Talent Relationship Management: Tips for Working Well With Freelancers

If you've ever worked with a freelancer before, you've seen firsthand how these professionals can help your business thrive. But you may have only scraped the surface of the true value that a freelancer can bring to your organization.

To go one step further in your work with freelancers, you'll want to do two things: Find a reliable way to hire highly skilled freelancers even faster—and put a focus on your talent relationship management (TRM) efforts.

Freelance talent management: It's all about trust

When you work on building long-lasting relationships with top freelancers, you get to experience a new level of flexibility and agility. 

Rather than posting to multiple job boards, browsing LinkedIn, and finding a new freelancer each time you need help with a project, you can call upon a few select professionals who already know your brand inside and out.

By working with the same freelancers repeatedly, you establish a trusting relationship. This trust then enables you to take more off of your plate (and your mind). You can confidently hand off specific projects or tasks to a trusted freelancer and know that they'll complete the work on time in the way that you need. 

This frees you up to focus on other aspects of your work. Plus, you won't have to continually rebuild your talent pipeline.

To build up a roster of trusted freelancers, though, you need to have the right approach to talent relationship management.

Improve your approach to talent relationship management

Many freelancers are happy to establish long-term working relationships with clients. And sometimes, building a long-term relationship is as simple as a little outreach to see if a freelancer is open to ongoing or repeat contracts.

To boost the chances they'll say yes, though, you'll want to lay the groundwork for a good long-term relationship. This involves several of the same principles you already use when establishing relationships with other business partners or vendors.

Collaborate asynchronously

When you're working with multiple freelancers, keeping track of where everyone's files and messages are located can become tricky. Having one single point of asynchronous communication, such as Upwork Messages, makes working together easier for everyone.

"Upwork keeps a record of the client's previous projects and makes it available for me to see and understand my clients better," said Md Nayem, an AutoCAD professional and architectural designer who's logged more than 9,100 hours on client projects through Upwork. 

Features like Upwork's desktop time tracker and access to Uma™, Upwork's Mindful AI, make it easy for freelancers like Nayem to communicate with their clients, deliver work that aligns with client brands and guidelines, and keep long-term business objectives moving forward. 

‍

At the same time, clients like yourself can breathe easy knowing that you're always able to check in on project status, share files with your freelancer, and even bring internal team members into your contract workroom. 

Put a focus on clarity

Clarity, above all else, is key. When you're clear and detailed in your communication—especially the first time you hire a freelancer—you show them that you're easy to work with. Remember to:

• Be clear on what you need help with. Figure out what you want help with, what your budget is, and when you need deliverables before you search for freelancers on Upwork. This will help you find the right professionals to begin building a relationship with.
• Be ready to explain your project and company. If you have any brand guides or project briefs that the freelancer can review, including these in your initial messages can be very helpful.
• Be available. Freelancers will probably have questions as they begin to familiarize themselves with your company, project, and brand.

Remain flexible

You also need to be flexible when working with freelancers. The people you meet through Upwork are often self-employed—and may even be agency owners with team members.

This means that while you can certainly ask new hires to join you in your company's Slack workspace or project management tool (once your Upwork contract is active and you're done with onboarding, of course) they may have systems of their own that they use. You may even find that their processes are more efficient than your own!

Striking a good balance between how you both operate is helpful for building a lasting partnership. 

Show appreciation

If you're working with freelancers who are doing a great job, let them know! Showing appreciation to the pros you work with can go a long way toward increasing the likelihood they'll want to keep working with you on a long-term basis. 

I know that in my work as a freelancer, I love hearing how I've helped my clients—and I'm happy to keep supporting them in the same way. 

Remember that fair and competitive compensation is part of showing appreciation, too. It's normal for freelancers' rates to increase over time—and if they're doing a great job, agreeing to an increase may be well worth it in the long run.

Work toward mutual respect and trust

This may seem like it goes without saying, but mutual respect and trust are essential when you want to nurture relationships with freelancers.

Many of the freelancers in Upwork's talent community are highly skilled and have years of experience in their field. By approaching your work with them as a meeting of two professionals—versus a manager and subordinate mentality—you can begin to immediately convey respect for the freelancers you work with.

When you trust freelancers to bring your vision to life, and they trust that you respect them and their expertise, you can begin to form wonderful long-lasting partnerships that are fulfilling and valuable on both sides.

Common obstacles that hinder talent relationship building

Not all client and freelancer relationships are meant to last, and that's OK.

As a client, I've hired some wonderful freelancers on Upwork. Some of those initial contracts did turn into a longstanding relationship. Other times, though, I really just needed help with a short-term project and there wasn't any more work to be done.

Similarly, while working as a freelancer on Upwork I've had some great clients that I worked with once, and others that I continued to work with—on and off or steadily—for years. This is both natural and expected.

However, if you're finding it hard to build long-term relationships with freelancers you do want to work with on an ongoing basis, then you may be running into one of several common issues.

‍‍

Mismatched hiring

When your needs as a client aren't aligned with what freelancers can provide, you have what's known as a mismatched hire.

It doesn't matter how professional and skilled the freelancer you're working with is. If they can't provide the right services for your project, you might struggle to achieve the results you want. 

Finding the right freelancer typically starts with crafting a detailed and accurate job post. You don't have to know every specific detail about how a project will progress before you post your first job description—the freelancer you work with can often guide you through the project's execution based on their expertise. 

