How to successfully re-onboard after PTO or leave

Taking time off is an important and necessary part of our working lives. It ensures time to rest and recharge, and can inspire new ideas and fresh perspectives. Not all time off is for going on vacation, of course. People may need time off to look after their physical or mental health, care for a sick family member, or mourn a loss. They may take several months or even a year off in order to welcome a child as a new parent. Whatever the reason for an absence, returning to work can require some adjustment, especially in case of a longer leave.

As Head of Employee Experience at Oyster, as well as a parent and caregiver myself, I care deeply about building a workplace that ensures a healthy balance between one’s personal and professional lives. That means not only encouraging people to take time off (and really disconnect while they’re away), but also putting support structures in place to help them return to work without feeling lost or overwhelmed.

That’s why at Oyster, we have detailed guidelines around handing off work before going on vacation. In addition, I’ve recently introduced and am currently beta-testing a “reboarding” program for people returning from long-term leave, analogous to the experience of onboarding as a new hire. (Shoutout to the PeopleOps team for their brilliant automation work in our new process!)

Here’s what People teams, managers, and employees can do to foster a healthy culture around taking time off and ensure a successful re-onboarding when someone returns.

Supporting and empowering people to take leave

First, it’s important for employees to feel supported both emotionally and logistically so that they feel comfortable taking time off, whether it’s PTO or long-term leave. They should be able to trust that their manager and teammates will cover them, and that it’s okay to step away and disconnect.

In the case of extended time off, managers can support employees by initiating the conversation, which reassures them that their manager is actively paying attention and looking out for them. Similarly, People teams can normalize taking leave by creating supportive policies and practices, as well as providing templates, guidelines, and real-life examples. Providing the infrastructure helps employees feel empowered to take long-term leave because they know it’s officially available to them and considered a normal part of company operations.

Don’t forget about the power of setting an example—it’s important for leaders at all levels to model the behavior their policies intend to support.

Planning and preparing for leave—especially parental leave

 In order to set yourself up for success, it’s vital to prepare ahead of time, especially when you’ll be away for more than a few weeks. This means planning and documenting who will cover which parts of your work, which projects will be paused until you return, and which items you’d like to be updated on while you’re away. By planning a good handoff process with the help of your manager, and having open conversations with your teammates and other stakeholders, you essentially close those mental loops, which eases anxiety because your brain knows it’s safe to put the work aside.

Preparing for extended leave can be particularly daunting for those going on parental leave because, in addition to the normal anxieties around handing away your work, you’re also planning for a major disruption to your life that will be challenging and exhausting even in the best of circumstances. It can be scary to think about taking that much time off, knowing you’ll probably come back to a different environment than the one you left. And that’s to say nothing of all the unknowns involved in welcoming a new child!

That’s why it’s even more important to think carefully about what kind of leave you want to take and be very detailed and explicit in your planning. For instance, do you want to be completely disconnected from work while you’re out? Do you want a weekly team update from your manager? Do you want to be updated only on certain projects or in specific situations? By having clear expectations in place, you can focus on your new life as a parent, trusting that your manager will either reach out or leave you alone as requested (and knowing  that it’s also okay to change your mind about it later).

Finally, if you’re the person giving birth, it’s best to gradually ramp down during your last few weeks before going on leave. Working full-steam until the last possible moment isn’t necessarily best for you, or for your team (you never know when a baby will arrive early, or you just may want to take a little space between working and childbirth). It’s better to wind down bit by bit, so that by the time you leave, your work is fully handed off and you’re mostly just supporting the people who are taking over for you. This ensures a much smoother transition by allowing sufficient time to get your team set up for success, and to say your temporary goodbyes.

Before you go:

1. Create your handoff document in conversation with your manager and team.
2. Notify colleagues and collaborators of new project contacts and procedures.
3. Agree on the type and frequency of updates you'd like to receive from your manager and/or team.
4. Allow enough time to ramp down so that you're fully handed off by the time you go.

Disconnecting from work while on leave

 When work takes up 8+ hours of our day, it can be hard to disconnect when preparing to go on PTO or a longer leave. At the same time, putting work aside is essential in order to fully benefit from time off, or be fully present for the life events, health issues, personal needs, or family exigencies that require your attention.

