Tag: misclassification

New York Independent Contractor Audit

Conducting a New York Independent Contractor Audit

If your business relies on independent contractors—whether in New York or elsewhere—you’ve likely heard that misclassification can lead to serious legal trouble. But for companies with individuals physically performing services in New York, the risks have only intensified in recent years. That’s why now is the time to perform a New York independent contractor audit of your existing relationships.

Why This Matters Now

New York State has significantly expanded protections for freelancers and increased its scrutiny of worker classification. With the 2024 enactment of the Freelance Isn’t Free Act and ongoing state and federal enforcement actions, it’s more important than ever to evaluate whether your independent contractor arrangements truly comply with the law.

Misclassifying an employee as an independent contractor can lead to liability for:

  • Unpaid minimum wage and overtime

  • Unpaid unemployment insurance and workers’ compensation contributions

  • Interest and penalties from tax authorities

  • Legal fees and liquidated damages in private lawsuits

  • Liability under New York’s Freelance Isn’t Free Act

In addition, enforcement efforts are increasing:

  • The New York State Department of Labor (NYSDOL) continues to aggressively investigate misclassification claims.

  • The IRS and state/local tax authorities remain interested in employer tax compliance.

  • Private litigation and class actions are becoming more common, particularly where workers are denied benefits or final payment.

Bottom line: if someone is working in New York—physically, even remotely—your business may be subject to New York’s worker classification rules, regardless of where your headquarters or other business locations are located.

Step 1: Know the Legal Standard (It’s Not the Same Everywhere)

In New York, the legal tests for employee vs. contractor status vary depending on the law at issue. That complexity is a common pitfall for employers.

For Wage and Hour Purposes:

New York follows a multi-factor “economic realities” test, similar to the federal DOL standard. The core question: Is the worker economically dependent on the business or truly in business for themselves?

Relevant factors include:

  • The degree of control the business exercises over the work

  • The worker’s opportunity for profit or loss

  • The permanency of the relationship

  • The extent to which the work is integral to the business

  • The skill and initiative required

  • The extent of the worker’s investment in tools or equipment

No one factor is determinative. Control is important, but courts and agencies look at the totality of the relationship.

For Unemployment Insurance:

New York applies a worker-friendly test, meaning it is easier for a worker to be deemed an employee eligible for unemployment insurance. The NYSDOL looks primarily at whether the employer exercises any degree of supervision, direction, or control over the worker’s services. This includes not just direct oversight, but also indirect control, such as setting hours, assigning work, or requiring status reports.

As a result, a worker may be classified as an independent contractor for federal tax purposes under IRS standards, yet still be considered an employee for New York unemployment insurance eligibility.

For Freelance Isn’t Free Act Compliance:

Even if the contractor is properly classified, businesses must comply with New York’s new requirements for freelance contracts. For independent contractors in New York earning $800 or more, a written contract must exist, identifying payment timelines and retaliation protections.

Click here for more on New York’s Freelance Isn’t Free Act.

Step 2: Conduct an Internal Audit

An internal audit is your best defense against future liability. Start by identifying anyone providing services to your business who is not on payroll. Then, for each worker:

Conduct an Audit

1. Document the Relationship

  • Do you have a signed contract?

  • Does the contract describe an independent business relationship, with clear project-based deliverables and no guarantee of ongoing work?

  • Is the contract consistent with how the relationship works in practice?

2. Evaluate Control

  • Who sets the worker’s hours?

  • Where is the work performed?

  • Who provides tools, equipment, and software?

  • Do you require regular check-ins or approval for routine tasks?

3. Assess Economic Independence

  • Does the worker have other clients?

  • Do they advertise their services publicly?

  • Can they subcontract the work or delegate it?

4. Examine Duration and Integration

  • Has this person worked with you for years on repeat assignments?

  • Is their work central to your business function?

Red flags may include:

  • Contractors working set hours or reporting to a manager

  • Use of internal email addresses or being listed on the company website

  • Reimbursement of expenses that should be borne by the contractor

  • Prohibitions on working for other clients

In most cases, there are no single factors that are entirely determinative of the proper classification. Multiple criteria must be considered. But the presence of any of the above red flags should generally trigger further analysis.

Step 3: Address the Risks

After identifying questionable arrangements, you have a few options:

Option 1: Reclassify as an Employee

  • This may be the safest course, especially if the worker is full-time, works under close supervision, or performs a core function of your business.

  • It may also open access to benefits, improve morale, and reduce turnover.

Option 2: Restructure the Relationship

  • Limit control and supervision.

