How To Work With Freelancers in 8 Steps (Plus Pros and Cons)

Maybe you’re a “freelo” (freelancer) like me, who decided to be free and happy. Perhaps you have your own project and you want to work with freelancers. Maybe you’re building a serious and established team of remote workers and need to know how to make things work well with people who you don’t even know. Whatever the circumstance is, managing people and tasks isn’t easy. Even less if these people are creative, independent, dreamy, who don’t like fixed schedules, need to earn money, and defend their time, so they can have a life outside of work.

In order to do my job well, and not waste time or money, I did a lot of research to find out everything you need to know when it comes to working with people like me, or more complicated than me, and especially to not get any surprises down the road. In this post we’ll cover:

Here are seven tips for working with freelancers in your small business, for maximum success:
  1. Choose a Freelancer with the Right Skills. …
  2. Match Budget Expectations on Both Sides. …
  3. Make Sure Your Style Syncs Up. …
  4. Clearly Outline the Project. …
  5. Encourage Open Two-way Communication. …
  6. Start Small When Working with New Freelancers.

How To Make Money On Freelancer in 2022 (For Beginners)

Pros and cons of hiring freelancers

There can be both benefits and disadvantages to hiring freelancers at your company, including:


Here are the major advantages of incorporating freelancers into your staff:


Potential drawbacks to hiring freelancers include:

What is a freelance worker?

A freelance worker is a self-employed professional. Businesses hire freelancers to work for short or varying periods rather than as full-time employees. Also called independent contractors, freelancers typically work for multiple clients simultaneously.

Best practices for hiring freelancers to ensure quality work

Here are some best practices to follow during the hiring process for your freelancers:

Find high-quality freelancers

Search for great freelancers through methods such as:

Verify a freelancers credentials

During the hiring process, verify that your freelance candidates have the experiences and skills they claim they do. You can verify their credentials by asking them to provide references or researching their past work online. Depending on the type of freelance work youre looking for, you might also ask the freelancer to provide you with past samples of their work.

Evaluate the freelancers skills

Assess the freelancers abilities in relation to your business needs. Choose someone with the skill to achieve the goal of the freelance project. This includes ensuring that they can perform or complete the assignment with any style or techniques unique to your business.

Be patient during the search

It may take some time to find the right freelancer for the role and for your company. You might also need to hire a few before you find some that youd like to work with in the future. Be patient during the search and begin looking for your freelancer well in advance of when you need the task or assignment completed.

How to work with freelancers

Here is how to work with freelancers in eight steps:

1. Consider your businesss needs

Before beginning your search for freelancers, think about what your company needs from its freelance workforce. Take into consideration factors like:

2. Know the project requirements

Understand the projects scope, goals, style and schedule. Make sure that you and your freelancer can communicate clearly about these project specifications. Having established expectations for project goals and deadlines can help ensure that the eventual results meet your businesss needs.

3. Familiarize yourself with the laws

Learn both the local and national laws related to contractor employment. This can help ensure that both you and your freelancers produce quality work while adhering to these laws. Its also important to understand your businesss tax obligations in relation to contract work. For example, your payroll team should know that they dont need to withhold taxes from a freelancers wages.

4. Protect your company

Set up systems and legal documents to protect your companys assets. Make sure that your freelancer contracts specify that the work they complete belongs to your company. Its also a good idea to create data protection or cybersecurity systems that only give freelancers access to the company information they need to complete their specific assignments. This can help reduce the risk of a cyberattack on your businesss valuable data.

5. Make policies about contract work

Ask your HR department to design a set of policies regarding contract work. Details in the policy may include hiring standards, expectations for the contractors conduct and pay rates. Having clear HR policies that both you and your freelancers can review may help reduce miscommunications about the terms of their employment.

6. Begin with a small project

Give your new freelancer a minor project for their first assignment. Choosing a smaller assignment makes it easier for another employee to revise or redo the project as needed. It also gives them opportunities to ask questions about the assignment or your company while handling a manageable workload.

