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How To Hire an Independent Contractor

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How To Hire an Independent Contractor

How To Hire an Independent Contractor

Even if your business is fully staffed with excellent employees, there may come a time when you need some extra help. Independent contractors are a great solution for filling in skill set gaps, but they are not the same as part-time employees. 

Before you decide to hire an independent contractor, it is critical to understand what roles fall into that category in order to maintain legal compliance. 

What Is an Independent Contractor?

Hiring an independent contractor can benefit your business in many ways. By hiring an external professional to take care of an aspect of your business, you ensure high-quality work and free up your other employees to focus on their own responsibilities. 

For example, tax season may bring challenges best handled by a professional, but hiring someone full-time doesn’t seem like a good use of your budget. Instead, consider hiring an independent contractor. 

Independent contractors, also known as 1099 employees, are self-employed professionals who lend their services to corporations. Note that there is technically no such thing as a “1099 employee,” but the term is sometimes used because independent contractors are employees who fill out the 1099-NEC form. 

Independent contractors can be found in a range of industries, from creative work (including graphic design and copywriting) to financial advising and consulting. 

When an organization hires an independent contractor, they become the client rather than the employer. Therefore, organizations are not legally responsible for withholding taxes on behalf of independent contractors or providing any of the other conditions of employment extended to full or part-time employees. 

Unlike regular employees (or W2 employees), 1099 recipients are not part of the company’s payroll but instead submit invoices based on their completed work. 

Understanding Legal and Tax Implications

Individuals who receive Form 1099-NEC (Nonemployee Compensation) are not employees of your corporation and, therefore, are subject to different legal treatment. 

It’s important to stay current on federal and state employment laws to ensure legal compliance and maintain a positive relationship with your independent contractor. 

Legal Implications for Independent Contractors (1099 Recipients)

Independent Contractor Status

The line between a regular employee and an independent contractor can sometimes be blurred. Still, it is essential to properly classify your workers if you want to avoid legal issues and liabilities. 

Different jurisdictions have specific criteria to determine whether a worker is an employee or an independent contractor, so be sure to check your state’s employment laws regarding this matter. 


Trust is important for a successful working relationship between an independent contractor and an organization. However, a written contract is even more essential. 

The contract should outline the terms and conditions of the working relationship, including project scope, deliverables, payment terms, and other relevant details.

By creating stipulations for any foreseeable future scenarios, you take the guesswork out of the relationship and minimize the potential for conflict. 

Intellectual Property Rights

Imagine that you pay your independent contractor to create a unique advertising campaign for your organization. A few months later, you realize that one of your competitors is utilizing the same materials! 

Prevent this scenario by including stipulations for intellectual property rights in the contract. The contract should address who owns the intellectual property rights to the work created by the independent contractor during the engagement. 

The above situation can be prevented by clarifying to independent contractors that your organization will own all intellectual property they create on the job, ensuring they do not resell it to other clients. 

Non-Disclosure and Non-Compete Agreements

If sensitive information is involved in the assignment, including proprietary business information, consider including non-disclosure and non-compete clauses to protect your interests.

Employment Laws

Employment laws and regulations generally do not apply to independent contractors, but discrimination and harassment laws may still be relevant in some situations. 

Even if not legally required, best practices for maintaining a positive relationship with an independent contractor include protecting them from discrimination and harassment during their time with your organization. 


Independent contractors are not your employees, so your organization is not responsible for their insurance coverage. Independent contractors should have their own liability and professional insurance to protect themselves and their work.

Tax Implications for Independent Contractors (1099 Recipients)

Beyond unique legal requirements, independent contractors are also subject to different tax responsibilities than regular employees. 

Self-Employment Taxes

Independent contractors are considered self-employed and must pay both the employer and employee portions of Social Security and Medicare taxes. This is sometimes referred to as “self-employment tax.” 

Form 1099-NEC

If a business pays an independent contractor $600 or more in a tax year, they must issue a Form 1099-NEC to report the income to the IRS and the contractor. This can help ensure that the organization and the independent contractor report the same information to the IRS. 

Deductions and Expenses

Independent contractors can deduct business-related expenses from their income, which can help reduce their taxable income.

Estimated Tax Payments

Independent contractors are responsible for making quarterly estimated tax payments to cover their income and self-employment taxes.

No Withholding

Unlike employees, businesses do not withhold taxes from the payments made to independent contractors. Contractors are responsible for calculating and paying their taxes independently.

State and Local Taxes

Independent contractors are also subject to state and local tax requirements, which vary depending on their location.