  • Update the contract to emphasize the contractor’s independence.

  • Avoid integrating the worker into your business structure (e.g., no internal email, no title).

Option 3: Continue the Relationship with Mitigation Measures

  • Require evidence of the contractor’s separate business (e.g., EIN, business insurance, W-9).

  • Educate your managers on boundaries to maintain independence.

  • Set project-based deliverables with defined scopes and deadlines.

Step 4: Consider the Impact of Remote Work

New York Remote Worker

Employers sometimes overlook that remote workers still “perform services” in a physical location—namely, wherever they are sitting with their laptop. If that’s New York, your business may need to:

  • Register for a New York employer ID

  • Comply with NY wage and hour laws

  • Withhold and remit NY state taxes and unemployment contributions

  • Follow the Freelance Isn’t Free Act if you engage independent contractors based in New York

Step 5: Train and Monitor

The law is clear: labels don’t matter—substance does.

Train your managers and HR personnel not to treat contractors like employees. Common mistakes include:

  • Directing day-to-day work

  • Including contractors in internal Slack or Teams channels unrelated to their assignment

  • Having contractors attend staff meetings or performance reviews

Monitor the relationships over time. What starts as a one-off project can evolve into an employment relationship if not carefully maintained.

Don’t Ignore This Potential Source of Serious Liability

The financial implications of improper classification depend on how many people are involved, the volume of their work, and other considerations. But it can result in fines, penalties, backpay, liquidated damages, and more. All of that adds up quickly and, in some cases, the liability can accrue to individuals, such as business owners, who may not be able to easily escape it even through bankruptcy or other business dissolution.

If you’re unsure whether your contractor relationships would withstand scrutiny from the NYSDOL, the IRS, or a plaintiff’s attorney, now is the time to act. And if you engage any freelancers in New York—whether directly or through third parties—you’ll want to ensure that your contracts and processes are updated to comply with both classification standards and the Freelance Isn’t Free Act.

Given the complexity of the applicable classification standards, consulting with an experienced employment attorney is recommended if there is any uncertainty whether someone is properly treated as an independent contractor.

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Model Freelancer Contract

NYS Model Freelancer Contract

New York State’s Freelance Isn’t Free Act took (FIFA) effect on August 28, 2024. As required by the Act, the New York State Department of Labor has developed a model freelancer contract. Although the model agreement meets the legal requirements, it has serious limitations. Accordingly, most hiring parties should consider modifying the model contract or drafting their own FIFA-compliant agreement.

Freelance Isn’t Free Act Overview

New York’s FIFA addresses non-employment relationships between a “hiring party” and a “freelance worker.” Under this law, only individuals and single-person organizations can qualify as a “freelance worker.”

When a hiring party engages a freelance worker, there must be a written contract between them.

By law, the contract must contain the following information:

  • Name and mailing address of both the hiring party and the freelance worker
  • Itemization of all services to be provided by the freelance worker
  • Value of the services to be provided
  • Rate and method of compensation
  • Date or mechanism of determining when payment will be made
  • Date by which a freelance worker must submit a list of services rendered to allow the hiring party to process timely payment

Hiring parties that don’t ensure there is a compliant contract in place risk various penalties. But the biggest risks aren’t just not having a written contract.

Purpose of the Freelance Isn’t Free Act

More than insisting on a written contract, FIFA is designed to give non-employees compensation protections similar to those of employees. Instead of typical breach of contract damages, FIFA allows freelancers to recover enhanced penalties as are available for unpaid wage claims. Consequently, hiring parties face significant liability risk when they don’t pay a freelancer in full and on time.

Click here for more on the FIFA requirements.

Components of the Model Freelancer Contract

The DOL’s model freelancer contract contains 25 numbered sections. These include identification of the parties, compensation terms, and various provisions referring to the freelance worker’s rights under FIFA. It appears the latter content goes beyond what the law actually requires.

Such additional provisions include those with the following headers:

  • Prohibition Against Waiver
  • Prohibition Against Retaliation and Discrimination
  • Violations

The template also includes the following provisions that may not be desirable (at least as written) in all contexts:

  • Intellectual Property Rights
  • Revisions
  • Termination
  • Indemnification
  • Insurance Required
  • Other Business Activity
  • Late Payment
  • Limitations on Liability
  • Confidential Information

The NYS DOL template “Freelance Worker Agreement” is available here.

Model Freelancer Contract Doesn’t Avoid Employment Relationship

By using the model freelancer contract as written, hiring parties would not only be telling freelancers how to pursue claims against them, but may also unwittingly jeopardize the independent contractor nature of the relationship.

