10 Remote Hiring Best Practices and Tips 2023

Hiring independent talent provides so many benefits—ranging from reducing costs to increasing diversity and creativity—that businesses are adopting independent talent as a key part of their workforce strategy. In fact, nearly seven out of 10 hiring managers using freelancers plan to work with even more over the next two years.

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If you’re planning to work with more independent talent over the next few months, here are a few remote hiring best practices to consider. Implementing them may improve how smoothly your projects run and increase the quality of the work you receive.

1. Determine the work to be done by freelancers
2. Clarify the caliber of talent required
3. Write standout job descriptions
4. Hire for cultural add vs. cultural fit
5. Communicate regularly and extensively with your hiring partners
6. Establish a flawless interview process
7. Ask targeted interview questions
8. Establish a freelancer-specific onboarding process
9. Practice strong communication
10. Develop a strong culture

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1. Determine the work to be done by freelancers

With more work being done by freelancers, managers must be skilled at

• Breaking work or a large project down into chunks,
• Determining what skills are needed to complete them, and
• Deciding who the best person is to complete each parcel of work.

Sometimes, the decision is straightforward, such as when you need to quickly scale a team up and down or when you only need a certain skill for a project.

Other times, the decision may be more nuanced. Such as when you may be able to do the work in-house, but it may not be the best use of an employee’s time. For example, when the engineering team at PGA of America has a new idea, they contract independent developers to test proof of concept. Not only is it an efficient and cost-effective way to prove whether an idea is worth pursuing, but also full-time employees can remain focused on higher-value projects.

When you’re not crystal clear on whether a project should be done by employees or independent professionals, ask yourself these questions:

• Is the required skill available in-house?
• Is this work the best use of the employee’s time?
• What work will be sacrificed if the employee stops what they’re doing to handle the project?
• How will the additional project affect the employee’s workload balance?
• Can the employee execute the work at the quality required?

Related: 12 Reasons Why Companies Hire Freelancers

2. Clarify the caliber of talent required

In the past, many people thought of freelancers as people who did mainly entry-level administrative work. That’s just part of the talent available.

More than half (53%) of freelancers provide skilled services such as IT, computer programming, and data analytics. Most of them have postgraduate degrees and many are at the top of their field, with years of experience working for global enterprises. So, why are these in-demand professionals freelancing? Mainly so they can control their workdays and their careers.

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The point is, you can get a range of on-demand talent who match your project requirements. To determine who you need, many remote hiring best practices suggest you begin by listing the skills and tools they must know. Depending on where you search for talent, you may be able to find someone who checks off everything on your list.

For example, Upwork is the world’s largest work marketplace, offering more than 10,000 skills, with freelancers in more than 180 countries. That’s a huge pool of people. But don’t worry; Upwork’s advanced filters and search features make quick work of finding that golden unicorn with the exact mix of skills and experience on your wishlist.

One Upwork client needed help building a food data ontology, a model consisting of types, properties, and relationships. The ideal freelancer had to have a rare blend of knowing how to build ontologies, a detailed understanding of food, and an understanding of how to build software. The client found the exact person within two weeks on Upwork.

What many remote hiring best practices forget to mention is that in addition to hard skills, you should consider what soft skills (e.g., creativity, communication, problem-solving) the freelancer should possess too. Will they need to communicate with executives? Will they be explaining complex information to team members? Thinking through project scenarios can help you determine the soft skills required for them to deliver great work.

3. Write standout job descriptions

When hiring for any job, whether remote or in-person, you must convince someone to enter a relationship with you. So, just as much as talent must make efforts to convince companies to hire them, companies must convince talent to work with them. This courtship of sorts begins with your job post. Note that for project-based work, which is how most independent talent are engaged, you don’t need a full job description; those are only needed when you’re hiring employees.

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Example of a bad job post

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Example of a good job post

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Your project description doesn’t need to be long. The article How To Write a Job Description provides ideas on what to include. Here are the basics:

• Title: Make it detailed so that it grabs the attention of the ideal person you’d like to reach. For example, don’t say you’re looking for a writer, say you’re looking for a fashion blog writer to write five posts per month.

• Description of work you want performed: Include an overview of your project, its goals, deliverables, milestones, examples of related work to show the work quality expected, and any documents related to the project. The more clearly defined your description, the better the chances you’ll attract qualified people. And the more details talent have upfront, the more accurately they can provide cost and time estimates.