You should know the basics, though, such as whether you need a web designer or a web developer. If you're sourcing on Upwork, you can use our Job Post Generator powered by Uma to help you craft just the right post based on these basics. (The generator can really help to streamline your freelance talent acquisition workflow!) 

Once you've posted a job, remember to take your time reviewing proposals and portfolios—these are often more relevant to freelancing than a traditional resume. 

As tempting as it may be to reduce your time to hire as much as possible, you want to take a strategic approach to evaluating freelancers and finding the best option. If you need help with this, you can upgrade to a Business Plus plan and our Talent Specialists will create short lists of qualified freelancers upon request.

If you've already hired a freelancer and realize too late that you're mismatched, don't force it. Respectfully end your engagement with the freelancer following the terms of your agreement and look for someone else to work with.

Poor communication

Good communication isn't just about clarity—it's about communicating in the right way at the right time. This is especially important when hiring freelancers who work remotely.

When you meet with a freelancer for the first time, ask them about how they like to communicate…and when. Finding someone whose remote communication style meshes with yours can reduce friction in your working relationship.

This doesn't mean you have to be in the same time zone and regularly hop on real-time Zoom calls, though. Many Upwork clients have found success working asynchronously instead of synchronously. Some clients have even discovered that collaborating with freelancers around the world allows them to get more work done in a 24-hour period.

Scope creep

Scope creep is what happens when someone, typically the client, begins pushing a project outside of the original, agreed-upon parameters. This creep is often unintentional, but it can create strain on working relationships and leave freelancers feeling like their time isn't valued.

To avoid scope creep, start each project by defining a clear scope of work—and then be very intentional about sticking to it.

If you realize partway through a project that you need to make a change to the original scope or add on another deliverable, you can absolutely do this…after talking with the freelancer! Together, you may decide to:

• Extend a contract's end date
• Raise the weekly maximum hours on a contract
• Add another milestone
• Pay a bonus

Contractual friction

Other types of friction can emerge in a working relationship. Sometimes, the freelance hiring process itself can create stressors that result in a rocky start. These might include:

• Trying to communicate in real time when asynchronous communication would be better
• Trouble processing invoice payments
• Difficulty granting systems access for secure file sharing
• General disorganization around contract terms and start dates
• Concerns on both ends about losing money if a project doesn't go as planned

Using a human and AI-powered work marketplace like Upwork can help alleviate some of these friction points and create a smooth experience for everyone involved. This is true whether you're hiring for the first time or have been working with remote teams and freelancers for years.

Misclassification

Misclassification refers to a situation in which a worker is classified as an independent contractor, but they're really an employee. The same can happen in reverse.

While this can come with legal and tax implications for your business, it can also create friction between you and your favorite freelancers. Independent pros often choose to work on their own—and love doing so. Classifying them correctly is essential to making sure you can retain a working structure that all parties are interested in developing further.

Transactional mindsets

While it's important to classify your working relationship correctly, you also don't want to keep such a distance between yourself and freelancers that it feels cold and transactional.

Even though paying someone for their expertise is technically a transaction, you don't want to treat it as only that. If you go into your first freelance contract thinking of it in strictly transactional terms, you won't be in the right place to build a long-term professional relationship. Try to:

• Get to know the freelancers you work with. Talk with them as fellow professionals and learn about some of their likes, dislikes, hopes, and experiences.
• Act as a true collaborative partner. Ask for the freelancer's professional input, versus simply sending them a task list.
• Think of freelancers as new network connections. See if you can refer them to other people or ask if they can refer additional freelancers to you.
• Regularly revisit contracts. Reviewing your scope of work and rates can help to make sure your agreements are in line with the value a freelancer brings to your organization.

Use Upwork to find your favorite freelancers

Using Upwork is a great way to mitigate some of the common challenges that limit the development of long-term freelancer relationships.

"A lot of my Upwork project clients turn into long-term relationships," said Kate Harrison, a marketing strategist and writer. "The platform makes it all seamless." 

Consider doing the following to build your own long-lasting work relationships:

1. Take advantage of Upwork's communication tools. You can communicate via chat, Zoom, and phone all without leaving the Upwork platform. Sharing files is easy, too—and you always have a record of what was typed or shared in your workroom.
2. Rehire top freelancers. Your Upwork account contains a record of the freelance talent pool you've worked with in the past—along with metrics about your billing and usage history. In just a few clicks, you can review past projects, send any freelancer a message, or propose a new contract to begin working together again. 
3. Keep freelancers on retainer. If you find a freelancer you really like working with, consider creating a retainer. A retainer payment typically means that you can call upon freelancers if you need them. If you don't need their expertise in a given week, they still get the retainer payment—it's essentially compensation for their keeping time in their schedule to help you if needed. On Upwork, this is as simple as adding a "weekly payment" value to an hourly contract. 

‍

Start working with skilled freelancers this week

Begin building your pool of trusted freelancers today with an Upwork account. Whether you're comfortable finding freelancers in Talent Marketplace™ on your own, or you'd like help from our Talent Specialists, it's easy to find just the right pros for any project. New customers can sign up now for free.

Already an Upwork customer? Log into your account and take the Job Post Generator for a spin—or upgrade to Business Plus for added features, billing options, and on-demand support.

‍

This article is intended for educational purposes and should not be viewed as legal advice. Please consult a professional to find the solution that best fits your situation.

Upwork is not affiliated with and does not sponsor or endorse any of the tools or services discussed in this article. These tools and services are provided only as potential options, and each reader and company should take the time needed to adequately analyze and determine the tools or services that would best fit their specific needs and situation.