The model contract states that “Nothing in this Agreement shall indicate the Freelance Worker is a partner, agent, or employee of the Hiring Party.” But it doesn’t specifically acknowledge that the freelancer is not an employee! Plus, the check-box, fill-in-the-blank format of other sections could result in terms that may support an employment classification.

Remember, a hiring party and worker can’t simply decide whether they have an employment relationship or not. That is always a question that could be determined by a court or government agency for various purposes after the fact. And the laws often operate on the assumption of an employment relationship (with the attendant legal consequences). Typically, the burden is on the hiring party to demonstrate that no employment exists, regardless of what the worker intended when entering into the arrangement.

Other aspects of the template agreement could also unwittingly support an employment arrangement. For example, providing an hourly pay rate and certain insurance coverages may be more typical for employees.

Better Approaches to FIFA Compliance

Ultimately, using the DOL’s model freelancer contract is probably better than not satisfying the obligation to put the terms of a freelance engagement in writing. However, hiring parties should strongly consider preparing their own agreements (with appropriate legal advice). It’s probably fair to say the DOL’s template is designed to favor freelancers. Even if not, the one-size-fits-all approach is likely to lead to problems down the road for some hiring parties.

Remember, the Freelance Isn’t Free Act and other related employment/independent contractor provisions are intended to protect workers. Any ambiguity will be resolved to their benefit. Thus, it’s critical to be intentional and cautious in drafting your independent contractor agreements (whether subject to FIFA or not).

 

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Happy Employees

Happy Employees Don’t Sue

I’ve been representing companies regarding employment law matters for almost 13 years now. Based on this experience, I want to share an observation. It’s a relatively obvious, simple, and practical one. Yet, I believe it will help many employers if they take it to heart. So, here it is: happy employees seldom make legal trouble for their employers!

There is a staggering number of laws that regulate the employment relationship and work environment. My job is to help organizations follow those laws as well as possible, but perfect compliance probably isn’t feasible. However, substantial compliance is. And that may be sufficient to stay out of trouble as long as you generally treat your employees well.

Unhappy Employees

Most companies have many happy employees. If nothing else, most of them are grateful to be working there. They are either lucky to have a job in the first place (if they have low skills or the economy is bad) or they had job options and chose your company (e.g., marketable skills, good economy). But various circumstances can sour an employee’s mood.

Of course, employers don’t have complete control over their employees’ happiness. Personal, family, and other outside influences play a role in their overall attitude, demeanor, perspective, etc. But the employees’ feelings about their job go a long way in determining how likely they are to bring a claim against the company.

Employee A

Take the case of Employee A. She is a productive office worker who has been with the company for five years. She has received regular salary bumps each year and likes her co-workers.

Employee A has two young children at home. One day she asks for the afternoon off to go to a school function. Her boss says no without any good reason. Being a good employee, she stays at work and luckily her husband can attend the school event that day. The same situation arises a few more times over the school year. Then, one day, Employee A learns from a co-worker that their company was misclassifying them as exempt, such that Employee A (among others) should have been receiving overtime (in her case since she started working there).

Employee A is a generally happy person, but hasn’t liked missing her children’s events. She is particularly frustrated that she never received an explanation for why she had to work. In her mind, the office would have been fine those few afternoons without her. We wouldn’t be shocked if Employee A now takes out that frustration on her employer by calling the Department of Labor or an attorney to complain about unpaid overtime, would we?

Employee B

Now let’s consider Employee B. He’s a part-time employee in his 60s. He just joined the company last year. He doesn’t talk much, but gets his job (data entry) done accurately.

A new, much younger, female employee asks Employee B to lunch one day. Surprised by the sudden invitation, he declines, but agrees to eat with her another day. She asks again the following week, and he confesses that he’s not sure his wife would like it if he went to lunch with her alone. The woman finds this shocking and complains to management. The next day Employee B’s boss tells him he must eat lunch with the other employee or else he could get in trouble for violating the company’s anti-harassment policy. Employee B explains that it would make him very uncomfortable, but the boss persists.

Employee B relents and goes out to a local restaurant with the younger co-worker. They eat, make small talk about their jobs, and return to work.

The next week, the young woman tells co-workers that Employee B is dull and old school. She says she tried to be nice and get to know him out of pity for “the old man,” but that he’s so miserable, she’s sorry she tried. Hearing about what she was saying, Employee B asked his boss to look into it. The boss just told him he needs to be friendlier and people won’t complain about him.

