Thirteen states currently have some form of state-mandated leave.

That’s over a quarter of the country, and the list keeps growing. But don’t let the number fool you, each of those 13 has its own rules, requirements, timelines, and definitions. And to make it extra fun, none of the states are consistent with each other and change year-to-year.

“There are tens of thousands of different leave combinations,” said Jen Henderson, Founder and CEO of Tilt, in a recent conversation with Bereave CEO Justin Clifford. “So we are continually flabbergasted as to how many big companies manage leave in spreadsheets, or whiteboards, or any 1995 tool you want to throw at it. It’s become completely untenable.”

Consider a situation where your team is based in Indiana, but you’re managing leave for an employee in California. Suddenly, you’re fielding questions about job protection, partial wage replacement, documentation requirements, and overlapping eligibility, all under California’s notoriously complex web of leave laws.

Meanwhile, the leave itself may evolve. What starts as a mental health leave could shift into caregiving, or bereavement, or both.

If you’re using a spreadsheet or cobbled-together workflow, every twist in that leave journey becomes a potential compliance misstep.

And here’s the kicker: this isn’t static. “It’s such a dynamic space,” Henderson explains. HR teams are “having to comb the legal updates and they’re having to stay up to date on these changes.”

For Corey Glover, People Operations Analyst at Varo Bank, managing employee leaves of absence is about building trust through open communication and creating a supportive experience for employees during critical life moments.

“When I joined here almost three years ago, leave management wasn’t working exactly how I envisioned it,” Corey explains. By leveraging Tilt and implementing a transparent, employee-focused approach, Corey is staying ahead of the curve with the evolution of leave management, and has transformed the entire process at Varo into a seamless process that supports both employees and the business.

On paper (or in that Excel file you’ve been nursing since 2019), things might seem organized. But in reality, fragmented tools wreak havoc on HR operations.

Raise your hand if you’ve ever had this inner dialogue…“Is the employee actually starting leave when they told me they would? And where did I jot that note down? Is it on the sticky note that’s on my screen in front of me? Is it on my phone somewhere? An email thread?”

Sound familiar? You’re not alone. Also, you can put your hand down.

• When leave management is decentralized, every update becomes a potential point of failure:
• A changed surgery date means editing three calendars and sending four emails.
• A miscalculated return date means adjusting payroll (again) and explaining the mistake (again).
• A manager never got the update because the HR partner forgot to CC them.

“Those leave dates have changed. And so now you have to go across multiple different systems to be supporting that,” explains Brad Hyland, Director of Leave and Customer Success at Tilt.

Even if you’re used to the chaos, you shouldn’t have to normalize it. Because it’s not just inefficient, it’s risky.

Managers typically don’t intend to mishandle leave, they’re simply trying to manage their priorities with limited bandwidth. Allison Whalen, CEO of Parentaly, shared in a recent panel discussion:

“For the person going on leave because they’re expanding their family, this is their number one priority. For the manager, it’s like number 19 on their list. It’s never going to be number one. And so even good managers, they’re just never going to spend all the time figuring out how to be an expert in handling this thing that happens once or twice every few years to them.”

Leave management is inherently complex, highly personal, and unpredictable. Few managers ever gain proficiency in it. Without access to real-time information—like leave timelines, transition plans, or key policy milestones—they’re left to guess.

This guesswork has immediate consequences: Managers repeatedly contact HR for basic details, or they make decisions that contradict policy. Jessica Winder, SVP of People at CoLab, notes:

“HR can enact all the policies they want. If the manager is saying, we don’t care what the policy says, we’re going to do X, Y, and Z, the culture is going to flatline.”

They say knowledge is power, but ask the same “they” about the world of leave of absence and they’ll tell you that the lack of knowledge is costly. Take, for example, not having insight into upcoming leaves of absence across your organization.

“You might not know that a specific employee is even out of the office at any given moment,” said Brad Hyland, VP of Leave and Customer Success at Tilt. In a remote or hybrid work world, the consequences of that statement are big.
If someone is unexpectedly out and you don’t have proper coverage lined up, the rest of the team is left to pick up the slack, or worse, key business operations grind to a halt.

And when outdated leave data collides with a payroll cycle? Hyland warns, “If we’re coming up to something like a specific end of pay period… that could result in a massive change in that person’s pay… [they] may end up with that employee being drastically overpaid or potentially underpaid.”

Now layer on compliance risks, leave tracking errors, and the very real possibility of someone missing an application window for job protection or state benefits. What might feel like a calendar oversight turns into a potential legal issue and a human experience gone wrong.

Disconnected HR and payroll solutions usually mean someone is stuck doing heaps of manual data entry, cross-checking systems, or fixing mistakes. And let’s be honest, that “someone” is usually you or your already stretched-thin HR team.

Leave management had always been part of the job, but for this Sr. Manager of Total Rewards, it didn’t stay simple for long. “A handful of leaves can be managed relatively easily,” she said,
“but as volume increases there are employees in different leave stages and keeping on top of the process becomes very difficult.

As employee headcount and geographic spread increased, the systems in place struggled to keep up under the weight of complexity. “Multiple leaves happening simultaneously in various states” had become the norm, and the team found that a few cases were manageable, but the moment volume picked up, visibility and consistency was hard to come by.

The biggest challenge? Keeping up with different state laws and leave programs, and trying to maintain accuracy as employees moved through different leave stages. “Keeping on top of the process becomes very difficult,” they explained. The team was also dealing with a frequent issue where employees simply didn’t know they needed to apply for state or short-term disability benefits leading to delays, stress, and lots of cleanup on the backend.

As FluentStream expanded across more than 20 states, so did the complexity of managing employee leave. For Allie Morton, Director of People Operations, keeping pace with evolving laws and creating compliant leave plans manually was becoming increasingly difficult. She and a payroll specialist handled each new leave request by hand, researching regulations, customizing plans, and hoping nothing slipped through the cracks.

The process was time-consuming and pressure-filled, and as the company grew, so did the demands. Managing leave without automation or built-in compliance safeguards turned even simple requests into time-intensive tasks. Allie describes how, at one point, “staying on top of the various leave laws was nearly impossible,” and the worry became a constant companion.

But the challenges were also a turning point.

FluentStream recognized that modernizing their leave management wasn’t just about reducing the burden, it was about creating a better, more scalable experience for everyone involved.