How to Work with Freelancers - 5 Steps to Success

Men freelancers working

Many people can start a business but successfully scaling one is a whole other story. Scaling is often a challenge because the business owner can’t afford to employ full-time staff or doesn’t know about outsourcing. 

It’s unfortunate because everything you need to grow your business is only a few clicks away. There’s a world full of highly skilled and self-motivated professionals waiting to help you grow your business.

This article aims to help you create a profitable and efficient collaboration between you and your freelance workforce. Doing so will enable you to scale your business and bring it to the next level. 

Why Work With Freelancers?

Working with freelancers is an excellent way to expand your team using professionals with diverse skill-sets.

Until recently, freelancers were mostly one gig operators, but more businesses now employ them as an ongoing integral part of their support team. 

Let’s find out how working with freelancers can bring value to your business. 


Flexibility is an essential element for dynamic business models as it enables you to react to market demands and implement strategies that take advantage of a situation as it’s happening.  

Freelancers bring flexibility to your business because of their geographical diversity and the ability to work while you sleep. For example, hiring a freelance social media manager based somewhere in Asia would enable your U.S. business to remain active 24/7 to engage a global community.  

Specialized skills 

Working with freelancers is like having a toolbox filled with the highest-quality equipment that’s at hand when you need them. 

The convenience is great, but it’s the quality of skill-sets, the ability of niche-specific hiring, and access to a diverse talent pool that makes working with freelancers so beneficial. 

Freelancers specialize in specific areas and have vast knowledge and experience working with clients with different expectations.  

Most businesses don’t need that level of expertise daily, but when you form a relationship with a skilled freelancer, they’ll be there when you need them. 

Budgetary constraints

Any outgoing, such as full-time employee costs, is an extra expense that most solo entrepreneurs and small business owners can’t afford. 

Working with freelancers enables you to employ skilled professionals without the ongoing costs of full-time employment. 

You can pay freelancers in one of 5 ways:

  1. By the hour
  2. By the day
  3. A retainer package
  4. By commission
  5. Project-based

Research shows you can save 20 to 30% per year by employing a freelancer compared with hiring an in-house employee. 

Time-sensitive projects

Finding and hiring people within your geographical location for a time-sensitive project means you’re dependent on a very shallow talent pool. 

Hiring permanent employees can take months while working with freelancers provides you with a global resource of eager professionals you can find and employ within a couple of days. 


A business with the right team flourishes, yet only 8% of today’s businesses scale successfully. 

One reason for this is an unproductive workforce as it reduces cash flow, limiting investment toward future growth.

Demand-driven and requirement-related hiring (i.e., working with freelancers) are how you get the highest value for your employment dollars. 

When you work with a freelancer, you can find the right people to suit your current requirements and bring in demand-driven professionals while evaluating which skills-sets you need next to scale your business.

Safe way to test ideas

Working with freelancers lets you test different business ideas for minimal costs because of reduced onboarding expenses and increased flexibility.

You can hire for single projects, test and evaluate the results, then choose to continue or change direction with no further outgoings as you’re not obligated to continue employment.  

Remote working 

Many freelancers work remotely, providing you with an endless source of employment opportunities and time-zone diversities. 

Working with freelancers provides you with a global business view; you can gain experience and insights from all 7 continents while saving on the outgoings of running a traditional office space. 

1. Sourcing Freelance Talent

Sourcing talent is when you research freelance candidates and then identify and convert a select few into potential job applicants.  

Sourcing enables you to connect with numerous candidates using popular freelance employment platforms.

And there are several to choose from:

Portfolio platforms

Portfolio platforms are where freelancers promote their work and advertise their skills to potential clients. Platforms like Dribble and Behance are where you’ll discover the world’s best freelance designers and creatives.   

Freelance marketplaces

Freelance marketplaces are where you’ll find and employ freelancers from every industry. These platforms enable freelancers to promote themselves and show previous examples of their work. 

And businesses like yours can advertise projects and allow freelancers to apply if their skills and experience match your requirements. 2 platforms most freelancers use are Fiverr and Upwork.

Upwork provides transparency about who you’re hiring and suits businesses that want to employ a freelancer repeatedly. 

Fiverr provides less transparency on who you’re hiring and is more suitable for one-off projects. 

Remote freelance job boards 

Job boards differ from freelance marketplace platforms as they’re where businesses advertise vacancies for job seekers. Dedicated remote freelance job boards enable global freelancers to find and apply for positions that would be impossible to find in their geographical location. 

