause of poor communication. Clearer expectations lead to better results. The idea that a person who needs information should find it alone doesn't hold water when freelancers join the team.

Related: 5 Ways to Effectively Communicate With Employees

It’s not them. It’s you.

Sadly, many companies don’t even know what they need from their contract workers. By asking freelancers to discover both the need and the solution, businesses frustrate these workers and hamstring potential gains.

HR and legal departments often throw unnecessary wrenches into the works, too. These functions exist to protect businesses, but that responsibility can blind them to the potential benefits of partnerships. In a freelance economy, where speed is of the essence, bottlenecks can cause communication breakdowns and pushed -- or even missed -- deadlines. Don't spend too much time finalizing contracts or making freelancers jump through hoops before projects can begin.

These departments know that freelancers are the future, though. Research from PwC found that 46 percent of HR professionals expect the workforces at their companies to be made up of at least 20 percent freelancers or temp workers by 2022. If companies want to be ready for the future, they must reevaluate what it means to work with outside talent.

Take these four steps to make the most of freelancer partnerships:

1. Give the right people a heads up.

When freelancers will soon be joining the team, notify all the people who might need to work with them both in person and in writing. Dynamic Signal found that 33 percent of workers have considered quitting because of poor communication. Talk about upcoming partnerships to reduce that concern.

Clearly communicate why the company needs freelancers, how internal employees should expect to collaborate with them and what the desired outcome of projects should be. This eliminates countless hours that would otherwise be wasted on misunderstandings and duplicated efforts.

2. Host a kickoff meeting with all stakeholders.

Emails aren’t enough. Hold an initial meeting dedicated solely to the establishment of communication preferences, logistics and expectations. This shows all parties the importance of communication and forces stakeholders to talk through their needs. One of our freelancers suggested holding this short meeting separately to ensure we weren't trying to squeeze it in at the end of a strategy session, and it has revolutionized our efficiency when working with outside parties.

And we're not alone in this experience. Research from Vanessa Bohns and Mahdi Roghanizad, discussed in Harvard Business Review, found that in-person communication is 34 times more successful than email. And if your team is distributed across the globe, Chess.com co-founder Erik Allebest has discovered that introducing freelancers to the team via video chat is integral to fostering connections among team members.

3. Prepare a road map to gather information.

Ask freelancers about what kind of information they will need, and then connect them with the names and contact information of the people who can provide it. A cheat sheet of go-to experts can dramatically reduce processing time. Remember to give these people notice that a freelancer might call upon them.

Current employees are just as frustrated by failed onboarding as freelancers. Only 12 percent of respondents to a Gallup poll strongly agreed that their companies did a great job of onboarding. Great onboarding includes connections, not just data, so don’t skimp on the introductions.

Related: The How-To: Managing Freelancers Effectively

4. Give and solicit feedback on a recurring schedule.

Regular employees receive regular feedback. Why shouldn’t freelancers? Even if they only work on projects for short periods of time, they are valuable members of the team and are in a prime position to help the business learn and grow.

Great partnerships require input from both parties. Encourage freelancers to ask questions and be open with their answers. When freelancers submit work, be specific about criticisms and praises. Show contract workers that they belong on the squad to make the most of their talents.

The above Gallup report found that only 20 percent of employees believe that they receive performance management that encourages outstanding work. Break the cycle by treating freelancers with respect, and they will respond with higher-quality work.

Onboarding freelancers doesn’t need to be a complex, challenging process. By making simple preparations and treating freelancers like a part of the team, businesses can get more from contract workers and help both sides maximize the value of the partnership. Use these tips with your next freelance hire to see just how impactful the relationship can be.

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