Digital Transformation

This Freelancer Onboarding Checklist Will Help Your Company

Encouraging any group of employees to march in step is difficult. The process gets even harder if some team members are only present part of the time.

In 2019, many companies in marketing, media, or communications now rely on freelance contributors. The gig economy may appear to be the way of the future, but brands don’t always know how to effectively integrate these new teammates.

Whether you’re looking to find new talent or already have external contributors helping out, you’ll benefit from a freelancer onboarding system. Think of it this way, providing freelancers the right resources will help them create better work and ultimately make your job easier. To help you along the way, I’ve compiled a six-step checklist that covers what to include.

1. Explain the company and business objectives

Full-time employees have a tendency to take brand messaging for granted. They’re around it so often that they eventually forget how it comes off to the outside world. When you work with freelancers, you can’t assume they’ll instantly know the nuances of your business. The first step you should take is educating them on these core details.

Marketers typically think about lobbing their pitch at prospective clients, but the same exercise could help you here. To create and maintain a productive relationship, you need to be clear about what the company sells, who it wants to reach, and how it wants to accomplish its business goals.

You can repurpose existing HR content—brand videos, welcome packets, training quizzes, FAQs—to get freelancers thinking the way you do. But keep in mind, you should pay freelancers for this time. That means once you’ve agreed to work with them, onboarding content should be clear, updated, and specific.

2. Introduce the team and technology

Be thoughtful about how you introduce freelancers to full-timers. Just because they won’t physically be in the office doesn’t mean you should rattle off names of people on a group email.

If you anticipate freelancers working repeatedly with full-timers, set up brief one-on-one calls between those individuals. Tell your freelancers exactly how often they’re expected to use your team as a resource.

As for tech, err on the side of caution and get your freelancers comfortable with every platform your team uses. At Contently, we use our own platform, Asana, Buffer, Tweetdeck, WordPress, and more to create and manage content. If you expect freelancers to turn in work on a particular platform, teaching them will benefit everyone. If they’ve never used a piece of software before or they need a refresh, hop on a screenshare call and walk them through it.

3. Set rules for communication

Before you hire any freelance creators, decide on a system that includes how you’re going to communicate with them.

One option is to divide your freelancer team into tiers. I’m on several editors’ email lists when they blast out their editorial calendars, but others just Gchat me questions about my availability. A couple simply forward me press releases and offers for interviews, and I can choose whether to bite or not.

Of course, there’s also the question of instant messaging and communicating with your full-time creators. In some cases, brands give full Slack privileges to freelancers. In other cases, the part-time creators were confined to certain channels. Either way, I’ve seen enough evidence to know that it’s helpful when freelancers join company culture. They pick up on brand messaging faster if they can see internal discussions.

4. Style guide and pitch guide

What’s your stance on the Oxford comma? Are there any words or phrases that employees can’t use? Do visual assets need to include certain colors? Sending a style guide to freelancers will give them answers to all the little creative questions that you already know in the back of your head. As your brand evolves, you should also update it occasionally, answering any new inquiries from freelancers.

Along with the style guide, you should also send your freelancers a pitch or brief guide, which can live as a PDF, Powerpoint deck, or Google doc. Format doesn’t matter as much as content. A freelancer can’t pitch you ideas effectively without knowing at a high-level what you’re looking for. Do you want to know intended sources ahead of time, or are you more interested in a tight theme? Do you want pitches delivered to you the same day each week, via email, or do you accept them on a rolling basis?

Tell them exactly how you prefer to be pitched, including the communication channel they should use and the structure their pitches should take.

5. Gather a portfolio of past success

There are a ton of reasons to file your biggest successes together, but freelancer onboarding is one of the biggest. If you tell 10 new freelance hires to “read the archives,” expect maybe two or three to walk away with the same vision you have in your head.

On the other hand, if you have a directory of standout articles, infographics, and case studies to choose from, they’ll have an easier time seeing things your way. If, for instance, you’re asking them to write a new version of a piece of content that always works for you, show them the original! Tell them why it worked, what you’d like them to repurpose, and where you’d like them to add in new material.

6. Ask for feedback

You’ll notice that a lot of my advice here stems from personal experiences as a freelance writer, staff reporter, and editor. That’s because healthy communication and freelancer onboarding comes from valuing both sides of the relationship.

Routinely interview your freelancers the way you interview your clients and seek feedback from full-timers. If you’ve been working with a freelancer for a few months, ask them to reflect on the onboarding process. Did they understand the brand when they began? What do they know now that they wish you had told them back then? The goal here is to internalize feedback and adjust your system to better serve freelancers who join in the future.

The gig economy has generally sent some office culture mainstays the way of the dodo. It’s still extremely rare to invest in post-mortem conversations with freelancers when a project ends. And when they part ways with a brand, they’re not often invited into exit interviews. But the more you embed freelancers into your company, the better their output will align with your brand’s values.

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