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Earlier this month, Disclo’s co-founder Hannah Olson spoke at the DMEC Annual Conference about a shift nearly every leave and accommodations professional is beginning to experience: Gen Z is changing not only what employees expect from work, but how they understand their rights, advocate for support, and navigate workplace accommodation processes.
Her session centered on a simple reframe: many of the behaviors employers are quick to label as “difficult” may be better understood as "different", the result of a generation entering the workforce with an entirely different set of experiences, tools, and expectations.
The conversation generated enough discussion that we knew it shouldn’t live only with the people who happened to be in the room.
Much of the conversation about Gen Z at work has focused on values: flexibility, purpose, boundaries, mental health, and expectations around work-life balance. Those differences matter. But for employers responsible for disability, leave, and accommodations, there is a more structural change underway.
Gen Z is entering the workforce with a level of familiarity with accommodations, self-advocacy, digital research, and AI-assisted communication that previous generations simply did not have at the same age. Behaviors that can initially read as confrontational, overly sophisticated, or even suspicious are often better understood as the product of a fundamentally different experience.
That distinction matters. “Difficult” is a label. “Different” is something employers can design for.
This is not a future workforce trend. Gen Z has already overtaken Baby Boomers as a share of the U.S. workforce, and the Bureau of Labor Statistics projections estimate that the generation will represent roughly 30% of the workforce by 2030.
More important than the demographic shift, though, is what many younger employees experienced before they ever entered the workplace.
Approximately 15% of U.S. public-school students are served under the Individuals with Disabilities Education Act through an Individualized Education Program, or IEP. Add students receiving accommodations through Section 504 plans, and more than one in five students may reach the end of high school having experienced some form of formal, documented support.
For previous generations, requesting a workplace accommodation was often an unfamiliar experience. Employees likely spent years managing a condition privately before approaching HR, and disclosing a disability often felt intimidating or deeply personal.
For a meaningful portion of Gen Z, the concept itself is far less novel. They may have spent years participating in conversations about what they need to succeed, providing documentation, reviewing written accommodation plans, and working with teachers, counselors, disability professionals, or parents to adjust those plans over time.
That experience often continues in college, where responsibility uniquely shifts to the student. Unlike K–12 education, students generally must self-identify themselves, register with the disability services office, provide documentation, and advocate for specific support. The share of college students reporting a disability has doubled in recent years, with mental health conditions and ADHD accounting for much of that growth.
By the time many of those students enter the workforce, self-advocacy isn’t a brand-new skill. They’ve already practiced gathering documentation, articulating limitations, and asking an institution to make an adjustment.
That context should change how employers interpret a sophisticated entry-level request. An employee who cites the ADA, clearly articulates functional limitations, or asks for a specific modification may not be unusually litigious or coached. They may simply be applying skills they have used since high school or college.
The information environment has changed just as significantly.
For many younger employees, HR is no longer the first stop when they have a workplace question. By the time an accommodation request reaches an employer, the employee may have already scoured the internet, watched employment attorneys on TikTok, dug through Reddit threads, compared other workers’ experiences, and asked an AI tool to help draft the request to their employer.
A 2025 survey cited in the presentation found that 92% of Gen Z respondents trusted TikTok for career advice. At the same time, 55% said they had followed workplace advice that later turned out to be misleading.
That creates a new dynamic for employers: employees may arrive highly informed about the process, but not necessarily accurately informed about every rule. They may already have legal vocabulary, documentation, a specific outcome in mind, and a rehearsed explanation for why they believe they are entitled to it.
Generative AI adds another layer. An employee can ask an AI tool to draft an accommodation request and receive a polished letter in seconds, complete with terms like “reasonable accommodation,” references to the ADA, and suggestions for potential accommodations. The result is that employers are beginning to see requests with remarkably similar phrasing and structure.
That sameness can trigger skepticism. A team may assume an employee has been coached, that multiple employees are coordinating, or that someone is deliberately constructing a legal record.
Often, the explanation is simpler: millions of employees have access to the same tools and are asking them similar questions.
The employer’s job isn’t to grade the prose or determine which sentences came from a chatbot. It’s to understand the underlying need, gather appropriate information, engage in an individualized conversation, and evaluate the request on its merits.
There’s also an opportunity here. If employees can find detailed explanations of workplace rights from a stranger on social media but cannot easily find a clear explanation of their own employer’s accommodation process, the organization has left an information vacuum. Employers may never out-post TikTok, but they can become the more trustworthy and relevant source.
The substance of workplace accommodation requests is evolving alongside the way they’re submitted.
Gen Z reports high levels of anxiety and greater engagement with mental health care than previous generations. Gallup data found that approximately 47% of Gen Z often or always feel anxious, while roughly 39% report having worked with a mental health professional.
