Working With Freelancers: How to Set Your Workplace up for Success, Part 2

Working with Freelancers - Part 2

There are two sides to the freelancing puzzle: those hiring and working with freelancers, and those doing the freelancing. As with most puzzles, if the pieces aren’t meant to fit together, you can’t force it. To break it down a bit more, no two companies are the same, and no two freelancing relationships will be identical either.

As a longtime freelancer, I often feel the challenge of trying to understand and fit in with the culture of the team I’ve been hired to work with, all while doing my job to the best of my abilities. The flip side is when a company starts working with freelancers and has to determine how to create a work environment that supports existing staff while welcoming freelancers for a project or the long-term.

For some companies, freelancers can be similar to on-demand services. You keep a core team and then pad out your support players for specific projects or times of the year. If you’re considering hiring freelancers to support your existing team, there can be a learning curve. That said, once you realize the full benefits of working with freelancers, you’re probably going to wonder how you managed til now.

timeline for working with freelancers

The timeline of working with freelancers

Since there are many moving parts to even the most basic projects, you should come up with a plan for hiring freelancers rather than sending out a panicked request for backup. You’ll also have to manage expectations, including setting realistic timelines for each element of the engagement.

When Sarah Doheny, founder of YUBpr, launched her PR consultancy, she was adamant about strategic planning, especially when hiring and working with freelancers.

“… It is one of the most fundamental components to what we do as timelines and structure serve both parties,” Doheny said. Along the way, she realized that “sometimes timelines just don’t happen the way we hope they would for many reasons.”

She’s also noticed that, at times, clients become non-receptive suddenly which can throw off an entire project. For that reason and more, Doheny has come up with an informal three-month rule for new engagements when working with freelancers.

Start with a three-month plan

For longer-term projects, it’s important to set up a timeline that allows you to plan the work, get it done, edit or tweak, gain approval from supervisors, and then submit it to your client.  After years of trial and error, Doheny came up with her own plan for making the first three months of any engagement about learning, fixing, and getting to the business at hand.

“The first month is gathering information and digging into the client’s overall picture to create the vision,” Doheny said. But along the way she learned that things don’t always work as planned.

“Flexibility is key” along with touching base with the client before moving forward. By month three, you should be settled into some sort of a groove with both your freelancing team as well as your client.

Are you considering working with freelancers? Read the second part of our short series on working with freelancers. Spoiler alert: We set up a short timeline to help you figure out how long it should take. Read more via @rachelcw @clearvoice… Click To Tweet

sample timeline for working with freelancers

A sample timeline for hiring and working with freelancers

Since the amount of time you spend on each aspect of working with a new freelancer will depend on the job at hand, we’re offering a very loose timeline you can tailor to your own needs.

  • Week one: Decide internally what the needs are, the job requirements, budgets, and any benefits or incentives. This would be a good time to research the going rate for freelancing services in your industry.
  • Week two: Create the job description and set up parameters ranging from whether the freelancer deals with clients at all, to whether there are set deadlines per project.
  • Week three: Start the search for the best possible freelancer. Ask friends and colleagues and post job listings or gig alerts on your social media accounts. Depending on your industry, there will probably be specific hashtags to help you to amplify your search.
  • Weeks four and five: Interview prospective candidates. Figure out their place on your own team. Decide on your hire and inform your team. Work with HR and your attorneys on any contracts or work agreements needed.
  • Weeks six through eight: Provide your new freelancer with all materials needed to integrate their skills with your team. Pad timing for errors. Use this time to create a sample project if possible.
  • Weeks eight through 1o: Pay attention to the way deadlines are met, critique received, and feedback is given from other team members. After about a month on your team, you should have a clear idea if this freelancer is the right fit for your team, project, and client’s needs.
  • Weeks 11 and 12: Meet with your team and your freelance hires. Reviews projects completed and also best or worst results. Decide what happens next.

Bear in mind though, that your timeline might not be the best fit for a freelancer. Consider hiring or assigning a project manager to keep the workflow consistent.

Matt Villano has been a prolific freelance writer and editor for 25+ years. Villano said he wishes there was some sort of uniformity involved in setting up a freelancing timeline.

“Unfortunately, just like every person has their own eccentricities, so too does every client.” For that reason, Villano usually gives new clients three to six months while they try each other on for size. That also helps him see how flexible or demanding their deadlines usually are.”

After that point, if their styles don’t mesh, Villano will make the call whether to stick with the project and client or not. A self-admitted people pleaser, he said he’s “usually am willing to bend quite a bit before breaking.” Be open to tweaking your freelancing arrangement as it goes.

how to vet freelancers

How to vet freelancers

Now that you’ve decided to work with a freelancer (or a dozen!) how do you find them? And once you do find the freelancer of your dreams, how can you properly vet them?

Ask your network

Many freelancers rely on their networks and word-of-mouth recommendations. The hope is that if you know the person making a recommendation, you’re already ahead of the game. If you post an ad looking for freelancers, you can include very specific requirements to weed out any time-wasters. And while you’re at it, make sure to actually follow up, even if that means clicking through to see if someone’s portfolio is up to date, or following up with a reference, especially if something strikes you as being potentially sketchy.

Fine-tune your freelance needs wish list

Ilana Zalika, founder and CEO of Resound Marketing, said that when she’s looking to scale up a project or add someone with specific expertise or experience, she looks to freelancers. When choosing who to work with, Zalika said there are specific skills that help her decide who to hire. “Experience is key, but ultimately, communication and transparency are the most important qualities we look for in our freelancer relationships,” she said.

Having had freelancers join her team on both a temporary and longer contract basis, Zalika realized that it’s critical they work seamlessly and collaboratively with her in-house team. To ensure this, she does an in-depth onboarding meeting where clear expectations and touchpoints are set so that all involved parties are on the same page.

Be flexible

Much in the same way that being a freelancer offers a kind of flexibility being on staff might not, the hiring process tends to be less rigid as well. “We want to be respectful of a freelancer’s tried-and-true processes, but expect the same in return,” Zalika said. For her, that means working together to find a groove that ultimately works best for her clients — which usually means some adjusting on both sides.

“A big red flag would be someone who is not willing to be flexible or collaborative in that regard.” Zalika also expects freelancers she hires to fully understand the project and process. To that end, she said she’d be “wary of someone who doesn’t ask a lot of questions upfront. It’s the best way to ensure you’re getting a feel for the project and processes.”

Be absolutely clear about deliverables needed

Unlike staffers who are paid a regular salary no matter how long a project drags on, a freelancer has to be more mindful of their time and other clients. For that reason, it’s crucial to agree on all aspects of a project in advance. While it might seem annoying at the time, it helps prevent frustration. Longtime freelancer Aly Walansky said she can see warning bells with clients sometimes, particularly when they come back to her for things they never mentioned in the first place.

“It’s important to get clear instructions on deliverables because if what they are asking for changes or increases, the pay you are getting may need to be updated as well.”

Be fair

If you are considering hiring freelancers, pay fairly and if you’re able to, pay generously. Just because this might be the first time you’re working with this person, that doesn’t mean they haven’t been working within your industry for decades. When you treat a contract player with respect and appreciate their work, it’s entirely possible they’ll bring a little bit extra to the project as well. In this context, they may be working for you, but they also might know insider information or tricks of the trade that will help you in the long run. Bear in mind that working with freelancers involves a lot of give and take to produce the best consistent results.

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About the author

Rachel Weingarten

Rachel is an experienced freelance content creator, content strategist, writer and copywriter, and author of three award-winning nonfiction books. She specializes in business and style and the business of style.