• Qualifications: List must-have hard and soft skills, experience, and knowledge. Don’t be shy about listing nice-to-haves as well. Just make sure to discern between the two lists so talent know if they qualify.

• Project specs: This may include project start and end dates, budget, and payment terms (fixed price or hourly).

4. Hire for cultural add vs. cultural fit

Numerous studies show the business case for building diverse teams, which makes sense, right? If you’re hiring people with the same background, mentality, gender, culture, and experience as you, you’re going to get the same thoughts, biases, and output.

An advantage of working with remote talent is that you can add diversity to your hiring best practices even when you have homogenous local talent pools. When you’re able to contract a freelancer who could be located in another state or country, you immediately have access to people with different mindsets, experiences, and backgrounds, all of which can greatly benefit your business performance.

Moadh Bukhash, Chief Marketing Officer at Emirates NBD, celebrates the diversity he gains by working with independent professionals through Upwork. In a Fortune article, he said that having the ability to access diverse talent increases his chances of success.

“Marketing is a game of diversity: The more diverse mentalities you have, the more ideas you’ll have, and the better stories you’ll tell. The better the stories, the greater the impact will be on your brand. When you have access to millions of talented freelancers and small agencies around the world, you’re increasing the probability that you’ll come up with something great, something unique, that will cut through the noise.”  
—Moadh Bukhash, CMO, Emirates NBD

5. Over-communicate with your hiring partners

Improve the quality of interviewees by working closely with your hiring partners to identify what a great fit looks like before they begin their search. For example, what you consider an intermediate-level 3D animator may look different to you than it does to a recruiter. And you may know some of the obstacles or challenging conditions the person will work under that a recruiter has no way of knowing.

When explaining to your hiring partners the work that the independent talent will do, for example, don’t just ask for a remote web developer. Let them know you need a web developer to create a custom plug-in for your WordPress site. Or that you need a web developer to redesign a Shopify site for higher customer conversions. The work they’ll do may impact where your partners look for talent and how they determine who qualifies for the work.

You may want to help your partners design the screening process for identifying and vetting qualified people. This may include designing assessments and suggesting interview questions.

If appropriate, let them know you’re open to considering people with different backgrounds than they may have delivered in the past. Your flexibility may widen your talent pool, which may enable them to find your ideal person sooner.

And give clear and timely feedback during every stage of the hiring process. The more you communicate, the better your outcomes will be.

6. Establish a flawless interview process for hiring remote freelance talent

One reason why more businesses are working with independent professionals is speed. According to Upwork clients, they fill job posts within three days on average. But having a shorter time to hire doesn’t mean you must short-change the interview process. In fact, having less time requires that you have a well-designed process so that you can determine the right fit faster.

How you design your interview process depends on your unique business needs. The marketing team at Singularity University uses Upwork regularly and designed a process that balances speed and stability at scale. For instance, team members are so accustomed to contracting talent that they can fill projects within 24 hours. However, they prefer that potential talent undergo two to three days of interviews to ensure they pick someone whom everyone approves.

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7. Ask targeted interview questions

You’re not going to learn much about the person’s qualifications by asking close-ended, yes/no questions like, “Do you like what you do?” and irrelevant questions like, “Where do you see yourself in five years?”

In the article on How To Conduct Remote Interviews, the author suggests asking a mix of questions to better assess the interviewee's competencies while keeping the conversation flowing naturally. Throughout an interview, you may want to ask a mix of:

• Technical questions to assess hard skills and overall knowledge
• Behavioral questions to assess soft skills
• Hypothetical questions to assess how they would react in a given situation

Interview questions should be designed to meet a project and business’s needs. You can review the 16 Best Interview Questions for Remote Workers for ideas. Consider asking questions that give insight to:

• Communication skills. Having someone who communicates clearly and respectfully, both asynchronously and synchronously, may help avoid miscommunication risk. Asynchronous communication happens over time, like email, and synchronous is immediate, like video meetings.
• Their enthusiasm for the opportunity. Do they seem genuinely interested in the project? If they’re lukewarm about the opportunity, it may reflect in their quality of work.‍
• Their technical aptitude. Do they seem comfortable with all the tools the project team regularly uses?

8. Establish a freelancer-specific onboarding process

Independent talent are accustomed to jumping into projects and getting started right away. But that doesn’t necessarily mean they want to work in a silo. As with any other worker, the more freelancers feel welcomed and valued for their contributions, the better their engagement and willingness to share new perspectives and ideas.