A month later, Employee B applies for a full-time opening with the company. He doesn’t get the position. His boss tells him that the (younger) person promoted was more qualified because he (unlike Employee B) had graduated college. Under these circumstances, would we expect Employee B to accept that explanation? Even if he really should have been more personable at work, the way his boss treated him probably increases the chance that he would file an age discrimination claim against the company.

Happy Employees

Now let’s change the two scenarios above to show how better managers may have handled them. Subtle shifts in approach could yield substantially different outcomes.

Employee A

Remember the mom who wanted the afternoon off to go to her children’s school? Suppose her boss had allowed her to use vacation time to take a half day the first time she asked, but noted that the company may not always be able to accommodate these requests. The boss perhaps added that more notice would be helpful in the future.

Over time, the employee makes similar requests. Sometimes she is excused from work. Other times her manager explains that it would be a hardship on the company for her to take the time off. And, ideally, the boss gives a logical reason for denying the time off on each occasion.

Now when Employee A learns that the company had made a mistake in treating her as exempt, she doesn’t rush to the Department of Labor or encourage other employees to do so. Instead, she meets with her boss to discuss the matter. She is satisfied to hear that the company will pay her for overtime worked over the past year and will raise her pay going forward so that she properly meets the exemption requirements. Yes, this still costs the company more, but it is less than what the employee might have demanded under applicable laws. Still, Employee A is happy because she has been treated humanely in the past and accepts that the company is trying to balance its needs and hers.

Employee B

Now, what should have happened when Employee B declined his younger co-worker’s lunch invitation? We’ll make some small changes in that scenario in hopes of a better outcome.

Instead of ordering Employee B to have lunch with the female co-worker, his boss could have arranged a team lunch. He could have explained to Employee B that it may be a good idea for him to interact more with co-workers and that this may be a good opportunity to “break the ice.” Employee B agrees that he’s open to being more friendly at work, but didn’t want to be taken the wrong way or to accidentally offend anyone.

The lunch goes off fine. Employee B interacts with the co-worker who originally invited him to lunch among others. Nothing inappropriate or remarkable transpired. Nonetheless, the young woman still complains about Employee B to other employees, including references about his age. When Employee B reports this to his boss, he is asked to ignore it and just try to develop better relationships with other employees for now. The boss adds that he knows she shouldn’t be saying these things, but that she is brilliant in her field and, frankly, just not that good with interpersonal relationships.

Later when Employee B does not get the promotion, the boss again explains that younger person who received the full-time position has better credentials, but that the company will be happy to consider Employee B for openings in the future. Even though Employee B’s boss probably should have taken further action regarding the co-worker’s negative comments, Employee B feels like his manager is listening to him, and they’re more or less on the same page. So he doesn’t gripe about being passed over and keeps working hard so he can pursue the next opportunity that arises.

What’s Different?

What’s fundamentally different about the happy and unhappy employees in these scenarios? The happy employees feel their managers respect them as people. They don’t always see eye-to-eye, but the employees’ feelings are at least weighed before decisions are made.

We can’t actually say which of these employees are “happy” or “unhappy” in the big picture. We’re looking at a relative feeling about their jobs. The point here is not that companies should always do what their employees want in every situation. That wouldn’t work in the long run and would end up alienating many employees (like the ones who are not comfortable asking for what they want). But companies, through management, can and should demonstrate a commitment to respect and a pursuit of fairness. Most employees–at least, good ones–perceive those qualities and thrive off of them.

Don’t Take This Too Far

When I say happy employees don’t sue, it’s not a guarantee. You can treat someone well 100 times and then cross the line once to your peril. People can more easily forgive some transgressions than others (e.g., payroll errors vs. sexual harassment). And some people are just harder to please.

But in my experience representing employers, how employees generally feel about their jobs, co-workers, managers, and the organization is usually relevant in weighing risks of grievances, administrative charges, litigation, etc. It just makes sense that treating people well is better for business overall.

Takeaways

Employment law compliance is a monumental task that grows more complex with larger workplaces. However, it doesn’t take much employment law expertise to try to do the right thing.

Employers who focus solely on the bare minimum they can get away with legally are probably more apt to make compliance mistakes. Or at least to be taken to task for those mistakes.

Conversely, employers who focus on treating employees with respect can probably get away with more technical errors or even complete misapplication (or inapplication) of the laws.

But, not surprisingly, organizations with the strongest commitment to showing respect to their employees often do the best job at legal compliance. And they usually have happy employees.

 

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