How To Hire Contractors For Your Business Successfully

Master the art of hiring contractors with our expert tips and comprehensive guide.
Hire Contractors Successfully
Written by
Ontop Team

What is an Independent Contractor?

An independent contractor is a self-employed individual or business that provides services to another entity under the terms specified in a contract. Unlike employees, independent contractors operate independently, control their own working hours, and typically provide their own tools and equipment. They are not on the company’s payroll and are responsible for their own taxes.

8 Benefits To Hire an Independent Contractor?


Independent contractors provide a high level of flexibility, allowing businesses to hire them for specific projects or tasks. This is particularly beneficial for companies that experience seasonal fluctuations or have project-based work. By hiring contractors on an as-needed basis, businesses can adjust their workforce quickly in response to changing demands. This flexibility also allows companies to bring in additional expertise for short-term projects without the commitment of a permanent hire.


One of the most significant advantages of hiring independent contractors is cost savings. Contractors are not entitled to employee benefits such as health insurance, retirement plans, paid time off, or other perks typically provided to full-time employees. This reduction in benefits expenses can lead to substantial savings for the company. Additionally, businesses are not required to pay payroll taxes, unemployment insurance, or worker's compensation for contractors, further reducing overall costs. Companies also save on overhead expenses, as contractors usually work remotely and provide their own equipment and office space.


Independent contractors often bring a wealth of specialized skills and experience to a project. They typically have a deep understanding of their field and stay up-to-date with industry trends and best practices. This expertise can be invaluable, especially for tasks that require specialized knowledge or advanced technical skills. By hiring a contractor with specific expertise, businesses can ensure high-quality work and innovative solutions that might not be available in-house. This can be particularly advantageous for startups and small businesses that may not have the resources to hire full-time specialists.


The ability to scale operations up or down quickly is another major benefit of hiring independent contractors. Businesses can respond to market demands and growth opportunities without the long-term commitment of hiring full-time employees. This scalability is crucial for companies in dynamic industries where project needs can change rapidly. Contractors can be brought on board for the duration of a project and released once the project is completed, allowing businesses to manage their workforce efficiently and maintain agility in their operations. This approach also reduces the risks associated with overstaffing or understaffing.

Reduced Training Time

Independent contractors are typically hired for their expertise and experience, which means they require minimal training compared to new full-time employees. This reduces the time and resources spent on onboarding and training, allowing contractors to start contributing to projects almost immediately. Their prior experience and familiarity with industry standards enable them to integrate quickly and effectively into existing teams and workflows, accelerating project timelines and enhancing productivity.

Enhanced Focus on Core Business Functions

By outsourcing specific tasks or projects to independent contractors, businesses can free up their internal resources and focus on their core competencies. This allows full-time employees to concentrate on strategic initiatives and essential business functions, rather than being diverted by temporary or specialized tasks. Delegating work to contractors ensures that critical projects receive the attention they deserve while leveraging external expertise for ancillary tasks.

Access to a Global Talent Pool

The rise of remote work has made it easier than ever to hire independent contractors from around the world. This access to a global talent pool allows businesses to find the best candidates for their needs, regardless of geographic location. By tapping into international expertise, companies can benefit from diverse perspectives and innovative approaches to problem-solving. Additionally, hiring remote contractors can help businesses operate around the clock, with team members working in different time zones to accelerate project timelines and enhance overall productivity.

Risk Mitigation

Hiring independent contractors can also help mitigate certain risks associated with full-time employment. For instance, contractors are responsible for their own business expenses, liability insurance, and professional development. This reduces the financial and legal risks for the hiring company. Moreover, contractors often work under specific terms outlined in a contract, which can provide clarity and protection for both parties in case of disputes or project changes.

10 Key Aspect To Look for in an Independent Contractor

When hiring an independent contractor, consider the following factors to ensure you choose the right candidate for your project:

Relevant Experience

Experience is a critical factor in determining a contractor's ability to deliver quality work. Look for contractors who have a proven track record in the specific field relevant to your project. Experienced contractors are more likely to understand the nuances and complexities of the work, reducing the learning curve and increasing the likelihood of successful project completion. Review their portfolio, case studies, and previous projects to gauge their expertise and depth of experience.