It’s crucial to understand the legal and tax implications of hiring independent contractors to ensure compliance with applicable laws and regulations. If you have any doubts or specific questions about your situation, it’s best to consult with a qualified tax professional or legal advisor. 

Is an Independent Contractor Right for My Business? 

Now that you understand the difference between regular employees and independent contractors, how do you determine which is right for your business? 

When deciding whether to hire an employee or an independent contractor, you’ll need to consider several factors. 

Will this person be required to work set hours on company property, or will they have more flexibility? Will you work with them to establish a timeline for completing work, or will you set deadlines for when things need to be done? Will they be added to your company’s payroll or submit invoices? 

Though all of these questions are relevant, none of them can give the final word in determining how an employee should be classified. 

According to the IRS’s website, the most important question to ask is whether the employer (or client) can control only the result of the work — not what will be done or how it will be accomplished. In other words, only employers have the right to control the details of their employees’ work. 

If an organization is exerting more influence over an independent contractor’s work, they should most likely be reclassified as an employee. 

How To Hire an Independent Contractor

If you believe an independent contractor is right for your business, let’s dive into the details of the hiring process itself. 

1. Hiring Process Overview

When sourcing and selecting independent contractors, businesses should adopt a comprehensive approach to ensure they find the right candidates for their specific needs. 

Clearly define the roles and responsibilities for the position to write accurate job descriptions and identify the required skill sets.

Next, businesses should leverage various sourcing channels to attract a diverse pool of candidates. Online platforms like freelance marketplaces, industry-specific forums, and social media can be utilized to reach potential contractors with relevant expertise.

Once applications start coming in, a careful selection process is crucial. This can involve reviewing resumes, portfolios, or work samples to assess candidates’ qualifications and experience. 

Conducting interviews, either in person or through video calls, allows businesses to gauge the candidates’ communication skills and cultural fit.

Though the hiring process for independent contractors is similar to that for employees, it is extremely important to correctly classify the worker as a 1099 contractor, not an employee, as misclassification could lead to legal issues.

Furthermore, checking references and seeking feedback from previous clients or employers can provide valuable insights into a candidate’s work ethic and reliability. Businesses should also ensure that candidates possess the necessary tools, equipment, and workspace to effectively carry out their contractual duties.

Lastly, negotiating clear and comprehensive contracts is paramount to outlining the scope of work, payment terms, confidentiality agreements, and other pertinent terms and conditions. 

2. How To Write a Contract for an Independent Contractor

We’ve touched on the elements of establishing a contract, but it is very important to ensure that you include all potentially relevant information in this document. Strive to remove any potential for uncharted territory that could lead to a negative outcome. 

Introduction and Scope of Work

Begin the contract with an introduction that outlines the parties involved — the hiring party (the client or company) and the independent contractor. 

Clearly state the purpose of the contract, which is to define the scope of work and the services to be provided. Describe in detail the specific tasks and responsibilities the contractor will undertake. Include a concise description of the project’s objectives and deliverables. 

This section should also specify the project’s timeline, deadlines, and any important milestones. Providing a clear scope of work at the outset helps avoid misunderstandings and ensures both parties are on the same page.

Payment and Compensation

This paragraph details the payment terms and compensation structure for the independent contractor. Clearly state the agreed-upon rate or fees for the services provided, whether an hourly rate, fixed project fee, or other payment arrangement. 

Specify the method and frequency of payment (e.g., monthly, upon completion of milestones, or at the project’s conclusion). If there are any additional expenses or reimbursements the contractor is entitled to, such as travel or material costs, include them here. 

Be explicit about the invoicing process and the period within which the contractor should submit invoices. This section is crucial to ensure a smooth payment process and avoid any compensation disputes.

Confidentiality and Intellectual Property

Include a confidentiality clause in the contract to protect sensitive information and intellectual property. This paragraph should specify that the independent contractor agrees not to disclose any confidential or proprietary information obtained during the project.

Clearly define what constitutes confidential information and outline its protection and non-disclosure obligations. Additionally, address the issue of intellectual property rights. 

Clarify whether the contractor will retain ownership of any work they produce or if it will be considered “work for hire” and belong to the hiring party. Defining these rights upfront ensures a smooth handover of deliverables and avoids potential legal issues in the future.

3. Onboarding and Documentation

Beyond welcome information and the employment contract, there are a few additional documents you’ll need to provide while onboarding your independent contractor. 

Onboarding documentation for independent contractors typically covers compliance requirements, including tax forms and proof of eligibility to work. Contractors may also receive a comprehensive guide outlining safety protocols, workplace procedures, and emergency contact information to ensure a secure working environment.

