The Inside Track on Finding (and Keeping) Top Freelancers

Top freelancers often don’t need to look for new projects, the projects come to them. In fact, most freelancers (72 percent) say they have the amount of work that they want—if not more. This gives the freelance marketplace a balance of power that hiring managers don’t always consider: Freelancers don’t need to work on your project if they don’t want to.

Instead, they can pick and choose the projects they’re most interested in and the clients they most want to work with. The strength of your reputation, quality of your job post, and ability to collaborate once the project has started can all have a significant impact on your ability to find and keep top freelancers.

During a panel moderated by Singularity University during Upwork’s Work Without Limits New York Summit, three freelancers talked about how they screen potential clients:

Here’s a look at what they had to say…

Q: What’s the first thing you do when you’re invited to check out a new project?

Koeling: On the Upwork platform, you can see a business’s previous history with freelancers [on Upwork]. If they have a good background—they’ve clearly worked with the same freelancers over a long period of time—that’s a good sign. You can also go on LinkedIn to check out the background of the hiring manager.

Dekker: I start with research on both Upwork and Google. Obviously, I’ll Google the company and/or the person reaching out to me. What’s their track record on Upwork? Do they have any current ad campaigns running, and if so, how are they going? This will give our initial conversation more value.

Tapia: The first thing I look for is the skill set described in the job post. Is it a skill set that I have? And if so, what can I bring to the table to match it or go beyond? I want to make sure the project is a really good fit.

Q: What do you look for during an interview?

Dekker: I really see the interview as a two-way process. It isn’t just a company that’s interviewing me; I want to find clients I really enjoy working with, too. Some of the most important things I look for:

  • Do they have a team in place?
  • Do they have a vision that I can get behind?
  • Are my values aligned with their values?
  • Are we heading in the same direction?
  • Is this an opportunity for a long-term partnership?

I also look for potential red flags. One of the more common ones is a client who says they have a lot of side projects to send my way. You might think that sounds great, but in reality, it tells me they likely aren’t focused on what their mission is and what their directive is.

I want to work with someone who can show me, “Hey, we’re trying to build this thing—and just this one thing—and we’d love for you to be an integral part of that.” That’s really what I’m looking for in these initial conversations. From there, it can lead to discussing scope, timelines, and other details.

Q: What can clients do to help establish trust?

Tapia: A video call for your initial conversation is a good way to connect and read a potential client. It can also help to start with a small test project so the freelancer can show what they’re able to do and you—the client—can feel more comfortable hiring that freelancer.

Dekker: When a contract ends on Upwork, you have the ability to leave a public review about how you think I did. For example, if I shafted you for the last three months, you can leave a review that says, “Pep sucks, don’t hire him.” And then I’ve got to live with that zero star review on my profile. I have a reputation to uphold.

Q: How do you keep a strong relationship with a freelancer during and after a project?

Koeling: The relationship goes both ways. As a freelancer, I can go to multiple companies and be paid by multiple companies. My strong work ethic means I will provide the best work I am capable of to every client that I have. At the same time, I also have to trust that my clients aren’t going to look for other freelancers to take over my project.

Tapia: It says a lot if you already have a good relationship with each other. I think anyone would want to stay connected with someone they have a good relationship with. A new opportunity may come up, but I may not get the same sort of relationship; that’s definitely something I keep in mind.

Q: So how do you build that kind of relationship?

Dekker: The big one for me is talking to a client, in that first interview, about their lines of communication and what those expectations are. If they have a good team in place, you can recognize some of those feelings and conversations.

And we need to talk about boundaries: “Look, I’ve got a wife at home and I will not work outside of these set hours unless the whole Google ads is on fire and we need to turn off campaigns, or the landing page is down and we don’t want to spend $20k this weekend.” In those cases, I’m there. But most of the time, it’s setting those lines of communication up early on.

Koeling: It can depend on the company and how those internal processes meld with the processes I have for my own work. It’s important to have easy ways to communicate with each other.

The bottom line? Finding great freelancers is an investment—and it’s worth it

It takes planning, thoughtfulness, and consideration—on both sides—to engage a top freelancer. Not unlike the due diligence, you’d invest in hiring a new employee. But with care and attention to detail, you can attract the quality freelancers you’re looking for and build a long-term partnership that can help both of you succeed.

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