23 tips (and 2 templates) to support employees through a leave

Even the most seasoned managers have lots of questions and doubts when a direct report takes leave—especially if it’s everybody’s first time. Yet, with over 10,000 leaves taken with Cocoon, we know first hand what it takes to plan a leave well, the questions people tend to have, and the factors that can best improve the employee experience. With Cocoon doing the heavy lifting on compliance, claims, and payroll, People Ops teams and managers can focus their time and attention on supporting an employee through a leave. Here we offer tons of tips, dos and don’ts, and even some templates to help you in the process.

Dos and don’ts upon finding out about an employee’s leave

People usually take leave as a result of a major life event. How you show up in that first conversation is important to get right. Here are some dos and don’ts to set the right tone.

Dos:

• Lead with empathy. Ask how they’re feeling, what their immediate needs and questions are—and truly listen to their answers.
• Keep your emotions in check. Make the leave-taker the protagonist, be steady and supportive for them.
• Show you’re willing to help. A leave-taker might not know what to say or do, and you might not either. Emphasize that you’re willing to learn and help them navigate.
• Lean into privacy and policy. Assume confidentiality with everything they tell you. Refer back to your organization’s leave policies so you understand what’s in scope and tap an HR partner to help you navigate policies in practice.

Don’ts

• Don’t jump in with solutions and advice. You don’t have all the information and answers. At this stage, it’s more important to listen and show your willingness to help them figure it out.
• Don’t make assumptions. Things that seem “happy” or “sad” can be fraught with all kinds of other emotions. Other details about their personal life and factors like race, class, and gender can impact a leave experience in ways you might not fully understand.
• Don’t make comparisons. Your own leave experience may or may not have anything to do with theirs. Your own experience helping another employee through their leave may or may not apply.

How to help a teammate prepare for a leave of absence

Once the wheels are in motion for an employee’s leave, it’s time to proactively plan with them around timelines, workloads, communication preferences, etc. For someone going on parental leave, you likely have a bigger window of time to hash out these details, whereas a medical, caregiver, and other leaves may come on suddenly—do your best to be proactive and to anticipate the unexpected while being reasonable with the time and resources you have.

💡Pro tip: download our leave transition plan worksheet so you can map out a leave plan together in a 1:1. It has a list of questions to work through, with space for your answers. 

1. Make a leave plan and timeline. Our leave options explorer tool is a great way to not only visualize timelines, but to play around with different scenarios to see how policies or pay change along the way. Write down your answers in the planning worksheet.
2. Make sure they feel comfortable and confident using Cocoon. This may sound like a shameless plug, but the biggest questions leave-takers have tend to be around pay and filing claims—and Cocoon is precisely the place where they can file and receive this information accurately, with more help on topics that most managers and even People Ops leads aren’t experts on.
3. Talk about pay and benefits. Though Cocoon has you covered here, it’s still important to discuss. Will any benefits be on hold while they’re out (e.g., stock vesting)? Tap HR, Accounting, and Legal teammates to make sure you’re giving accurate information.
4. Document responsibilities, processes, and current work. Get an idea of their day-to-day and recurring tasks. Understand where projects they’re part of stand. Have them record tutorials to walk colleagues through tools or processes they may be unfamiliar with. 
5. Pass along logins and contacts. What tools do they use that you may need to access or pause the licenses for? Who do they regularly communicate with that you need the contact information of? 
6. Re-balance team workloads. Figure out who can cover what, what you may have to outsource, and what might need to go on hold. Have this discussion in a team meeting for visibility. Nobody wants to feel like they suddenly got work dumped on them or that they were overlooked.
7. Discuss communication preferences. Generally, you shouldn’t contact someone on leave, but it’s important to set boundaries about how and when they might want to be contacted, and for what reasons.

Dos and don’ts while your employee is out on leave

By this stage, the plan you made has shifted into reality. While things don’t always go according to plan… these dos and don’ts keep you going steady on what you can control.

DON’T reach out… DO keep a one-pager of key updates

Though it might feel off to not check in, respect a leave-taker’s time away. Communications from a coworker might make them feel stressed or obligated to respond. Unless they have explicitly contacted you or asked to be contacted, a better way to handle this is by keeping track of team, project, and company updates as they happen and presenting them upon their return. 

💡Pro tip: If you have a regular 1:1 with the leave-taker, instead of canceling it, use that time to work on the updates so you don’t get behind.

DON’T expect them to do work… DO start preparing for their return to work

Except for staying on top of timely claims paperwork (which Cocoon helps with), a leave-taker shouldn’t have anything on their to-do list. Instead, focus on planning for their return from leave. Understand what accommodations your company offers (e.g., schedule modifications) and start to think about handoffs and workload re-balancing. Get your key updates one-pager ready, and refer back to the list of their responsibilities and project work to understand how handoffs could work. 

How to support a colleague after they return from leave 

Whether a leave-taker is ready to return to work or hesitant to, this transition will be a big shift for everyone, especially the leave-taker. Let them set the pace, while being an effective ally to help them set and achieve the boundaries and accommodations they need. Here are some tips for a smooth return:

1. Welcome them back. Make sure the team is aware of the leave-taker’s return date so they feel acknowledged and welcomed—but avoid making it a big spectacle or putting them on the spot.
2. Have an open, real conversation. Find a good time to sit down for a private one-on-one to ask them how things went, how they’re doing and feeling, what they need. Don’t get into work duties and what they missed—focus on their experience and listening.
3. Set ramp-up expectations. A leave-taker might need to set a particular schedule around their hours, or days they work from home vs. in-office. Communication norms should also be set (e.g., video off, no Slacks after 4pm). Loop in an HR partner to discuss additional accommodations, and explore them in Cocoon. 
4. Present the “things you missed” one-pager. Set aside time to go through your list of updates together, and also let them dive in by themselves. Answer any questions they may have.
5. Re-balance workloads. Once a leave-taker is caught up, you can work as a team to determine what will be handed off, when, and how—ensuring the scope and pace of handoffs makes sense.
6. Encourage community and support. Invite them to relevant Employee Resource Groups, Slack channels, or even informal communities within your organization so they can connect with others who can relate to their situation. 

Taking leave is a transformative experience that comes with highs and lows, and there’s no single way to prepare for an employee’s leave because each situation is different. Yet in leading with empathy, having a supportive mentality, and getting organized with Cocoon, you will be in as good of a place as you can be to support a leave-taker. Cocoon is dedicated to helping you do just that by offering the technology that keeps up with the legal and financial requirements, as well as giving tips to help you navigate the emotional side. Doing so is an important part of being a great manager, with lasting impacts that can resonate through a leave-taker’s career and personal life.