For employers, prevalence is only part of the story. Willingness to disclose matters just as much.
Many traditional accommodation processes were built around an implicit assumption that employees would be reluctant to disclose a disability, particularly an invisible or psychological condition. That assumption shaped everything from intake design to communication practices and staffing models.
It’s becoming less reliable.
Younger employees are often more accustomed to discussing mental health, more familiar with accommodations, and more willing to formally ask for support. At the same time, priorities commonly associated with Gen Z (such as flexibility, autonomy, transparency, mental health support, and work-life balance) offer a useful preview of the kinds of requests employers may see more frequently. The presentation specifically highlighted an expected shift toward requests involving flexible schedules, remote work, and invisible, episodic, or psychological conditions.
Those cases can also be more operationally complex, particularly when an employee’s needs implicate multiple frameworks at once, such as the ADA, FMLA, the Pregnant Workers Fairness Act, and state paid leave programs.
This is where generational misunderstanding can become an operational and compliance problem.
Consider an employee who cites the ADA by name, submits a highly polished request, pushes back when asked for medical information they believe is unnecessary, and discusses the experience publicly online.
Through one lens, those behaviors may look litigious, coached, evasive, or threatening.
Through another, the same employee may simply be process-literate, may have used the same AI tool as everyone else, may have researched the limits of permissible documentation, and may communicate publicly because that is how they communicate about much of their life.
The facts have not changed. Only the interpretation has.
Disclo’s CEO, Hannah, described this as the difference between reading an employee as “difficult” and reading them as “different.” A templated request may reflect widespread use of free AI, not coordination. Pushback on documentation may reflect familiarity with what information an employer can appropriately request. Familiarity with legal terminology may simply mean the employee has done their homework.
That distinction matters because labels influence behavior. Once an employee has been informally categorized as “difficult,” teams may unintentionally begin handling the case differently: asking for additional documentation, responding more slowly, granting less benefit of the doubt, or approaching every interaction defensively.
At scale, those subtle differences create inconsistent processes. And inconsistency in an accommodation program is not merely an employee-experience problem; it can become an equity and compliance problem as well.
One of the most important disciplines employers can build, particularly at the manager level, is the ability to separate an employee’s behavior from the merits of the request. The tone, sophistication, or source of a request does not determine whether it is valid.
Taken together, these shifts create four related pressures for employers: volume, documentation, complexity, and compliance.
There is an important irony in all of this: many of the expectations creating pressure on accommodation teams were shaped by technology, and technology can also help employers meet them.
Employees are accustomed to digital experiences that are available on demand, provide immediate confirmation, and make status visible. Against that backdrop, an accommodation process built around a PDF sent to a shared inbox followed by weeks of silence feels unusually opaque.
Modernizing that experience does not mean automating the human judgment out of accommodations. It means using technology deliberately where it can improve consistency and remove unnecessary administrative friction.
Structured digital intake can make the process accessible whenever an employee needs it. Automated routing can ensure requests reach the appropriate person. Status visibility can reduce the uncertainty that drives follow-up. Standardized workflows can help ensure employees are asked the same lawful questions and routed through the same core process. Automatic audit trails can create reliable documentation without requiring an analyst to manually reconstruct every interaction.
These are the areas where automation genuinely adds value.
The bright line is the determination itself. The interactive process remains individualized. AI can intake, organize, route, summarize, and remind; humans need to own the conversation, exercise judgment, and make the decision.
As Hannah put it: AI can handle the process. Humans need to own the determination.
Perhaps the most useful conclusion from the conversation at DMEC is that employers don’t have to choose between meeting the expectations of a younger workforce and protecting the organization.
In many respects, the two goals have converged.
The three qualities that make an accommodation program more defensible (consistency, transparency, and documentation) are also qualities this generation increasingly expects from the organizations they work for.
Those are compliance disciplines, but they are also experience disciplines. A program that does them well is easier to administer, easier to defend, and easier for employees to trust.
Organizations do not need to redesign their accommodation programs around a single generation. But the behaviors highlighted above offer a useful stress test for whether existing processes are ready for the workforce they are meant to serve.
Gen Z will continue to expose gaps between accommodation policies as they are written and processes as employees actually experience them. That does not have to be viewed as a threat. It can also be useful feedback about where programs have failed to keep pace.
The employers best positioned for the next decade will not be the ones that figure out how to manage a supposedly “difficult” generation. They will be the ones that recognize what has changed and build accordingly.
That is, in many ways, what Disclo has been building for from the beginning: a workplace accommodation experience designed for a workforce that expects clarity, accessibility, consistency, and transparency — without sacrificing the structure and defensibility employers need.
They’re not difficult. They’re different. At Disclo, we’re building for different.
