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Utilizing Contractors for Your Business: Effective Strategies for Working with Freelancers


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When you’re running a business, sometimes you need a little extra help. This is where contractors, or freelancers, come into play. These people aren’t part of your regular staff but are hired to do specific jobs on a project-by-project basis. Contractors are especially useful for jobs that require special skills that your current team might not have. In this blog, we’ll break down how to find and work with contractors effectively and how to handle the money side of things.

What Are Contractors?

Contractors work independently, not as full-time employees of a company. They often specialize in particular areas, such as writing, graphic design, or tech services. Since they aren’t on the company payroll like regular employees, they handle their taxes and usually work remotely or on their schedule. Businesses use contractors because they can hire them only when needed and for specific tasks, which can save money.

Types of Contractors

Here’s a quick look at some common types of contractors you might need:

  • Creative Contractors include graphic designers, writers, and video creators who can help with anything from designing a logo to writing blog posts.
  • Tech Contractors are software or IT support experts who can help set up systems or create websites.
  • Administrative Contractors: These could be virtual assistants who help manage emails, schedule appointments, or handle data entry.
  • Professional Consultants: This group includes specialists like marketing strategists or financial advisors who provide expert advice.
  • Manual Labor Contractors are skilled individuals like carpenters or electricians who perform physical work that requires specific skills.

Independent Contractor vs. Freelancer: Understanding the Differences

“independent contractor” and “freelancer” are often used interchangeably, but they can mean slightly different things depending on the context. Generally, both are self-employed individuals who provide services to different businesses. The key similarity is that neither is considered an employee of their companies, so they handle their taxes and benefits.

  • Independent Contractor: This term is commonly used in a legal and formal context. It often refers to someone who works with one or more companies on a contract basis. They might provide specialized services like plumbing, consulting, or construction.
  • Freelancer: This term is usually less formal and often associated with creative or tech fields, such as writing, graphic design, software development, or photography. Freelancers might juggle multiple small projects or clients at once and often find work through online platforms.

How to Manage Your Team of Contractors or Freelancers

Managing a team of freelancers or contractors involves clear communication and organization. Here’s how you can effectively manage them:

  1. Set Clear Expectations: From the start, be clear about what tasks need to be done, when they are due, and how much you will pay. Clear instructions can prevent confusion and ensure that work is completed to your satisfaction.
  2. Use Project Management Tools: Tools like Clickup,, Notion, or Slack can help keep everyone on track. These tools allow you to assign tasks, track progress, and communicate in one place.
  3. Schedule Regular Check-Ins: Regular meetings (either video calls or chats) can help address any questions and update you on progress. This helps everyone stay aligned and can build a stronger working relationship.
  4. Provide Feedback: Offering constructive feedback helps improve the quality of work and makes your contractors feel valued and understood, which can encourage better work in the future.

Finding Freelancers or Independent Contractors

Finding the right person for the job is easier than ever thanks to several online platforms:

  • Fiverr: This is a great place to find freelancers who offer various services starting at just $5. It’s perfect for when you need a small job done quickly.

Get Started with Fiverr Now 

  • Upwork: Here, you can post a job description and get bids from freelancers worldwide. It’s good for both short and long-term projects.

Get Started with Upwork Now 

  • Paired: If you’re looking to save money by hiring from overseas, Paired can connect you with talented people from different countries. This is especially helpful if you want to build a team to handle tasks like managing a YouTube channel or other ongoing work.

Using Paired to Grow Your Business

Paired is a helpful tool to expand your business without spending much money. Here’s why you might consider using Paired:

  • Save Money: Hiring freelancers from countries with lower living costs can save you up to 80%-90% of what you usually pay.
  • Find Quality Help: Paired looks for people who are skilled,nicating, and committed to their work.
  • Flexible Hiring: Whether you need someone for a one-time project or something more permanent, Paired offers flexibility.

How Much Does Paired Cost?

With Paired, the cost will depend on the project details and the freelancers’ rates. Since you discuss and agree on fees directly, you can often find services that fit your budget.

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How to Pay Independent Contractors or Freelancers

Paying freelancers or contractors is straightforward, but you need to keep some things in mind:

  • Agree on Payment Terms Early: Before starting work, discuss and agree on the rate (hourly, per project, etc.), payment schedule, and methods. Popular payment methods include PayPal, bank transfers, and services like Deel.

    You can watch our channel on ‘How to Pay Contractors Internationally with Deel’ 

  • Send Invoices:  Ask your freelancers to send invoices for their work for record-keeping and tax purposes. Invoices should detail the services provided, the amount due, and the date.
  • Timely Payments: Pay your freelancers on time according to the agreed schedule. This builds trust and ensures a good relationship.

Tips on Hiring the Best Contractors or Freelancers

Finding the right people can make a big difference. Here are some tips for hiring the best:

  1. Look at Portfolios and Reviews: For creative or technical services, review the freelancer’s previous work and read client reviews. This can give you a good sense of their quality and reliability.
  2. Start with a Small Test Project: Start with a small project to see how well the freelancer meets your needs. This can help you assess their skills and work ethic before committing to a larger project.
  3. Ask for Recommendations: Sometimes, the best way to find trusted freelancers is to ask other business owners or colleagues for recommendations.
  4. Communicate Clearly: When discussing a potential project, be clear about your needs and expectations. Good communication can help you gauge how well the freelancer understands your project.

Managing Taxes for Contractors

Handling taxes for contractors is different from dealing with regular employees. Here are a few tips:

  • Use Form 1099: In the U.S., if you pay a contractor more than $600 in a year, you need to fill out a Form 1099-NEC. This form reports to the IRS how much you paid the contractor.
  • Tax Deductions: The money you pay contractors can usually be deducted from your business’s income on your tax returns, saving you money.
  • Contractor’s Tax Responsibility: It’s important to remember that contractors handle their taxes. You don’t need to withhold taxes from their pay like you would for an employee.


Working with contractors can be a smart move for your business. It allows you to get specialized help only when needed, without the cost of hiring full-time staff. Online platforms like Fiverr, Upwork, and Paired make finding the right people for the job easy. Just ensure you understand how to manage payments and taxes properly to keep everything running smoothly. Whether you’re just starting or looking to expand, bringing in the right contractors at the right time can help your business grow and succeed.

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