How to Onboard Freelancers & Independent Contractors

As an agency owner, you know how to build an agency team—at least one that consits of in-house members. Sometimes, though, you need external help. In such a case, many agencies leverage the flexibility of working with freelancers and independent contractors to fulfil their workload. To ensure that everything goes smoothly, agency owners should be onboarding freelancers via a pre-defined.

Traditional agencies have always relied on freelancers and contractors to help with variable service fulfillment. While they usually work on retainers, a newly onboarded client can quickly exhaust all available resources of the internal team—a perfect time to ask freelancers to join the agency, and streamline your operations.

At the other end of the spectrum are productized agencies which offer services that can be purchased right away. No calls, no waiting period—just purchase the service you need, and the agency starts work. Especially in its early stages, productized agencies rely heavily on project-based deliverables, as they don’t have the revenue to hire freelancers full-time.

One thing is the same for both types of agencies: every freelancer should enjoy an onboarding experience that introduces them to your workflow as quickly as possible.

In the following guide, I’ll introduce you to common mistakes agencies make when they set up their freelance onboarding program, what defines great process, and a step-by-step guide detailing how to onboard your new team.

Understanding how external team members think

When it comes to partnering up with freelancers, for most of them, you’re a part of their pool of providers that send them work. Most of them work with 2–3 agencies to be able to generate enough monthly income; some work only on a per-project or hourly basis.

Make sure that both parties enter an agreement that works for everyone. Why onboard a freelancer looking for a one-time gig if you need someone you can provide work for indefinitely?

To better understand freelancers, let’s look at the first ever published European freelancer survey. Almost half of them (45.7%) expressed issues with their fluctuating income. If you’re upfront about having steady work, that puts you in an advantage position of securing a long-term partnership.

One thing that has not been detailed in the report is that many freelancers work independently on their own terms. Speaking from my own experience, many agencies don’t fully integrate freelancers unless they work in the same capacity as a part-time employee. Their thought process: if you only work for ten hours per week, but I need to pay for your own access to Slack, Gmail, and other tools, it quickly adds up.

Well, that might be true, but think about it long-term. Would you rather check your email inbox for an urgent message, or get notified in Slack? Is it quicker to set up an automation in Zapier that notifies freelancers about things they need to know about via SMS, or invite them to a Slack channel? Don’t try to save money when there’s little benefit to it.

With that said, let’s look at a few more mistakes agencies make when it comes to onboarding.

Avoid these 3 mistakes with your freelancer onboarding

Hiring and retaining talent (especially when it’s remote and not 100% loyal to your company) can be a complicated experience for agency owners.

Not only does it take an incredible amount of time to find good people in the first place, but if you don’t have a good onboarding process in place, it can lead to a lot of issues.

Below you’ll find 3 big blunders when it comes to finding and onboarding freelancers for your agency.

1. Not having an onboarding checklist and documentation

Poor onboarding is often visible when freelancers are lost after they’ve gone through the onboarding system. They are lost, don’t know what to do next, and have trouble figuring things out on their own. Instead, they ask you the same questions over and over. Not great when your goal is to scale your agency.

Clear processes and procedures for tasks are a must, but here’s where most people go wrong:

• They either create a document and expect new joiners to magically find it, or

• They don’t provide instructions that correspond to the skill level they’re searching for.

Let’s assume that you’re looking for a project manager: this person should have different access rights to information than someone who will manage your email and calendar.

The latter doesn’t need the same level of detail when it comes to onboarding as the project manager, which is why onboarding should be based on roles.

Since you’re a busy business owner, adding leverage and building a document (instead of doing one-on-one training forever) is a no-brainer.

Having a thorough enough training allows you to:

• have freelancers start learning by themselves without taking time away from you or your team

• get freelancers indoctrinated on your team’s culture and how things work in your business

• make further training easier due to their already-learned material

If you don’t have these documents yet, start small and grow from there.

Training documents could start off being a one-page outline with a few bullet points, or a set of screenshots with step-by-step tutorials.

Consider assigning the task of keeping these up-to-date to someone in your team. And don’t forget to evaluate the alignment between the depth of the training and the quality of the result you want (or the skill level of the position you’re trying to hire for).

From my experience, it’s worthwhile investing early on in a proper wiki-style knowledge base software. Internally, we use Outline. It even allows you to share part of your knowledge base to the public. We use this feature for our developer-focused tutorials, as well as for internal purposes to document our app.

Our own clients also realized quickly how important good documentation is. In our interview with Rom from Podblade, he detailed how they’ve created an onboarding video for their partners. It introduces them to the client portal without their team having to do 1-on-1 demos every time.

2. Failing to set and meet expectations

I’m sure you’ve seen this happen with clients: if there’s a problem, it usually arises as a result of unrealistic client expectations.

The same thing can happen with employees or contractors. When things are not clear upfront and people start assuming due dates, compensations, or workload, things can get messy.

Here are just a few examples of how to avoid misunderstandings:

• If you’re working with outside parties from overseas, state clearly times and dates for communications and delivery (including the difference in timezones). If you work across different time zones, instant messaging will become async in most cases.

• Take note of questions that pop up frequently, and use documentation that was designed to share knowledge. A Google doc works in the beginning, but you’ll quickly realize that a searchable wiki is more efficient.

• If you’re paying on an hourly basis, ask how many hours it will take them to complete their work. Hourly work might make sense for agencies such as Johnathan’s web development agency, or editors in a content agency. A writer, however, should bill based on the content piece written.

• If applicable, ask for days and hours of availability, or preferred method of communications.

