How To Build Long-Term Relationships With Talent

If you’ve used Upwork before, then you’ve seen first hand how independent talent can help your business thrive. But you may have only scraped the surface of the true value this talent can bring to your organization.

To go one step further, you’ll want to begin building effective, long-term relationships with a core group of pros.

Why build strong working relationships with talent?

When you build long-lasting relationships with top independent talent on Upwork, you get to experience a new level of flexibility and agility.

Rather than finding new talent each time you need help with a project—and taking the time to brief them, check in, and review the work—you can call upon a few select individuals who already know your brand inside and out.

And because you’ve seen their work before, you know that you can trust them to deliver.

This trust then enables you to take more off of your plate, and your mind. You can confidently hand off specific projects or tasks, trusting that they’ll get done on time in the way that you need—freeing you up to focus on other aspects of your work.

How to build lasting relationships with top talent

Many independent professionals are happy to establish long-term working relationships with clients.

It’s easier, in many ways, for talent to work with repeat clients—they don’t need to spend extra time familiarizing themselves with a new industry and company each time they start a project. Instead, they’re able to dive in and put their skills to work right away.

“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, a junior architect and engineering draftsman who’s logged more than 8,500 hours on client projects through Upwork. These features allow Nayem—and other Upwork talent—to quickly learn, match, and use their clients’ desired tone and style to deliver high-quality work.

Sometimes, forming a long-term relationship with your favorite talent is as simple as asking if they’re open to ongoing or repeat contracts.

To boost the chances that 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.

Related: How To Hire Freelancers


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

  • Be clear on what you need help with before you begin searching for talent on Upwork. This will help you find the right talent to begin forming a relationship with.
  • Be ready to explain your project and your company. If you have any brand guides or project briefs that talent can review, including them in your messages can be very helpful.
  • Be available to answer talent questions as they familiarize themselves with your company, project, and brand.


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

This means that while you can certainly ask talent to join you in your company’s Slack workspace or project management tool—once your Upwork contract is active, of course—they may have systems of their own that they use. Striking a good balance between how you both operate is helpful for building a lasting partnership.


If you’re working with independent talent and think they’re 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 an independent professional, I love hearing how I’ve helped my clients—and I’m happy to keep supporting them in the same way.

Showing appreciation can be simple—you can:

  • Let talent know specifics about what you like in their work
  • Tell them how they’ve helped to make your life easier
  • Pass on positive feedback from others at your company
  • Share rave customer reviews or good campaign metrics
  • Offer to provide referrals and testimonials—including leaving feedback on Upwork profile pages

Mutual respect

This one may seem like it goes without saying, but mutual respect between clients and talent is essential for building a long-term relationship.

Many of the independent professionals on Upwork are highly skilled, with years of experience in their craft. By approaching your work with them as a meeting of two professionals—versus a manager and subordinate mentality—you can automatically begin to convey respect for the talent you’re working with.

Because Upwork gives you access to an entire world of talent, you might also work with people from different countries, cultures, and backgrounds. Being intentionally inclusive in your interactions can also help respect between all parties to flourish.


All of these elements, when combined, go a long way toward building trust between yourself and the independent talent you work with.

When you trust talent 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 to building relationships that last

Not all client and talent relationships are meant to last, and that’s okay.

As a client, I’ve hired some wonderful talent 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 talent 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 establish long-lasting relationships with talent that offer the kinds of services you do need on a regular basis, then you may be running into one of several common issues.

Mismatched hire

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

It doesn’t matter how professional and skilled the talent you’re working with is. If they can’t provide the right services for your project, things won’t get off the ground.

This is why clarity is so very, very important in establishing long-term relationships between client and talent.

You don’t have to know every specific detail about how a project will progress before you post your first job description. The independent professional you work with can often guide you through the process based on their expertise.

Do know, though, the basics—such as whether you need a web designer or a web developer.

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

Poor communication

Good communication isn’t just about clarity, either—it’s about communicating in the right way at the right time. This is especially important when hiring talent that’s working remotely.

When you meet with talent 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.

That 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 that working asynchronously when collaborating with global talent helps them get more work done in a 24-hour period—all by intentionally leveraging differences in time zones

If you aren’t used to remote work, don’t be afraid to tell your independent talent and ask them for advice. Whether they’ve been working remotely for years or for months, chances are they have some asynchronous work tips they can share.

