Working with Freelancers: Tips for Hiring & Managing a Freelance Team

Small business owners are, by necessity, jacks-of-all-trades. Need more leads? You'll have to figure it out yourself. Confused about bookkeeping? It's time for some research. At some point, though, we all realize that it's time for outside help. We can't keep growing or scale our business without some assistance.

Hiring regular employees isn't straightforward either -- it comes with its challenges and often with a high price tag. That's why small business owners and solopreneurs like me turn to freelance talent. With freelancers’ help, small businesses can tap into expert skills, get help only when they need it, and thrive with a flexible workforce.

Like everything else, though, hiring and managing freelancers takes some preparation and skill. Lucky for you, I'm about to share the process I have used to successfully curate teams of freelancers that let me run a successful marketing business and still have time to play with my kids.

Hiring the right freelancer

Success with freelancers starts at the beginning: you have to get the right people onto your team. So how do you make good choices when it comes to hiring freelancers?

Define and communicate your needs

First, you need to figure out what you're looking for. Whether you’re hiring a content writer or a virtual assistant, get specific. You can get as specialized as you need with a team of freelancers -- you don't need to find generalists, since you can turn to different people for different tasks. 

When I'm hiring freelancers, my first step is to write a good job description. Answer these questions:

• What kind of work will they be doing?

• What are the key objectives for their work?

• How many hours per week do you expect to need their help?

• How much will it pay?

• What experience do they need to have?

Where to source freelancers

What’s the number one way to find skilled freelancers? Poach them from your friends and colleagues, of course!

OK, so we’re not actually talking about poaching talent... but definitely turn to your network first. Let people know that you’re looking for freelance help and ask if they have referrals. I’ve found that referrals are the easiest way to get quality freelance talent without a ton of effort. 

For this kind of thing, it’s best to throw out a broad request. Don’t just email a couple of friends. Referrals can come from contacts you didn’t even think to ask. Post your request for referrals to your social media networks. Who knows? That college friend you haven’t talked to in ten years might know the perfect graphic designer for your freelance team.

If you strike out with your network, it's time to post the job. I recommend starting with Upwork and LinkedIn. Remember to put in all the job details: experience, type of work, hours, and pay. Estimated hours and pay are crucial to include: you don’t want to find a perfect freelancer only to discover that they don’t have enough bandwidth to cover your project.

Check for fit with a paid trial project

The last step is to give your candidate a trial project. Even a great freelancer won’t be a fit for every project. Build in a buffer by offering candidates a paid trial project. 

Why pay for a test? Freelancers aren’t doing this work just for fun. They’re running a business, just like you. If you want professional work, expect to treat your freelancers like professionals. Professionals don’t work for free. By demonstrating your respect for their time and work upfront, you’ll find better quality freelancers.

Let your candidate know that you’re hoping to find someone for ongoing work and that this opportunity is a trial run. If the test assignment turns out great - awesome. You’ve just found a new freelancer! If not, no harm’s done. Move on to the next candidate.

Managing projects with a freelance team

Once you have the right freelancer, you still need to set up a way to get them working. The more preparation you put in here, the better. Preparation means fewer miscommunications, fewer revisions, and fewer headaches.

For me, preparation starts with the right tools.

Loom: Video training for onboarding new freelancers

Onboarding and training freelancers can be time-consuming, but there are ways to make it easier and more efficient. Here’s my favorite way to train someone else on one of my processes.

Using Loom, I record my screen while I walk through the process and explain each step. Then, I share a link to the Loom recording. Boom! On-demand video training is done in barely more time than it would take me to complete the process myself.

With video training, you don’t need to worry about getting calendars aligned for one-on-one training. If your freelancer needs a refresher, they can return to the recording. And if you need to onboard someone else? You’ve already got the training ready to go.

So, how do I share the Loom links? Trello!

Trello: Organize projects to stay on track

When I’m tracking work for many different clients and collaborating with a big team of freelancers, Trello makes it possible to stay organized. Here’s how I use my favorite Trello features when working with freelancers:

• Card Assignees & Due Dates: When I send an assignment to a freelancer, I assign them to the Trello card and set a due date. Even if that freelancer is working with me on separate projects for five clients (on five different Trello boards), they can see a dashboard of their assignments and deadlines.

• Checklists: For each project, I do a final quality and completeness check using a checklist on the Trello card. Rather than recreating this checklist over and over, I copy from an existing checklist. Each webinar I record has over 20 tasks! With this process, nothing gets forgotten and I’m not trying to remember each of the tiny tasks for every project.

(Already a Trello fan? You’ll appreciate this Gigantic List of Little Trello Tips.)

Hiring expert freelancers lets you scale your business

As a solopreneur myself, I know what a challenge it is to manage all the aspects of a business. By necessity, we have to develop skills in areas where we’re not experts. (Bookkeeping, anyone?) With the help of an amazing team of freelancers, you can grow your business. The advice above will help you get there.

But if you’re struggling with marketing and already strapped for time, you may not want to source and manage freelancers yourself. For each client I work with, I create a team of experienced freelancers. This isn’t a one-size-fits-all team: it’s curated to meet the needs of your project. If you’re ready to let go of your marketing challenges, schedule a consultation to learn about my flat-rate marketing director service.