References and Reviews

Checking references and online reviews can provide valuable insights into a contractor’s reliability, work ethic, and quality of work. Ask the contractor for references from previous clients or employers and follow up with these contacts to ask about their experiences. Look for patterns in the feedback you receive, such as consistent praise for meeting deadlines or frequent complaints about communication issues. Additionally, search for reviews on professional networks like LinkedIn or platforms where the contractor might be listed, such as Upwork or Freelancer.

Skill Set

Evaluate the contractor’s skill set to ensure it matches the specific requirements of your project. This includes both hard skills, such as technical abilities and industry knowledge, and soft skills, such as problem-solving and adaptability. Create a detailed job description outlining the essential skills and qualifications needed for the project, and assess candidates against this criteria. You might also consider giving them a small test project or task to verify their capabilities before committing to a larger engagement.


Confirm that the contractor’s availability aligns with your project timeline and deadlines. Discuss their current workload and ensure they can dedicate sufficient time and resources to your project. Misalignment in availability can lead to delays and unmet deadlines, so it’s crucial to establish clear expectations from the start. Ask about their typical response time for communications and their preferred working hours to ensure smooth collaboration throughout the project.

Communication Skills

Effective communication is vital for the success of any project, particularly when working with independent contractors who may not be physically present in your office. Assess the contractor’s communication skills during the initial interactions. Pay attention to their responsiveness, clarity in conveying ideas, and willingness to listen and understand your needs. Good communication helps prevent misunderstandings, keeps the project on track, and fosters a positive working relationship.

Professionalism and Reliability

Professionalism and reliability are key traits to look for in an independent contractor. Professional contractors are punctual, respectful, and deliver work as promised. They should have a strong work ethic, be self-motivated, and demonstrate a commitment to meeting project goals and deadlines. Look for indicators of professionalism in their initial interactions, such as timely responses to emails, a well-organized portfolio, and a clear understanding of your project requirements.

Flexibility and Adaptability

Projects often evolve, and having a contractor who is flexible and adaptable can be highly beneficial. Assess their ability to adjust to changing project needs and their willingness to go the extra mile to meet your requirements. Contractors who can think on their feet and adapt to new challenges will be more valuable in dynamic project environments.

Cultural Fit

While cultural fit is more commonly associated with hiring full-time employees, it can also be important when working with contractors, especially for long-term or collaborative projects. Consider whether the contractor’s values, work style, and personality align with your company’s culture. A good cultural fit can enhance teamwork, communication, and overall project harmony.

Legal and Financial Considerations

Ensure the contractor meets any legal and financial requirements necessary for the project. This includes having the appropriate licenses, insurance, and certifications. Verify their business registration and check for any legal issues or disputes that might affect their ability to complete the project. Additionally, discuss payment terms, invoicing procedures, and any other financial arrangements upfront to avoid misunderstandings later.

Technical Setup

For remote contractors, a reliable technical setup is essential. Ensure they have access to the necessary tools, software, and equipment required to complete the project. Discuss any specific technical requirements and confirm that they are well-equipped to handle them. A contractor with a strong technical setup will be more productive and less likely to encounter delays due to technical issues.

By carefully considering these factors, you can select an independent contractor who not only meets the technical requirements of your project but also fits well with your work environment and expectations. This thorough vetting process will help ensure a successful and productive collaboration.

How to Hire an Independent Contractor in 6 Steps

1. Find the Best Independent Contractor for You

Start by identifying potential contractors through various channels such as online platforms (Upwork, Freelancer), industry networks, and referrals. Evaluate their portfolios, experience, and client feedback to shortlist the best candidates.

2. Create an Independent Contractor Agreement

Draft a clear and comprehensive independent contractor agreement. This contract should outline the scope of work, deliverables, deadlines, payment terms, confidentiality clauses, and termination conditions. Ensure both parties understand and agree to the terms before starting the project.

3. Verify Compliance with Local Laws of the Contractor

Laws regarding independent contractors vary by location. Ensure compliance with local labor laws, tax regulations, and any industry-specific rules. This may include verifying the contractor’s business registration and ensuring they have the necessary licenses and insurance.

4. Organize the Appropriate Tax Information

As independent contractors are responsible for their own taxes, it’s crucial to gather the necessary tax information. In the U.S., this typically involves collecting a W-9 form from the contractor. For international contractors, you may need different forms or documentation.

5. Coordinate Work with the Independent Contractor

Effective communication and project management are key to a successful collaboration. Establish regular check-ins, use project management tools (such as Trello or Asana), and set clear expectations for deliverables and deadlines.

