Independent Contractor Paperwork: A Full Guide

If you are a business owner who hires independent contractors, you need to be aware of the paperwork involved in the process. Independent contractors are not employees, and they have different legal and tax obligations than regular workers. In this blog post, we will explain what independent contractors are, why you might want to hire them, and what documents you need to prepare and keep for them.

Understanding Independent Contractors

Freelancer doing work at her own pace

Independent contractors are self-employed individuals who provide goods or services to another entity under a specific contract or agreement. They are not subject to the same rules and regulations as employees, such as minimum wage, overtime pay, benefits, taxes, and workers' compensation. Instead, they are responsible for their own business expenses, taxes, insurance, and licenses.

Benefits of Hiring Independent Contractors

Hiring independent contractors can have many advantages for your business, such as:

  • Flexibility: You can hire independent contractors on a project-by-project basis, without committing to a long-term employment relationship. You can also adjust the scope and terms of the contract as needed, depending on your business needs and budget.
  • Cost-effectiveness: You can save money on payroll taxes, benefits, training, and overhead costs that you would otherwise incur with employees. You only pay for the work that is done, and you don't have to worry about paying for idle time or downtime.
  • Expertise: You can access specialized skills and knowledge that you may not have in-house, or that may be hard to find or retain in the labor market. You can also benefit from the experience and reputation of the independent contractor, who may have worked with other clients in your industry or niche.
  • Innovation: You can tap into the creativity and fresh perspective of the independent contractor, who may bring new ideas and solutions to your business challenges. You can also leverage their network and connections to expand your reach and exposure.

Key Documentation for Independent Contractors

Women reviewing the documents sent to her

When you hire an independent contractor, you need to make sure that you have the proper documentation in place to protect your interests and comply with the law. Here are some of the key documents that you should prepare and keep for each independent contractor:

Independent Contractor Agreement

An independent contractor agreement is a written contract that outlines the terms and conditions of the working relationship between you and the independent contractor. It is essential to have a written agreement to avoid any misunderstandings or disputes later on and to establish the status of the independent contractor as a non-employee.

Importance of a written agreement

A written agreement can help you:

  • Define the scope of work, deliverables, deadlines, payment terms, and other expectations for both parties.
  • Clarify the ownership and usage rights of any intellectual property or confidential information that is created or shared during the contract.
  • Specify how disputes will be resolved, such as through arbitration or mediation.
  • Reduce the risk of misclassification by the IRS or other authorities, which can result in penalties and liabilities for unpaid taxes, benefits, and wages.

Key components to include

  • The names and contact information of both parties.
  • A clear description of the services or products that the independent contractor will provide, and how they will be measured and evaluated.
  • The compensation amount and method, such as hourly rate, fixed fee, commission, or milestone payments.
  • The payment schedule and terms, such as invoicing frequency, due date, late fees, and expense reimbursement.
  • The duration of the contract and any renewal or termination clauses.
  • The ownership and licensing rights of any intellectual property or confidential information that is created or shared during the contract.
  • The confidentiality and non-disclosure obligations of both parties regarding any sensitive or proprietary information that is exchanged during the contract.
  • The indemnification and liability clauses that protect both parties from any damages or losses that may arise from the contract.
  • The dispute resolution process specifies how any conflicts or disagreements will be handled.
  • The signatures of both parties and the date of execution.

IRS Form W-9

IRS Form W-9 is a request for taxpayer identification number (TIN) and certification. It is used by businesses to collect information from their independent contractors for tax reporting purposes. As a business owner, you need to obtain a completed Form W-9 from each independent contractor before you pay them more than $600 in a calendar year. You also need to keep a copy of the Form W-9 for your records.

The Form W-9 includes:

  • The name and address of the independent contractor.
  • The TIN of the independent contractor, can be a social security number (SSN), an individual taxpayer identification number (ITIN), or an employer identification number (EIN).
  • - The certification that the TIN is correct and that the independent contractor is not subject to backup withholding or FATCA reporting.