The fact that a freelancer works with agencies doesn’t mean they know what to expect from you. Every agency has different methods of working with external teams, o set your expectations upfront and prevent conflict.

3. Going for one full-stack freelancer instead of diversifying

Everything that’s entirely built upon one leg is bound to fall down: a business with one big client; a manufacturer with one primary supplier; an agency with only one full-stack freelancer.

Thinking that you can hire one person to do most of the things you need sounds great in theory. But especially with freelancers—where there’s really no explicit loyalty or commitment to your agency—you could end up having a hard time if they leave or are fully booked when you need them.

It’s always smart to have a few backups when it comes to talented contractors to outsource work to. Once your agency grows, think about hiring permanent employees, so you have a good mix between them and external help.

This isn’t always possible, but if you have the opportunity to do it, go for it. It can be of great help when business starts booming.

Freelancer onboarding checklist

Now that you know which mistakes to avoid when it comes to onboarding, let’s help you make them a part of your team step-by-step. Don’t expect freelancers to simply read a document and get cracking the next day, it’s a bit more complicated than that. The more detailed your brief and the clearer the scope of work is, the faster you’ll see results.

Let’s dive into onboarding best practices you should follow so you can make every new freelancer feel right at home.

Introduce freelancers to your company culture

In order to communicate more openly, let your new team members know about your company culture, who the founders are, what defines you, and what your business goals are. Freelancers understand that they are not a direct part of your agency, but they can help you shape its future.

If you provide them with documentation to get started, reserve one part about your agency so they know what to expect when working with you (and your team).

Set up the right communication channels

Slack, email, SMS, push-notifications—there are so many ways we can communicate these days. Sadly, some agencies still rely heavily on email chains, CC’ing everyone who needs to be informed. Imagine having to read an email thread containing 30 emails, but only one is relevant to you. Doesn’t sound like a good use of your time, does it?

If you decide to work with a developer, do they really need to be available eight hours a day? Developers prefer deep work, and need to focus on their tasks, without being disrupted by constant Slack private messages. The same might be applicable to content writers, who chip away at their tasks to meet their deadlines.

What I’m trying to say: when you set up communication channels, keep in mind that not everyone needs to be constantly available. Choose tools that help your agency be productive, without notifications getting in the way.

For instance, in SPP, your team has notifications tailored to their team roles. Someone who doesn’t have access to invoices doesn’t need to get notified about them. The cool thing is that there are in-app and browser notifications on top of email notifications. Your freelancers and employees can decide how they want to stay up-to-date with what’s happening.

Provide a style guide for contractors

Creative freelancers need to know what kind of rules you have when it comes to:

• tone of voice

• company branding

• communication dos and don’ts

This is especially important if you allow them to post about your company on social media, reach out to potential partners, and other tasks where they represent your agency. It shouldn’t be blatantly obvious that a third party is acting on your behalf.

The first step would be to set up a custom email inbox for your new team, and provide them with a branding cheat sheet that talks about your company, and things to keep in mind.

Ask employees to help with onboarding

Who knows your processes better than your employees? Well, you, but you’re a busy agency owner, so delegate the onboarding to your team instead. Sadly, the DIY mentality is very common among business owners.

With that said, there are many benefits to delegation. For instance, a project manager could give them an overview of your management systems, and other employees help them figure out how to work efficiently with other team members.

The great thing about involving your employees is that they can also answer questions remote freelancers might have. If those questions keep repeating, they might have to make changes to your onboarding process, or update existing documentation.

Be clear about invoices and NDAs

Nobody likes financial and administrative tasks, but they are a necessicty. Would you rather risk a lawsuit because you didn’t ask your freelancers to sign an NDA to deal with an important client? Or get in trouble with local authorities because you didn’t validate the VIES VAT ID of those invoices you received?

Before any work can commence, get these boring things out of the way. Tell freelancers exactly what needs to be on their invoices, and if they need to comply with certain security regulations (NDAs, computer encryption, use of VPNs, GDPR regulations, etc.). Some best practices should be mentioned in your agency’s documentation.

Keep in mind that the freelancers will also want to know when to invoice you, what requirements you have, and how you’ll pay them. In bigger agencies, a payment department will handle all the invoices.

Provide access to your data & tools

With the paperwork and theory out of the way, it’s time to start actual work. Invite freelancers into your client portal, give them access to your password manager, and let them know if they can request software that they need for their work. Some freelancers also need access to a dedicated email inbox, especially if they handle outreach in your company’s name.

Make sure to document who has access to what, and request signatures. This will make offboarding simpler if the freelancer is no longer working with your agency.

Lastly, help them make use of your project management software to reduce friction and errors. The sooner they are up to speed with the tool, the faster they can do their job.

Celebrate to make them part of the team

Now that the freelancer is finally on board, make them feel like they are really part of the team. Organize a small video call with everyone, give a shout-out in your Slack channel, or find other creative ways. Anything that shows them that they are not just another cog in your system will make them appreciate you for years to come.

Next steps after a comprehensive onboarding

Part of the onboarding process should be a feedback cycle. Ideally, freelancers will notify you if something is unclear, but if they don’t, ensure to follow up with them. Some are more reluctant to criticize you right away. After all, they are still getting to know your agency.

Assure them, though, that they can be open about anything, and shouldn’t be afreid to speak up. This is the only way you can improve your process and ensure that every freelancer’s onboarding is smooth.

Make new freelancers feel welcome

When there are so many things you need to take into consideration running an agency, it can be difficult to make freelancers feel as included as full-time employees.

That’s why it’s important to set up strategies that form a better connection right away, improve the way of communicating between internal teams and contractors, and allow for easy check-ins.