To foster effective communication and collaboration, you may want to include contact details of key personnel and team members, enabling contractors to establish meaningful connections within the organization.

If necessary, this is also the time to provide any training the contractor can use to perform their job. This could encompass specific technical instructions, software tutorials, or project-specific guidelines to equip contractors with the necessary tools and knowledge to excel in their assignments.

4. Setting up Payment and Invoicing Systems

Setting up payment for independent contractors is a critical aspect of a smooth and transparent working relationship. A well-defined payment process must be established right from the onboarding stage to facilitate timely and accurate payments.

During the onboarding process, the contractor should provide the necessary financial information, such as bank account details, payment preferences, and any required tax documentation. This information allows the company’s finance department to set up the contractor in their payment system.

Once the contractor is onboarded, establish a clear payment schedule, specifying the frequency of payments (e.g., weekly, bi-weekly, or monthly) and the payment terms, including any applicable invoicing procedures. 

If the contractor is project-based, designate a milestone-based payment schedule in advance. Outlining this schedule in the contract will ensure everyone is on the same page while providing a structured approach to compensate for completed tasks or deliverables.

To ensure transparency and avoid payment disputes, the contract should explicitly state the agreed-upon payment rate, any additional expenses eligible for reimbursement, and the terms and conditions related to late or missed payments.

Regularly reviewing the payment process is crucial to address any issues that may arise promptly. Open communication channels with the finance team will enable contractors to seek clarification or resolve any payment-related concerns efficiently.

5. Managing the Working Relationship

Managing the working relationship with independent contractors is a delicate balance that requires effective communication, collaboration, and mutual respect. 

Clear expectations and goals should be established from the outset to ensure a successful partnership. Regular meetings or check-ins can be scheduled to discuss project progress, address any concerns, and share any changes in project scope, deadlines, or priorities. 

Regular constructive feedback can also help maintain performance standards and facilitate continuous improvement. Fight the tendency to focus only on negative feedback, as celebrating successes will boost morale and motivation.

Respecting the contractor’s autonomy and expertise is vital. Avoid micromanaging and allow them the freedom to execute their work in a manner they deem most effective while aligning with the project’s goals.

As with any working relationship, occasional challenges may arise. Addressing any conflicts or issues promptly and professionally can prevent them from escalating and maintain a positive working environment. 

Furthermore, understanding that independent contractors may have other clients and commitments can help accommodate their schedule and ensure a healthy work-life balance.

Overall, managing the working relationship with independent contractors requires clear communication, mutual trust, and a focus on shared goals. 

By nurturing a positive and supportive environment, the company can make the most of the contractor’s expertise, ensuring successful project outcomes and fruitful long-term collaboration.

6. Legal Best Practices

When hiring an independent contractor, it is crucial to abide by relevant laws and adhere to best practices to prevent potential legal issues. 

The first step is to ensure proper classification of the worker as an independent contractor, not an employee. Misclassifying employees as contractors can lead to significant legal liabilities, so understanding the IRS guidelines for determining worker classification is essential. 

Factors such as behavioral control, financial control, and the relationship between the parties should be considered when making this determination.

To establish a clear understanding of the engagement, create a written agreement outlining the terms of the contract. 

This agreement should include the scope of work, payment terms, project timeline, and any other relevant details. Emphasize in the contract that the worker is an independent contractor and not an employee.

7. Compliance with Labor and Employment Laws 

Though independent contractors don’t have the same rights and benefits as employees, there are still regulations that govern their treatment. 

Make sure you provide the contractor with a Form 1099-NEC at the end of the year if you paid them $600 or more for their services during the tax year.

Address insurance and liability matters by ensuring the contractor has adequate liability insurance and, if applicable, workers’ compensation coverage. Depending on the nature of their work, this coverage can protect both parties from potential risks.

Intellectual property ownership can be a sensitive issue, especially in creative projects. Include provisions in the contract that address the ownership of intellectual property created during the course of the engagement to avoid disputes down the line.

Consider having the contractor sign a Non-Disclosure Agreement (NDA) to protect confidential information. This agreement will help safeguard any sensitive data or trade secrets the contractor may encounter during the project.

Include a termination clause in the contract outlining the circumstances under which either party can end the engagement. This clause will provide clarity on the termination process and potential consequences.

It’s also essential to establish that the relationship between your business and the independent contractor is non-exclusive. This means the contractor is free to work for other clients during the engagement, emphasizing their independent status.