You do not need to send Form W-9 to the IRS. However, you need to use it to prepare Form 1099-NEC, which is a report of nonemployee compensation that you pay to your independent contractors. You need to send Form 1099-NEC to the IRS and to the independent contractor by January 31 of the following year.

Proof of Insurance and Licenses

Depending on the type and nature of the work that the independent contractor performs, you may also need to obtain proof of insurance and licenses from them. 

This can help you avoid any liability or legal issues that may arise from the contract.

Some of the common types of insurance and licenses that independent contractors may need are:

  • General liability insurance: This covers any bodily injury or property damage that the independent contractor may cause to third parties while performing the contract.
  • Professional liability insurance: This covers any errors or omissions that the independent contractor may make while providing professional services, such as consulting, accounting, or legal advice.
  • Workers' compensation insurance: This covers any medical expenses or lost wages that the independent contractor may incur due to a work-related injury or illness. Some states require independent contractors to have workers' compensation insurance, even if they are not employees.
  • Business license: This is a permit that allows the independent contractor to operate their business in a certain jurisdiction. Some states and localities require independent contractors to have a business license, depending on the industry or activity they are involved in.
  • Occupational license: This is a credential that certifies the independent contractor's skills and qualifications in a specific profession or trade. Some occupations require independent contractors to have a license, such as doctors, lawyers, electricians, plumbers, etc.

As a business owner, you should request and verify the proof of insurance and licenses from your independent contractors before you hire them. You should also keep a copy of them for your records.

Understanding the IRS Guidelines

One of the most important aspects of hiring independent contractors is to understand how the IRS classifies them for tax purposes. The IRS uses three main criteria to determine whether a worker is an employee or an independent contractor:

  • Behavioural control: This refers to how much control you have over how the worker performs their work, such as when, where, and how they do it. If you have more control over these aspects, the worker is more likely to be an employee.
  • Financial control: This refers to how much control you have over the financial aspects of the working relationship, such as how you pay the worker, whether you reimburse their expenses, and whether you provide them with tools and equipment. If you have more control over these aspects, the worker is more likely to be an employee.
  • Relationship type: This refers to how you and the worker perceive your relationship, such as whether you have a written contract, whether you offer them benefits, and whether you expect the relationship to be ongoing or temporary. If you have a more formal and long-term relationship with the worker, they are more likely to be an employee.

The IRS does not have a clear-cut rule or formula for determining the worker's status. Instead, it looks at the totality of the circumstances and evaluates each case individually. Therefore, it is important to document and justify your classification decision based on these criteria.

If you misclassify an employee as an independent contractor, you may face serious consequences from the IRS, such as:

  • Back taxes: You may have to pay all the federal income tax and FICA tax (Social Security and Medicare) that you should have withheld from the employee's wages, plus interest and penalties.
  • Benefits: You may have to provide all the benefits that you should have offered to the employee, such as health insurance, retirement plan, paid leave, etc., plus interest and penalties.
  • Audits: You may trigger an audit from the IRS or other agencies, such as the Department of Labor or your state's labor department, which can result in further scrutiny and fines.

To avoid these risks, you should consult with a tax professional or an attorney before hiring an independent contractor. You should also review your existing contracts and relationships with your independent contractors regularly and make any necessary adjustments.

Compliance with Labor Laws


You will need to comply with other federal and state labour laws that apply to your business and industry. 

Some of these laws are:

Fair Labor Standards Act (FLSA)

The FLSA is a federal law that establishes minimum wage, overtime pay, recordkeeping, and child labor standards for employees. It does not apply to independent contractors. However, if you misclassify an employee as an independent contractor, you may violate the FLSA and face lawsuits and penalties.