6. Pay the Independent Contractor

Agree on a payment schedule and method that suits both parties. Common payment methods include bank transfers, PayPal, and specialized platforms like Payoneer. Ensure timely and accurate payments to maintain a positive working relationship.

FAQs Independent Contractor for your business

When Should You Hire a Contractor?

Hiring a contractor is ideal in several scenarios:

  • Short-Term Projects: When you have a specific project with a defined timeline that requires specialized skills, hiring a contractor is a practical solution. This allows you to bring in expertise without a long-term commitment.
  • Specialized Skills: Contractors often possess unique or advanced skills that your current team may lack. Hiring a contractor can fill these gaps efficiently.
  • Seasonal Workload: If your business experiences seasonal fluctuations in workload, hiring contractors can help you manage busy periods without the need for permanent staff.
  • Cost Efficiency: When budget constraints are a concern, hiring contractors can be more cost-effective than full-time employees, as you avoid expenses related to benefits, training, and long-term salaries.

When Is It Best to Hire an Employee?

Hiring a full-time employee is advantageous in situations such as:

  • Ongoing Work: For tasks that require continuous attention and integration into the company’s core activities, a full-time employee is more suitable.
  • Company Culture: Employees are often more deeply integrated into the company's culture and long-term vision, contributing to a cohesive team environment.
  • Loyalty and Stability: Full-time employees may provide greater loyalty and stability, essential for roles that require a strong commitment and deep understanding of the business.
  • Complex Projects: Projects that involve extensive collaboration across departments and long-term planning are often better handled by full-time staff who are fully engaged in the company’s ecosystem.

How Do I Hire International Contractors and Stay Compliant?

Hiring international contractors requires careful attention to legal and regulatory compliance:

  • Understand Local Laws: Research the labor laws in the contractor’s country to ensure compliance with local regulations regarding independent contractors.
  • Contracts: Create a detailed contract that outlines the scope of work, payment terms, confidentiality, and other essential aspects. Make sure the contract adheres to the legal requirements of the contractor’s location.
  • Tax Compliance: Determine the tax implications for both your company and the contractor. You may need to withhold taxes or report payments to local tax authorities.
  • Payment Methods: Use reliable international payment platforms to ensure timely and secure payments. Platforms like PayPal, TransferWise (Wise), or Payoneer can help manage international transactions.
  • Consult Professionals: Engage with legal and tax professionals who specialize in international employment to navigate complex compliance issues.

Can I Hire International Contractors?

Yes, you can hire international contractors. Here’s how:

  • Platforms: Use freelance platforms like Upwork, Freelancer, or Toptal to find international contractors.
  • Networks: Leverage professional networks and referrals to identify skilled contractors globally.
  • Compliance: Ensure compliance with international laws and regulations, as mentioned earlier.
  • Communication: Establish clear communication channels and regular check-ins to manage projects effectively across time zones.

How to Create a Contract for an Independent Contractor

Creating a contract involves several key elements:

  • Scope of Work: Clearly define the tasks, deliverables, and deadlines expected from the contractor.
  • Payment Terms: Specify the payment amount, schedule, and method of payment. Include details on any expenses or additional costs.
  • Confidentiality: Include clauses to protect sensitive information and intellectual property.
  • Termination: Outline the conditions under which the contract can be terminated by either party.
  • Compliance: Ensure the contract complies with local laws and includes any necessary legal language specific to the contractor’s location.
  • Signatures: Ensure both parties sign the contract to formalize the agreement.

How Do I Manage Taxes for International Contractors?

Managing taxes for international contractors involves several steps:

  • Documentation: Collect necessary tax forms from contractors, such as W-8BEN for foreign individuals working with U.S. companies.
  • Withholding Taxes: Determine if you need to withhold taxes based on the contractor’s country and tax treaties.
  • Reporting: Report payments to the appropriate tax authorities as required by your country’s tax laws.
  • Professional Advice: Consult with tax professionals who specialize in international taxation to ensure compliance and optimize tax management.


Hiring independent contractors can be a game-changer for your business, offering flexibility, cost-effectiveness, and access to specialized expertise. However, managing the complexities of contracts, compliance, and payments can be daunting. With Ontop, you can handle everything from legal hiring and contract administration to compliance and international payroll - all in one place. Book a demo with us to see how we can help you scale your business.

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