 Here are few tips for how to truly turn off and tune out while you’re away:

• Remove your work email and Slack from your phone and computer. This makes it harder to connect because you’ll have to reinstall the app or type in the password, and that extra step gives you time to pause and ask yourself whether you really want to log in after all.
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• Set up a system for escalated emergency updates so that you know, and your team knows, in what situations you want to be contacted. This allows you to step away knowing that your team will get in touch if needed.
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• Set up a Google Doc or Form where your manager and/or colleagues can share updates that you aren’t required to respond to, or even read until you return. If you’re curious, you can always take a look—without logging into Slack or email.
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• Use email filters to avoid returning to email overwhelm. Set up an autoresponder telling people that all mail will be archived and marked as read unless they send it again with “[YOUR NAME] README” in the subject line—in which case, it’ll be sent to a special README folder. When you return, you’ll have inbox 0 and only have to read the messages in the README folder.

Returning to work after leave

People returning from an extended leave may find themselves returning to a team or department that’s very different from the one they left. Things may have changed or evolved significantly, and there may be new teammates the returnee hasn’t met and isn’t aware of. It’s easy to start feeling lost or overwhelmed, or struggle to regain one’s footing. So how can you reintegrate when returning from leave? 

You can start by setting up social calls, sitting in on meetings you don’t normally attend, and watching recordings of key meetings you missed (block time in your calendar to do this in your first day or two back!). Ask your manager, teammates, and other close collaborators who you should meet and what you need to know. Keep in mind, however, that those questions might put other people on the spot. You might ask people to drop notes for you in your Google Doc or Google Form when they think of things while you’re away, and then you can review it all in one place when you return.

 Be aware that readjusting to work takes time, so allow yourself to ramp up slowly and don’t expect to hit the ground running on day one. If you’ve been away for a while, your brain will need time to readjust to the rhythms and demands of the job, and you may find yourself getting tired pretty quickly at first. How long it takes to reacclimate depends on how long you were away. For a couple of weeks, 2-3 days might be enough to get back up to speed. But if you were gone for a year, you may very well need 2-3 months, especially if you’re coming back to a different team or role, or a different set of responsibilities. It’s helpful to think about a re-onboarding phase, similar to onboarding for new hires. Managers and People teams should be there to support you in this process.

If your leave coincided with a major life event, such as marriage, childbirth, illness, or bereavement, that makes it especially important to ease back in gradually. You may be returning in very different circumstances from when you left—you may feel like a different person, or have a new perspective, or a new set of priorities. Your mental state, well-being, and energy levels may be impacted. All of this might affect how it feels to return and reintegrate into the workplace. Allow yourself time to think about how your new life and your work life fit together, and what you’re bringing to work that’s different from before.

Embracing change

The first step to set yourself up for success when taking time off is to recognize that things are likely to be different when you return. Embracing that change with an open mind will make it easier for you to set reasonable expectations and reacclimate sustainably. 

The important thing is to check in with yourself as you slowly reintegrate. Are there habits you learned while away that you want to carry forward? Have you had new insights or revelations about yourself or your work that have changed your relationship to work? Are you finding that you approach problems differently, struggle with things you didn’t before, or notice things about the business now that you’re seeing it with fresh eyes? These are excellent opportunities for learning and growth, and as you settle into the next phase of your working life, your team will also benefit from the wisdom and new perspectives you’ve brought back from your time away.

The Greek philosopher Heraclitus famously said that you can’t step into the same river twice. The river has changed. You have changed. It’s only natural to approach the rushing water with trepidation, but with the right planning and support, you can navigate the current with a greater degree of confidence.

About Oyster

Oyster is a global employment platform designed to enable visionary HR leaders to find, hire, pay, manage, develop, and take care of a thriving distributed workforce. Oyster lets growing companies give valued international team members the experience they deserve, without the usual headaches and expense.

Oyster enables hiring anywhere in the world—with reliable, compliant payroll, and great local benefits and perks.