1. The biggest mistake companies make: treating leave like a checklist

Many HR teams approach leave management like a compliance exercise: fill out forms, send the PDFs, check the boxes. But that approach misses the reality of what employees are actually going through.

Leave only happens during major life moments — welcoming a child, caring for family, grieving a loss, or navigating a health issue. The experience needs to meet people where they are emotionally and operationally.

Kim explained that employees show up to leave in very different ways. Some want every detail up front, while others feel overwhelmed by too much information and just want to know the next step.

“Some people say, ‘Give me every piece of information you have.’ Others say, ‘Just tell me what I need to do right now.’”

Great leave programs don’t assume one experience works for everyone. They’re designed to flex depending on what the employee actually needs.

2. There are two types of employees taking leave — and both need different support

After supporting hundreds of leave cases, Kim has noticed a consistent pattern: employees usually fall into two camps.

The first group wants maximum information and control. They want the policies, timelines, paperwork, and benefits breakdown immediately so they can plan everything ahead of time.

The second group prefers minimal information at the start. Too many documents or policies can feel overwhelming when they’re already dealing with a big life event.

“Some people are really high-touch. Some people are really low-touch. And how you show up determines whether they feel supported.”

This is where many leave processes fail. Companies deliver the exact same experience to everyone — usually a giant PDF packet.

Instead, modern leave programs adapt communication styles based on the employee’s needs.

3. The most important leave conversation happens before someone leaves

One of the hardest moments in any leave process is preparing the knowledge transfer and coverage plan.

Employees often hesitate to write down everything they do. It can trigger a fear many people have but rarely say out loud: What if they realize they don’t need me?

Kim experienced this firsthand before her own parental leave.

“I told my leader, ‘I’ve been avoiding this conversation. I don’t want to write down how to do my job.’”

What changed the experience was the framing.

Instead of positioning the coverage plan as a replacement exercise, leadership framed it as a way to ensure she could fully disconnect and enjoy her leave without being pulled back into work.

That mindset shift allowed her to invest deeply in the handoff — and ultimately made her leave far more successful.

4. Managers play a bigger role in leave than most HR teams realize

Leave management is often seen as an HR responsibility. But the employee’s direct manager is one of the most important stakeholders in the entire process.

Managers are responsible for:

• Creating the coverage plan
• Managing team expectations
• Supporting the employee before and after leave
• Helping them reintegrate when they return

But many managers feel unprepared for these conversations.

Kim’s advice is simple: equip them with clear resources.

For example, her team created a knowledge transfer template managers can use with employees to document:

• Projects currently in flight
• Key responsibilities
• What can pause during leave
• What must continue

This turns a stressful handoff into a structured conversation.

“It’s really a knowledge dump so the manager can start creating a coverage plan.”

5. When employees return, don’t overwhelm them — give them the “Rule of Five”

Coming back from leave can feel just as disorienting as preparing for it.

Employees often worry they’ve missed everything — new goals, team changes, product updates, company announcements.

But dumping weeks or months of updates on someone isn’t helpful.

Kim recommends a simple framework: the Rule of Five.

When someone returns, share the 3–5 most important updates they need to understand the current state of the company.

Examples might include:

• Key team or leadership changes
• The latest company goals or strategy
• Major product or business updates
• Important announcements or recordings

“Give them enough context to understand what’s changed without sending months of backlog.”

It’s a fast way to get someone oriented without overwhelming them.

6. The real “cheat code” for great leave programs: combine technology with human support

One reason leave feels so overwhelming for HR teams is the sheer number of moving parts:

• Company leave policies
• State benefits
• Short-term disability
• Documentation requirements
• Return-to-work planning

Trying to manage all of that manually often leads to spreadsheets, folders, and scattered communication.

Kim’s perspective: technology should handle the operational complexity so HR can focus on supporting employees.

“The technology is doing the work. I’m reviewing it and supporting the employee.”

At the same time, tools like AI can help HR teams communicate more clearly — whether that’s summarizing leave instructions or identifying where employees might get confused.

The goal isn’t to remove the human element.

It’s to free HR up to show up where it matters most.

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