Rethinking Leave Management for a Human-Centered Workplace
Let’s start with a hard truth: leave management is messy.
Too often, it’s seen as a compliance headache or an administrative checkbox. Something HR is required by law to manage, but nobody wants to discuss or deal with.
But more HR leaders are realizing that ignoring the way leave is managed isn’t just risky, it’s damaging to employees, to business success, and to company culture.
Tilt recently held a live panel discussion with experts who live and breathe leave of absence and the consensus was clear:
The system is broken. And it’s time we fixed it.
Moderated by Daniel and Stephen Huerta from Modern People Leader, Tilt’s Founder and CEO Jen Henderson was joined by Justin Clifford, CEO of Bereave, Allison Whalen, CEO of Parentaly, and Jessica Winder, SVP of People at CoLab to talk about exactly that.
If you didn’t get a chance to watch the incredible discussion, you can watch it on demand here.
Below are the 5 main takeaways you might have missed.
1. Leave Management Is More Than Just Checking the Compliance Box
While compliance remains a foundational element of any leave program, it’s only one element of a complicated process.
Navigating evolving laws and state-specific requirements can be complex even for the most diligent HR teams, but the true impact lies beyond legal line items.
Focusing solely on regulations overlooks two equally vital dimensions: maintaining business and career continuity, and honoring the personal, often emotional, life events that prompt a leave. Common events such as welcoming a child, managing a health challenge, or caring for a loved one only scratch the surface.
These pivotal moments in an employee’s life deserve more than administrative efficiency.
“It’s bigger than ‘approve this leave and then just come back to work,’” says Jessica, “so think about it as a whole-person experience, not just here’s your leave and come back whenever you’re ready.”
When organizations reframe leave from a compliance obligation to a human-centered experience, they create space for empathy, stability, and long-term engagement—at the moments it matters most.
2. The Manager-Employee Relationship Shapes the Leave Experience
Managers are the linchpin of the leave experience. but they’re often left without the tools, training, or support to navigate it well.
One story during the discussion made this clear: a woman returning from bereavement leave was met with well-meaning but painful questions about how her “vacation” went. The absence of manager preparation and team communication turned an already difficult moment into a distressing one.
Managers don’t need to be legal experts, but they do need support and partnership from HR.
“The best and most incredible HR leaders in the world still need the partnership of those people leaders and managers, especially in the world of leave,” says Jen.
With the right language, checklists, and clarity, they can confidently navigate sensitive moments with care and professionalism. Justin rightly explained that you can’t SOP grief, but you can SOP the considerations when someone is grieving.
Educating and empowering managers this way transforms them from bystanders into allies, and ensures employees feel respected and understood at every step.
3. Proactive Communication Turns Benefits Into Impact
One of the most persistent challenges in today’s workplace is also one of the simplest to solve: employees often don’t know what benefits are available to them.
This lack of awareness isn’t just unfortunate, it can be seriously costly. Organizations invest significant time and resources into building comprehensive benefits packages, but if employees can’t easily access or understand them, the value is lost on both sides.
The solution lies in proactive, ongoing communication. Benefits shouldn’t be something employees stumble upon digging through an intranet or during onboarding, they should be embedded into the rhythm of everyday work life. Companies seeing the highest engagement are the ones taking intentional steps to bring benefits to the forefront.
Some effective tactics include:
- Weekly “Did You Know?” Slack messages that highlight timely or underused benefits
- Email signatures that link directly to leave policies or Employee Assistance Programs (EAPs)
- Equipping managers with easy-to-use benefit FAQs so they can confidently guide their teams
These small, consistent actions add up. When employees are reminded of their benefits in relevant and accessible ways, they’re more likely to engage with them. And when employees feel supported, the organization benefits too through higher morale, improved retention, and a culture that values well-being.
In short, benefits are only as powerful as the communication strategies behind them. Make them visible, make them clear, and most importantly, make them part of the everyday employee experience.