State-Specific Labor Laws

Each state has its own labor laws that may differ from or supplement federal laws. Some of these laws cover topics such as minimum wage, overtime pay, sick leave, paid family leave, unemployment insurance, workers' compensation, anti-discrimination, anti-harassment, etc. You need to check with your state's labor department or consult with a lawyer to ensure that you comply with these laws.

Record-keeping and Document Retention

Storage and filing of documents

One of the most important aspects of working with independent contractors is keeping accurate and complete records of their work and payments. This is not only essential for tax purposes, but also for legal compliance and dispute resolution.

The IRS requires businesses to keep records of the following information for each independent contractor they hire:

  • Name, address, and taxpayer identification number (TIN)
  • The contract terms and scope of work
  • The amount and method of payment
  • The dates of payment
  • Any expenses reimbursed or deducted
  • Any forms or documents related to the contractor's tax status, such as Form W-9, Form 1099-NEC, or Form 1099-MISC

The IRS does not specify how long businesses should retain these records, but it is generally recommended to keep them for at least three years from the date of filing the relevant tax return. However, some states may have longer retention periods, so it is advisable to check with your state's tax authority or a qualified professional.

In addition to the IRS requirements, businesses should also keep records of any other documents that are relevant to the contractor's work, such as:

  • The independent contractor agreement and any amendments or modifications
  • Any invoices, receipts, or statements issued by the contractor
  • Any correspondence or communication with the contractor, such as emails, letters, or phone calls
  • Any performance reviews, feedback, or evaluations of the contractor's work
  • Any complaints, disputes, or legal actions involving the contractor

These records can help businesses protect themselves from potential lawsuits, audits, or investigations by proving the nature and terms of the contractor's work. They can also help businesses resolve any conflicts or issues that may arise with the contractor in a timely and professional manner.

Best Practices for Onboarding and Management

Hiring independent contractors can offer many benefits for businesses, such as flexibility, cost savings, and access to specialized skills. However, to ensure a successful and smooth collaboration, businesses should follow some best practices for onboarding and managing independent contractors.

Here are some tips to consider:

  • Provide a clear and detailed independent contractor agreement that outlines the expectations, deliverables, deadlines, payment terms, and other relevant clauses. Make sure both parties sign and date the agreement before starting the work.
  • Communicate regularly and effectively with the contractor throughout the project. Use the preferred method and frequency of communication agreed upon in the contract. Provide clear instructions, feedback, and support as needed.
  • Respect the contractor's autonomy and independence. Avoid micromanaging, controlling, or directing the contractor's work. Do not impose any rules or policies that are applicable to employees, such as working hours, dress code, or attendance. Do not provide any benefits or perks that are reserved for employees, such as health insurance, vacation time, or retirement plans.
  • Pay the contractor on time and in full according to the contract terms. Do not withhold any taxes or deductions from the contractor's payment. Issue a Form 1099-NEC or Form 1099-MISC to report the contractor's income to the IRS by January 31 of each year.
  • Review the contractor's work periodically and evaluate their performance. Provide constructive feedback and recognition for their achievements. Address any issues or problems promptly and professionally. If necessary, terminate the contract in accordance with the contract terms.


Independent contractors can be a valuable asset for businesses that need flexibility, efficiency, and expertise. However, working with independent contractors also comes with certain responsibilities and risks that businesses should be aware of and prepared for.

To ensure a successful and compliant relationship with independent contractors, businesses should follow these steps:

  • Understand what constitutes an independent contractor and how they differ from employees
  • Understand the benefits and drawbacks of hiring independent contractors
  • Prepare key documentation for independent contractors, such as independent contractor agreements, IRS Form W-9s, proof of insurance and licenses
  • Understand and follow the IRS guidelines for classifying and reporting independent contractors
  • Comply with federal and state labor laws that apply to independent contractors
  • Keep accurate and complete records of the contractor's work and payments
  • Follow best practices for onboarding and managing independent contractors

By following these steps, businesses can enjoy the advantages of working with independent contractors while minimizing the potential pitfalls.