You can help them feel welcomed and get to work sooner by implementing a well-designed onboarding process. Here are a few tips from the article, How To Onboard Remote Workers:

• Complete paperwork. Have a way to securely complete and sign the required paperwork before they start work. If you contract talent through Upwork, a contract is automatically generated between the company and talent.
• Set up IT. To avoid project delays, ensure all systems permissions and security are set up before the person starts.
• Assign an onboarding buddy. If your project is longer term or complex, you may want to assign a buddy to the independent talent as a friendly point of contact to ask questions, help them settle in, and feel welcomed.
• Explain the company and business objectives. One Upwork client explains the company’s culture, mission, and values in a video. Videos offer a convenient and entertaining way for talent to understand the company and project purpose without having to read through pages of words.
• Provide insights into your brand voice. Understanding your brand voice isn’t only pertinent to independent marketing creatives and customer support agents; it can be helpful for anyone on any project. The better talent can speak the company’s language, the better they may communicate with team members.
• Set communication standards. Avoid misunderstandings from the start by clearly defining which communication tool to use for which situations. And share the speed of responses they can expect from you. Independent professionals may work with several clients at a time, so have them share what you can expect from them too.
• Meet the team. Not all projects require this, but if your project is longer term or complex, it may benefit everyone to gather online to kick off a project. This gives people a chance to get to know each other, which may improve communication and collaboration between team members.
• Distribute a list of contacts. Provide contact information of all the relevant people within your team, so they know who to contact when they need information or have an issue. Giving them the ability to solve issues on their own may reduce downtime, as the independent professional isn’t waiting for a single point of contact to get back to them.
• Have one-on-one check-ins. Throughout the project, check in one-on-one and at the team level, so the talent feels comfortable reaching out to other members when required.
• Set clear expectations. Before they dive into a project, review what’s expected of them. This may include defining what “good” work looks like, communication standards, milestones, deadlines, and deliverables.

9. Practice strong communication when hiring remote freelance talent

You can work with the same remote employees every day and still have occasional communication issues. Imagine what it’s like when you’re working with remote talent whom you’ve never met and will work with for only a short term. A lot can be misinterpreted. Someone may misread the tone of an email, think silence means they’re being ignored, or feel no one cares, so they don’t speak up when an issue arises.  

Miscommunication or a lack of communication can derail a project and potentially affect talent and employee morale in numerous ways. You can avoid such a fate by practicing strong communication with the talent and project team. Begin with the hiring process, continue throughout the project, and keep it up until the project is completed.

One of the most critical remote hiring best practices to remember is that you can’t over-communicate. These articles provide more ways to communicate effectively:

• How To Create a Project Management Communication Plan
• How To Improve Communication with Your Remote Team

10. Develop a strong culture for remote independent talent

Companies of all sizes, across most industries, are leveraging independent talent to keep business tracking towards growth.

In fact, two-thirds of Upwork’s roughly 2,500 team members are independent professionals, dedicated to the company’s mission and success.

“It’s easy to assume independent talent just get hired to complete a project and that they don’t have any vested interest in the company because they’re not an employee, but that’s not the case,” says Nathan Galteland, Director of Sales Operations at Upwork. “At times, they anticipate our needs and contribute more to the business than we ever expected.”

Galteland attributes their hybrid workforce success to personally vetting each person and Upwork’s culture of embracing independent talent. Many companies treat external professionals as second-class workers who come in for a one-off project, then leave. Instead, Upwork views them as remote specialists who are an important part of a team’s success.

Employees engage with independent professionals in various ways, such as by inviting them to attend virtual meetings and encouraging their input. “They feel part of our community and become just as bought into the success of our sales team and organization as our full-time people,” says Galteland. “To me, independent talent are as much a part of our team as employees.”

See how the engineering teams at Upwork use freelancers to scale.

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Find the ideal remote talent within 3 days

Many of the best practices in hiring remote talent follow eternal rules for successful relationships in any situation: Know what you want before reaching out, be respectful, be open to new ideas, and communicate. You can achieve this by shifting your hiring mindset and implementing a few processes to help you stay on track. Then the hardest part of hiring remote talent is finding them.

This is where Upwork can help. We intentionally designed our work marketplace to help connect the ideal talent with the ideal clients with greater ease and speed. It’s so easy to hire and work with independent professionals through Upwork that clients find their ideal people within three days on average. Or you can start a project the same day. If you’d rather not post a job and interview talent, browse Project Catalog™. There, you’ll find often-requested projects offered at set prices. Visit Upwork to get started.

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