Chaim Book, a senior partner at Book Law LLP, has spent years navigating the complex intersection of workplace productivity and disability law. He has become a leading voice on how organizations can protect themselves while genuinely supporting employees dealing with mental health challenges and chronic illnesses. In this discussion, he sheds light on why the most dangerous thing a manager can do is make a snap decision without a paper trail, especially as mental health awareness transforms the modern workplace.
The conversation delves into the legal requirements of the interactive process, moving beyond simple approvals or denials of leave. We examine the rise of invisible disabilities like anxiety and long-term cognitive fatigue, the importance of distinguishing essential job functions from entrenched workplace habits, and the critical role of contemporaneous documentation and respect in mitigating litigation risks.
Many managers view a request for mental health leave as a simple binary choice between saying yes or no. Why is this perspective so dangerous for an organization’s legal standing?
The instinct to provide a quick answer, whether it is a “yes” to avoid conflict or a “no” out of frustration, is precisely what puts employers in a vulnerable position. When a manager improvises a decision, they are often skipping the “interactive process,” which the Americans with Disabilities Act treats not as a suggestion, but as the substance of the legal duty itself. I have seen cases where an employer reached a perfectly defensible outcome on the merits, yet they were still held liable because they failed to demonstrate a genuine exchange with the employee. The law doesn’t just demand the right result; it demands a visible, documented effort to explore how the employee can still perform their role. By jumping straight to a conclusion, the employer loses the opportunity to define the boundaries of the job, often resulting in costly legal fees and unnecessary liability.
We are seeing a significant increase in disclosures regarding invisible conditions like chronic illness or cognitive fatigue. How should managers shift their approach when there is no visible trace of a disability?
It is a sign of progress that employees now feel more comfortable disclosing conditions like anxiety or the lingering fatigue that follows a serious infection, but it creates a new challenge for untrained managers. When a condition isn’t as obvious as a broken leg, the employer is entitled to start by asking the employee to substantiate the condition through medical documentation. This is a step many managers avoid because they feel it is an intrusion of privacy, but it is a vital part of the discovery process. You have to ask the basic question: with this condition, and with or without an accommodation, can this person actually do the job? If you don’t establish that baseline, you are essentially flying blind, making decisions based on assumptions rather than medical facts or business needs.
If an employee asks for a specific schedule change, such as taking every Tuesday off for mental health, what steps should the interactive process involve?
The first step is determining if the request interferes with the “essential functions” of the role rather than just disrupting entrenched habits. For instance, if that employee is responsible for leading a standing client meeting every Tuesday, you have to honestly evaluate whether that meeting can be moved or if another person can cover it without causing an undue burden. This inquiry is often uncomfortable and unhurried, which is exactly why managers try to take shortcuts that later get dismantled by a plaintiff’s lawyer. You aren’t looking for an automatic “yes” or “no”; you are looking to see if there is a middle ground or an alternative accommodation that keeps the business running. If the conclusion is that the Tuesday absence is not reasonable, the conversation doesn’t end there—you must still consider if a different accommodation could address the medical need.
What are the long-term risks of a “reflexive agreement,” where a manager simply grants an open-ended request to avoid a confrontation?
Reflexive agreement carries a hidden cost that can haunt a company for years. By granting an open-ended request without first defining what the job demands, you might quietly relieve an employee of the core responsibilities of their role without even realizing it. A year down the line, when the rest of the team is burnt out from absorbing the extra work, reversing that arrangement becomes incredibly difficult because you’ve set a precedent. There will be no record that the change was intended to be temporary or that it was a deviation from the essential functions of the position. It is much harder to fix a poorly planned “yes” after 12 months than it would have been to have a structured, difficult conversation at the very beginning.
When these disputes reach the EEOC or state commissions, what specific evidence determines whether an employer acted in good faith?
When a case reaches the U.S. Equal Employment Opportunity Commission or the New York State Division of Human Rights, the focus shifts quickly from what the employer decided to how they reached that decision. I have watched many defensible positions collapse simply because the entire history of the request lived in corridor conversations and a handful of scattered text messages. Without a contemporaneous record or a second person present during key meetings, an employer is left to litigate from memory against an adversary who has likely rehearsed their version of events many times. You must be able to show, in writing, that you received the request, weighed it against the job’s requirements, and had a logical reason for your conclusion. A brief, written acknowledgment of the request can outlast every human recollection when you are standing in front of a commission.
Beyond the legal documentation and the technicalities of the ADA, how much does the emotional tone of these interactions impact the likelihood of a lawsuit?
One of the most overlooked aspects of employment law is that people who believe they were treated with respect and fairness seldom go looking for a lawyer. Even if the ultimate decision is a termination or a denial of a specific request, the way that news is delivered matters immensely. If an employee feels heard and sees that the company actually engaged with their struggle, they are far less likely to seek out a sympathetic audience in a courtroom. However, when a manager is dismissive or treats an accommodation request as a nuisance to be “closed out,” it creates a sense of grievance that drives people to litigate. An accommodation request isn’t just a problem to be solved; it’s a moment where the law expects you to treat the employee as a partner in a shared, transparent process.
What is your forecast for how mental health accommodations will evolve in the workplace over the next few years?
From 2026 to 2028, we will see a much sharper focus on “cognitive load” as a standardized metric for reasonable accommodations. As remote work and flexible schedules remain the norm, the legal battleground will shift from physical presence to the specific timing and intensity of tasks. Employers will need to become much more sophisticated in how they document job descriptions, moving away from generic templates to hyper-specific lists of essential functions. Organizations that fail to train their mid-level managers on the nuances of the interactive process today will likely find themselves overwhelmed by litigation as mental health disclosures continue to rise. The companies that thrive will be those that view these requests not as legal threats, but as a formal decision-making process that must be conducted in the open and on the record.