4. Performance Reviews and Compensation Deserve Intentionality
Leave shouldn’t derail someone’s career, but too often, it does. Despite the best of intentions, outdated processes and unclear policies can unintentionally penalize employees who take necessary time away, particularly during performance review and compensation cycles.
As Allison, puts it, “I would encourage people to think about how to handle performance reviews. You have to explicitly teach managers how to evaluate someone if they’ve been gone six months out of the 12-month period.”
Without clear guidance, managers are left to navigate these situations on their own, often leading to inconsistent or unfair outcomes.
There is also the persistent equity issue: employees returning from leave are sometimes excluded from review cycles altogether, or evaluated unfairly while they’re still ramping back up. Allison referred to this imbalance as the “motherhood penalty” and the “fatherhood bonus.” A reflection of how unconscious bias and outdated frameworks can create unintended disparities.
Closing this gap requires more than good intentions, it requires structure. Forward-thinking organizations are taking steps to ensure fairness and transparency by:
- Encouraging pre-leave self-assessments and peer feedback to preserve performance insights
- Setting clear performance review timelines that reflect time worked, not time missed
- Auditing compensation models, particularly for variable pay roles, to ensure leave doesn’t result in financial setbacks
These thoughtful practices send a clear message: people are valued not just when they’re at their desk but throughout their entire employee journey. When companies align their review and compensation processes with inclusive, equitable principles, they build a workplace where taking leave doesn’t mean falling behind, it means being supported every step of the way.
5. Preparation and Personalization Transform the Leave Experience
One of the most powerful themes to emerge from this conversation is that leave moments are emotional multipliers. How a company shows up during these deeply personal times leaves a lasting impression shaping trust, loyalty, and long-term retention.
Re-onboarding illustrates this perfectly. Often overlooked or treated as a checkbox, it’s actually a key opportunity to rebuild connection. A thoughtful re-entry plan, a warm welcome message, or a dedicated 1:1 with a manager can turn a moment of uncertainty into one of belonging.
Modern leave is not, and should never be, a one-size-fits-all process. Each employee’s circumstances are unique, and their leave experience should reflect that. Early planning, personalization, and consistency are what set great programs apart. This is where the right blend of technology and humanity matters most.
Automation can handle the workflows, documentation, and compliance checkpoints. But the human experience? That can’t be automated. As Jen noted, “Technology can’t replace people, but it can free HR to focus on the people.”
When organizations get this balance right, they send a clear message: every employee matters, not just when they’re working, but throughout their entire journey—including the moments that take them away from work and bring them back again.
The Path Forward: Rethinking Leave as a Strategic Advantage
Leave management doesn’t need another temporary fix, it needs a holistic reimagining. Today’s most resilient organizations recognize that supporting employees during life’s most pivotal moments isn’t just a matter of compliance; it’s a cornerstone of culture, trust, and long-term success.
The path forward calls for a smarter, more human approach. That means:
- Automating compliance to reduce manual risk and free HR teams to focus on people, not paperwork
- Equipping managers with the tools, training, and language to lead with clarity and empathy
- Re-onboarding with intent, turning return-to-work moments into opportunities for connection and care
- Communicating benefits proactively, so employees know what’s available—before they need it
- Treating leave as a human journey, not just a policy to enforce
Because in life’s most vulnerable moments, it’s not a document that shows up, it’s a manager, a teammate, a company’s culture in action.
The organizations that embrace this shift are doing more than checking a box. They’re building loyalty. They’re reinforcing trust. And they’re creating the kind of workplace that stands strong, no matter what life brings next.
Tilt is leading the charge in all things leave of absence management through easy-to-use tech and human touch. Since 2017, our proprietary platform and Empathy Warriors have been helping customers make leave not suck by eliminating administrative burdens, keeping companies compliant, and providing a truly positive and supportive leave of absence experience for their people.