7. Design a transition plan

Create a transition plan that both you and your freelancers understand. The transition plan helps ensure your freelancers teach any work or knowledge necessary for other employees to know before their contract ends. For example, an IT freelancer may need to give another employee at your company a list of password or authentication systems they used to create cybersecurity infrastructure. Transition plans may involve the freelancer working closely with someone else from your company for a period or creating thorough documentation of their processes.

8. Monitor freelance assignments

Check in with your freelancers continuously. Periodically evaluating a freelancers ongoing work can help ensure that they ultimately provide satisfactory results or services. It also gives freelancers a chance to ask you questions or request company resources.

Soft skills to look for in freelancers

Some skills that you look for in your freelancers may depend on your businesss specific needs. However, regardless of the field, it can be valuable to look for those with certain soft skills, meaning personality traits or behaviors that affect their work performance. Soft skills to look for in your freelancers include:


Communication is one of the most important skills a freelancer can have. Since freelancers may work on different schedules or in a different location than the rest of your employees, its vital that they know how to communicate regularly and effectively. Search for a freelancer who can clearly and professionally convey their meaning through both written and verbal communication methods. They must also be able to actively listen to your companys needs, style and any other requirements or trends relevant to their project.


A freelancer should be able to adapt to changing situations or needs. If an unexpected issue arises during the project, they must know how to respond efficiently while staying calm. In addition, quality freelancers possess flexibility skills that help them balance multiple clients effectively and efficiently.


Freelancers typically work without direct supervision. This means that you need to hire those whom you trust to get their jobs done well and on time. Look for a professional with organization skills, time management abilities and self-motivation or self-direction.


Although freelancers often accomplish their work independently, they may also collaborate with other members of your company. They should know how to be an effective and positive member of a team. Teamwork skills to look for in freelancers include negotiation, cooperation and compromise.

Tips for maintaining relationships with freelancers

Here is some advice on how to maintain positive and professional relationships with your companys freelancers:

Communicate frequently

Encourage regular communication in both directions. A freelance employee should feel comfortable contacting you or asking questions as needed. Similarly, its okay for you to check in on your freelancer regularly to ask them how theyre doing, monitor their progress and provide any relevant updates on other project components.

Teach freelancers about your company culture

Teach freelancers about your company culture as part of their onboarding and training. Your company culture often influences the type or style of your services, products or processes. A freelancer may have an easier time completing their project in a way that aligns with your organizations aesthetic or approach if they understand your company culture. Teaching them about your company culture can also help facilitate or build stronger relationships between your freelancers and your regular employees.

Use communication tools

Use communication tools to remain in regular contact with your freelancers. These tools may include instant messaging systems, emails, phones, video conferencing programs or file-sharing software. Since most freelancers dont work on the same schedule or in the same premises as your regular employees, communication tools can help ensure that you communicate regularly about their ongoing projects.

Offer regular feedback on their work

Critique your freelancers work regularly. Tell them what you appreciate about their work and give constructive advice on what they might alter or improve. Offering consistent feedback can help ensure they only need to make small revisions rather than redoing an entire project from the beginning.


What to know when working with freelancers?

6 Things You Absolutely Must Know About Working with Freelancers
  • Vetting is Extremely Important.
  • You Need a Concrete Budget.
  • Managing Freelancers Isn’t Always Easy.
  • Set Ground Rules and Enforce Them.
  • Cheaper Isn’t Always Better.
  • Create Some Separation.
  • Know What You’re Signing Up For.

What skills do I need for freelancing?

Freelance skills
  • Communication. Communication skills help freelancers consult with clients on project requirements, like deadlines, materials and content. …
  • Negotiation. …
  • Industry knowledge. …
  • Marketing. …
  • Graphic design. …
  • Creativity. …
  • Project management. …
  • Empathy.

Can I do freelance work with no experience?

How to hire and manage freelancers: 12 tips
  1. Freelancers can benefit your company. …
  2. Freelancers are not full-time employees. …
  3. You need the proper infrastructure to support freelancers. …
  4. Define your need. …
  5. Craft a project description. …
  6. Share your freelance opportunity. …
  7. Screen potential freelancers. …
  8. Pay freelancers fairly.

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