Related: 14 Ways To Improve Remote Team Communication

Scope creep

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

Common examples of scope creep include:

  • Contracting talent to make Facebook and LinkedIn graphics, then requesting that they to do a set for another social media platform as well
  • Telling talent to write “just one more” marketing email when your agreement was for a fixed number of deliverables—that you’re happy with
  • Engaging talent to create a slide deck for your webinar series, and then asking them to create a blog to promote it
  • Hiring talent to develop an app for your startup, and then asking them to address bugs on your website at the same time

To avoid this, 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 to the talent about how best to handle it. This may look like:

  • Extending a contract’s end date
  • Raising the weekly maximum hours on a contract
  • Adding another milestone
  • Paying a bonus

Contractual friction

There are other types of friction that can emerge in a working relationship. Sometimes, the very process of hiring independent talent for the first time can create stressors that result in a rocky start. This 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 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 talent for the first time or have been working with remote teams and independent professionals for years.


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

If you send independent talent a computer to work on, require that they be in a specific work environment at set dates and times, or don’t have a contract in place, you could be inadvertently misclassifying them as an employee.

While this can come with legal and tax implications for your business, it can also create friction between you and talent. Independent professionals often choose to work on their own—and love doing so. Treating them as an employee, rather than a strategic partner, can create a relationship structure that they’re not interested in developing further.

Related: Safely Navigate The Future of Work

Transactional mindset

On the flip side, you don’t want to keep such a distance between yourself and the talent that your working relationship 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 engagement with talent thinking of it in transactional terms, you won’t be in the right mental space to begin cultivating a long-term professional relationship. Try to:

  • Get to know the talent you work with—talk to them as a person and get to know some of their likes, dislikes, hopes, and experiences
  • Act as a true collaborative partner and ask for their professional input, versus simply sending them a task list
  • Think of the talent you work with as new connections in your network, and see if you can refer them to other people or vice versa

You’ll want to build this kind of back-and-forth rapport on one-time projects, too. The person you hire for one quick project could wind up being someone you go back to in the future and form a long-term relationship with.

It’s also important to make sure that your contract rates are set in a way that reflects the value an independent professional brings to your organization.

Many independent professionals raise their rates at set intervals, such as annually. These rate increases can reflect their increasing expertise, familiarity with your brand, available service offerings, and normal cost of living fluctuations.

While talent will often let you know if their rates are increasing, it’s a good idea to regularly revisit your contracts and ensure you’re paying a competitive rate to your long-term collaborators.

How to use Upwork to find and retain top talent

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

Take advantage of Upwork’s communication tools

You can communicate via chat, video, phone call, and Loom videos all without leaving the Upwork platform. Sending files is easy too—and you always have a record of what was typed or shared in your Contract Workroom.

“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.”

Rehire top talent

Every Upwork client account includes a Virtual Talent Bench™ that makes it easy to see who you’ve hired in the past—and reach out to them again with another contract offer.

When I need to hire someone for a project, I always go back into my Virtual Talent Bench and message some professionals that I’ve worked with in the past. They aren’t always available, but if they are, I’m happy to hire them again.

Plus, doing so makes things easier on me. It’s a lot faster to simply send a few messages to folks I know and trust than it is to write a new job description, post it, review all of the proposals, and set up interviews.

Keep top talent on retainer

If you find talent who you really like working with, and want to ensure you can always tap into their expertise, consider creating a retainer.

On Upwork, this is as simple as adding a “weekly payment” value to an hourly contract. This is a fixed amount that’s paid to the talent you’re working with regardless of how many hours they logged for the week.

Typically, a retainer payment means that you can call upon talent if you need them. If you don’t need them in a given week, they still get the retainer payment—it’s essentially compensation for them keeping time in their schedule to help you if needed.

You and the talent will need to work out the terms of your retainer agreement, including its value and how much support or time they provide in return. It’s also smart to establish whether or not they’ll be able to bill additional hours on top of the retained time.

Source your own flexible, global talent pool

Start working smarter and more efficiently with your own global talent pool of pros with the specific skill sets you need. It all starts here, on the world’s work marketplace, where independent talent acquisition is easy.

Browse Project Catalog™ to view available services, post a job in Talent Marketplace™ to find talent with specific competencies, or get help from skilled staffing specialists who work with our Upwork Enterprise clients. All it takes is an Upwork account—sign up or log in now to get started.

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.

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Author Spotlight

How To Build Long-Term Relationships With Talent
Emily Gertenbach
B2B SEO Content Writer & Consultant

Emily Gertenbach is a B2B writer who creates SEO content for humans, not just algorithms. As a former news correspondent, she loves digging into research and breaking down technical topics. She specializes in helping independent marketing professionals and martech SaaS companies connect with their ideal business clients through organic search.

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