It can be highly beneficial to consult with an attorney or legal expert specializing in employment law or independent contractor arrangements to ensure full compliance with all applicable laws and regulations. 

By following these best practices, you can protect your business from legal challenges related to hiring independent contractors.

Evaluating Performance and Future Collaboration

Evaluating the performance of independent contractors is a critical aspect of successful project management and fostering productive collaborations. 

Set Clear Expectations

To begin, it is essential to set clear expectations and deliverables at the outset of the engagement. Defining the project’s objectives, timeline, and quality standards provides a solid foundation for assessing the contractor’s performance later on.

Throughout the project, regular monitoring of the contractor’s progress is necessary. This can be achieved through periodic check-ins, status updates, or milestone reviews. Maintaining open and constructive communication is equally important. 

Encouraging the contractor to share updates, ask questions, and seek clarification fosters a transparent working relationship. Likewise, providing feedback on their performance and acknowledging their successes shows appreciation for their efforts.

Evaluating Performance

When evaluating an independent contractor’s performance, several key aspects should be considered. First and foremost, assess the quality of their deliverables against the agreed-upon standards. 

The accuracy, completeness, and overall alignment with project objectives are crucial factors in gauging their work. Timeliness is also essential; a contractor’s ability to meet deadlines and complete tasks within the agreed-upon timeframe impacts project efficiency.

Professionalism and collaboration are other critical attributes to evaluate. Observing how well the contractor interacts with your team and handles communication with clients or other stakeholders gives insights into their ability to work well within the project environment. 

Additionally, assess their adaptability and problem-solving skills, as contractors who can navigate challenges and find creative solutions are valuable assets.

Gathering client feedback, especially if the contractor has worked directly with clients, provides an external perspective on their performance. This feedback can offer valuable insights and highlight areas for improvement. 

Make sure your observations are objective by utilizing measurable metrics. Key performance indicators (KPIs) such as project completion rate, error rate, or customer satisfaction scores can offer quantitative data to inform the evaluation process.

Assess Potential For Future Collaboration

Based on the evaluation, decisions about future collaborations with the independent contractor can be made. If their performance meets or exceeds expectations, continuing the collaboration on new projects can be a natural next step. 

In cases where improvements are needed, providing constructive feedback and discussing potential solutions can lead to positive changes. 

However, if the collaboration hasn’t been successful or isn’t aligned with future project requirements, it may be necessary to reassess the fit for future endeavors.


In conclusion, hiring an independent contractor can be a strategic and flexible solution for businesses seeking specialized expertise, cost-effective services, and increased operational efficiency. 

The benefits of engaging independent contractors extend beyond financial savings, as it allows companies to tap into a diverse pool of talents without the commitments associated with traditional employees. 

However, it is crucial to approach the hiring process with careful consideration, ensuring compliance with relevant laws and regulations and establishing clear contractual terms. 

By recognizing the unique advantages and potential challenges that come with engaging independent contractors, businesses can maximize their resources, foster innovation, and drive growth in an ever-evolving and competitive market landscape. 

Embracing this modern approach to workforce management can prove to be a valuable asset for businesses striving to remain agile and adaptive in the fast-paced world of today.


When should I hire an independent contractor?

Independent contractors are ideal for short-term projects, specialized tasks, or when you need expertise unavailable within your organization. They can be a cost-effective solution for businesses seeking specific skills without committing to long-term employment contracts.

How do I find independent contractors?

You can find independent contractors through various channels, such as online freelance marketplaces (e.g., Upwork, Freelancer), industry-specific job boards, networking events, or recommendations from colleagues.

Do I need to provide equipment or tools for the contractor?

Generally, independent contractors use their own tools and equipment to perform the services. However, in certain cases, you may agree to provide specific tools or resources necessary for the project.

How do I determine the contractor's fees?

The contractor’s fees can be negotiated based on the complexity of the project, the level of expertise required, the market rates for similar services, and the estimated time and effort involved.

Should I obtain insurance for the contractor's work?

While contractors are usually responsible for their insurance, it’s essential to clarify insurance requirements in the contract. Depending on the nature of the project, you might want to require the contractor to carry professional liability insurance.

How do I ensure the contractor's work quality?

Include performance metrics and milestones in the contract to measure the contractor’s progress and quality of work. Regular communication and progress updates can also help you stay informed about the project’s status.

Can I convert an independent contractor into an employee later?

Converting an independent contractor into an employee raises legal and tax considerations. Consult with a legal professional to ensure compliance with relevant labor laws and regulations in your jurisdiction.