Check out these 7 remote freelance websites:

Social networks

Social networks offer you a fantastic opportunity to find freelancers at the top of their game. 

Freelancers who use social media and microblogging sites like Twitter, Instagram, LinkedIn, Facebook, and Pinterest to promote themselves are often well experienced and leverage these platforms by promoting testimonials from past clients.  

You’ll find them by using search terms/keywords relevant to the role you need fulfilling.  

Referrals & offline networking 

Of course, recommendations from trusted associates are a great way to find reliable freelancers. Reach out to your network or go on LinkedIn and ask your connections for freelance referrals.

2. Hiring Freelancers

To find freelancers that fit your needs, write a detailed description outlining who and what you’re looking for, post it on a job board/platform, then interview applicants.

But before hiring, you need to know what questions to ask.

Questions you should ask

Asking the right questions separates unsuitable freelancers from those that could be a perfect fit. Consider asking these 10 questions before hiring your next freelancer.

  1. How do you charge?
  2. What are your rates? 
  3. How do you rate yourself?
  4. At what times are you available? 
  5. Can you work with deadlines? 
  6. Do you have a portfolio of past projects? 
  7. Can I contact past clients for references?
  8. How do you meet your clients’ needs? 
  9. Which communication channels do you prefer to use?
  10. Do you have any questions for me?

How does your budget impact your ability to hire?

Your budget plays a huge part in working with freelancers, especially when advertising on job boards and freelance platforms, since the best freelancers gravitate towards businesses offering the highest rates. 

Before advertising, begin by researching the average price for the service you need. If the going rate is $500 and your budget is $300, you might need to adjust to attract the best freelance talent. 

What is the screening process you should use to choose?

You can use a screening process to eliminate applicants who don’t meet your minimum requirements. A process saves you time and resources by not interviewing unsuitable candidates. 

Your screening process can include various elements, such as conducting video or phone interviews, reviewing past projects and resumes, or contacting previous freelancer clients. 

What should you be doing during onboarding?

Onboarding is the process of integrating freelancers into your business. 

The process can include an orientation process, so new hires understand your business’s culture, mission, vision, and values. 

When freelancers understand your company’s policies and culture, it removes any misunderstandings caused by remote working and communicating via email and text. 

A streamlined onboarding process would provide the following information:

How you should communicate with freelancers

When working with distant freelancers, you must account for any time zone and cultural differences concerning communications. 

For example, how often will you need to meet with them? Which platforms will you use? What are suitable times for live video calls? And do you have protocols for updates or additional requests? 

The clearer your communications are, the fewer problems you’ll have, and that’s better for everyone. 

Is a pilot project the more viable option?

Pilot projects are like test runs you use before committing to going all-in on developing a product, implementing a new business model, or working with a freelancer. 

With freelancers, a pilot project allows you to assess their skills and see if it’s a good working relationship while minimizing your investment and mitigating your risk.

3. Training Freelancers

When working with freelancers, it pays to form a strong relationship that benefits both parties.

A productive way to do this is by providing training initiatives that help your freelancer and increase the value they bring to your business. 

Let’s talk about tips for training freelancers:

How do you pass on your knowledge?

How you pass knowledge on to freelancers depends on the information they need and the tasks at hand. For remote access and immediate training, mobile on-demand/just-in-time learning is an excellent option. 

Mobile (or m-learning) is a modern way of providing cloud-based learning materials via mobile devices; it’s great for training staff that need instant learning modules. 

Mobile courses can be in-depth, but it also helps to use quick bites of information, known as microlearning. These bite-sized courses benefit workers needing just-in-time information that they can apply right away.

What kinds of resources and documents should you provide?

Your freelance workforce might need different resources to produce the best results.

It could be a software system, guidelines for completing or submitting work, access to internal documents, or regulations they must follow.

The more resources you provide freelancers, the better they’ll do their job. And freelancers love doing a great job, improving their skill-sets, and increasing their knowledge.  

How will you provide feedback?

To develop a long-lasting and productive working relationship with your team of freelancers, you must follow up and provide regular feedback. Remember, freelancers work alone and need to know if you’re happy or unhappy with their work so they can implement changes to meet your needs. 

Consider incentives

Incentives are rewards you offer freelancers for achieving specific goals or standards that benefit your business. A meaningful incentive could be to increase pay rates, specialized training, or a combination. Incentives suit businesses working with freelancers over long periods or projects. 

4. Managing Freelancers

Most freelancers are natural self-managers, require very little daily input from their employers, and appreciate the flexibility and space to get on with the job. 

However, you can bring value to your freelance workforce by providing project context, your end goals, and any recent changes that could affect their ability to complete tasks. 

Freelancers appreciate being updated and can often provide insightful insights and ideas when kept in the loop. 

Keep your freelancers motivated

Skilled freelancers with a strong work ethic are worth every cent they charge because they like a challenge, reaching targets, and surpassing goals.

To motivate those types of freelancers, you must:

Leveraging technology 

When you combine technology and freelancers, your business gets a superpower that could help you scale beyond expectations and evolve into a high-tech, modern-day, market-crushing machine. And you don’t have to be too tech-savvy to make it happen!

There are 3 such technology tools every business needs to succeed: Project management, time tracking, and chat tools.

Project management tools

Project management tools assist you and your team organize and manage projects and tasks of all sizes from any location. 5 cool project management tools to check out:

Time tracking tools

Time tracking tools allow you and your freelancers to record every hour spent while working. They’re a great way to track time spent on projects when paying freelancers an hourly rate.

Check out these time tracking software tools:

Chat tools

Chat tools enable you and your freelancers to chat in real-time and send text messages, videos, images, and hyperlinks. More advanced chat tools will allow you and your freelancers to share screens and take voice and video calls.

5 chat tools worth talking about:

Have a process to maintain quality control

Most freelancers work to a high standard; after all, their reputation is on the line.

However, when working with freelancers, you should implement a process that ensures everyone understands what’s expected and has access to your quality requirements.

Your quality control begins in the introductory stage and continues throughout every project until completion.

Provide freelancers with a list of rules and steps to follow so they can review when needed and provide you with high-quality results.

Set up your payment system and terms

Before working with freelancers, you must first figure out how you’ll pay them. As with most things, some options are better than others, and freelancers often have payment preferences.

Here are 5 ways to pay freelancers:

Avoid last-minute requests

Freelancers like a bit of notice for completing projects because it enables them to carry out adequate research and preparation. The best freelancers are rarely available at short notice, although some will take on rush jobs, but you should expect to pay more for the privilege.

Always think ahead and give yourself plenty of time when working with a freelancer so you’re not left waiting. 

5. Retaining Freelance Talents

Finding the best freelancers is one thing, keeping them is another. 

When you work with top-level freelancers, the last thing you want is to lose them. And for many businesses, retaining their freelance workforce is essential to their daily survival and future scaling aspirations. 

That’s why you must do everything you can to keep them; here’s how: 

Acknowledge good work

Yes, it’s simple but also effective. Freelancers work alone for long periods, and it’s often the clients who show their appreciation that gets their dedication. 

Make them feel part of the team

Ensure your freelancers feel part of your team by including them in meetings and introducing them to other team members. Encourage people to get to know one another and share their backgrounds, expertise, and achievements. It’s good for team morale and lets people know who to turn to with specific problems or questions.

Have feedback sessions

Feedback sessions are essential for retaining quality, consistency, and your freelancer’s loyalty. A little human contact goes a long way, and a feedback session ensures your team members interact and get to know one another. Organize regular feedback sessions with your freelancers and allow them to talk with managers, other team members, and yourself via online video calls. 

Always pay on time

Freelancers deserve to be paid on time and often choose reliable clients when deciding who to prioritize working with. 

Give raises when possible

Money plays a big part in retention and motivation, and often the more you pay a freelancer, the harder they’ll work. Go the extra mile, pay above average, and your freelance workforce will repay your commitment by supporting you and your business. Once that happens, the sky’s the limit.  


For modern businesses, the ability to work with freelancers is of paramount importance. It enables you to improvise, experiment, and work with a specialized talent pool that gives you a robust competitive edge in the dynamic market.

With a bit of care, foresight, and attention to detail, you should be able to build a lasting relationship with your freelancers. 

Now you know the essentials of working with freelancers. Let’s dig deeper and explore what to outsource and how to best approach it.  

This portion of our website is for informational purposes only. Tailor Brands is not a law firm, and none of the information on this website constitutes or is intended to convey legal advice. All statements, opinions, recommendations, and conclusions are solely the expression of the author and provided on an as-is basis. Accordingly, Tailor Brands is not responsible for the information and/or its accuracy or completeness.

Terry is a serial entrepreneur with over 25 years of experience building businesses across multiple industries – construction, real estate, e-commerce, hotelier, and now digital media. When not working, Terry likes to kick back and relax with family, explore Taoism’s mysteries, or savor the taste of fine Italian red wine.