The Guilt-Free Way to Take Time Off from Work

The benefits of paid leave—for employers and employees alike—are well-documented, but even if your employer has a generous leave policy, it's not always easy to take advantage of it.

Whether you're planning extended parental leave or a just a week-long vacation, you may feel guilty about leaving your coworkers to pick up the slack. You may stress about everything you'll have to catch up on when you come back. Or, for longer absences, you may worry that your career progression will stagnate while you're gone.

But with the right preparation, you can feel confident about how things will flow while you're out and be sure the transition back is smooth.

Preparing for Parental Leave or Extended Vacation

The good news about taking maternity leave, paternity leave, or vacation time is that you generally know ahead of time when you'll be out and for how long. You can prepare your supervisor, coworkers, and temporary replacement (if you'll have one) for your absence so that you don't come back to a load of unfinished projects or angry clients—or field panicked phone calls in the delivery room.

Here are eight things you should do before heading out that will benefit you, your coworkers, and your company at large. And keep in mind that, while these are intended to be used for extended leave, they can also come in handy for unexpected absences like sick days.

1. Create a shared calendar

Map out your big or ongoing projects to see which deliverables will be due while you're out. Then make a list of recurring tasks along with their frequency, like monthly client calls or weekly progress reports.

Using this information, create a new calendar in your calendar app, and then share it with everyone on your team. (Or, if you're comfortable, you can share your existing calendar, as long as it's not too cluttered.)

For example, you might create a calendar called "[Your Name] Leave Tasks." If you're using Google Calendar, anyone who's shared on the calendar will be able to view it, and then you can invite key people to specific events so they get a reminder. Alternatively, you can use the following Zap—our term for an automated workflow—to automatically post upcoming events to the appropriate Slack channel.

By creating a shared calendar and being sure notifications are set, you'll ensure that nothing slips through the cracks, whether it's a big project or a monthly recurring task.

2. Document your processes

If you work with specialized tools—whether it's for project management, customer relationship management, or anything in between—don't assume that everyone else will know how to use them. Product knowledge bases can be overwhelming for new users, particularly if they're just looking to take care of one quick task.

Provide over-the-shoulder training if you can, and use screen recording software to record walkthrough videos of your most commonly performed tasks. Of course, you don't need to record yourself sending an email—you can assume everyone can handle that. But, for example, you might record yourself accessing and updating your project management app. Record your screen as you log in to the app, create a new task, update an existing task, and so on. Anything you find yourself doing regularly should be recorded.

When possible, you'll also want to create templates for your processes.

• Create a template of talking points for recurring calls or meetings.

• Create document templates for emails, presentations, spreadsheets, and anything else you make on the regular.

• Create pre-saved reports in your analytics tools for any data that you think your coworkers will want easy access to.

If you use Google Docs, you can even set up a workflow to automatically fill in templates whenever your coworkers take actions in other apps—that way, they don't need to lift a finger to fill in the existing templates.

While you're documenting your digital life, a couple other things to remember:

• Make sure the information within your apps is organized. Give your tasks and files searchable, informative names; create folders to group related items; and remove (or at least move) anything that won't be relevant while you're away.

• Change your notification preferences in your apps. If you get an email every time someone assigns you an Asana task, for example, be sure that those emails get forwarded to someone else instead (you can use a Zapier workflow to automate that). You can't always trust that people will remember to assign tasks to whoever's covering for you, so you need to be sure you've covered your bases.

3. Transition clients and other contacts

If you work directly with anyone outside of your organization—whether that's freelancers, clients, vendors, or anyone else—you want to be sure your coworker (the one who's covering for you) and the external contact know each other.

For your contact, be sure to send them an email introducing them to whoever will be taking over communication for you. Include the dates you intend to be out of the office so they aren't surprised when they get your out-of-office auto-reply, and try to send these emails early enough that your contact has plenty of time to ask any clarifying questions before you leave.

For your coworker, leave notes about each contact (you can put the notes in your CRM if you use one, or create a spreadsheet to log the info). Include notes on when they might need to be in touch with this contact, their preferred mode of communication, and any other information that might be useful in navigating the external relationship.

We suggest asking to be cc:ed on all communication. That way, when you're back, you can get caught up on what you missed. Plus, you'll be able to search your messages for any relevant information down the road instead of having to ask the person who was covering for you.

4. Share account credentials and passwords

You don't want to hear from your coworkers while you're away. But you really don't want to hear from them for something as silly as, "What's your password for [insert app here]?"

The easiest solution is to use a password manager with shared credentials. Create shared accounts for your project management tool and any other important apps, and be sure your colleagues have the appropriate permissions in the app (e.g., user can both create and edit tasks). If everyone on the team signs up for the password manager, they'll be able to access your apps in just a few clicks without you having to write your passwords on a sticky note.

If you can't get everyone on board, invite specific individuals to create accounts for the relevant tools they'll need to access while you're out.

5. Distribute your workload and document ownership

No matter how much you've prepared, it won't matter if the people back in the office don't take ownership of everything you've teed up for them. First, you need to speak individually with everyone who will be covering for you.

Then, to help ensure accountability, create a public document sharing who owns what. We suggest creating a spreadsheet, and here's what you need to include:

• Column A lists the task or project. Give each task a brief but descriptive name (e.g., "Vendor communication") to make the list scannable.

• Column B lists the person responsible. Once you're done creating the spreadsheet, you can order it using this column so everyone can easily see what they're responsible for.

• Column C lists the contact info for the responsible person. Put the owner's email address or Slack handle here. Especially if you work for a larger organization, this'll be important.

• Column D links to relevant documentation. Link to any process documentation here, or link directly to the task in your project management tool if relevant. To avoid having lots of different links, you can include any other relevant links within the main documentation.

• Column E is for notes. Anything else relevant can go here, but try to keep it brief. Most of what people will need access to should be in the main documentation for that task or project.

Be sure to share this spreadsheet with everyone in your organization so that everyone can get in touch with the right people when the time comes.

6. Manage your inbox

To avoid days of clean-up when you come back to work, take a few minutes to manage your inbox before you go.

• Unsubscribe from newsletters (since they'll be irrelevant by the time you get back), or filter them into a specific folder so they don't bury other, more important messages.

• Consider creating filters for emails from important contacts; that way, it'll be easier to go back and review what you missed from them. Even though you'll have someone covering for you, you'll want to reach out and let them know that you've had a chance to review all the correspondence.

• Write an out-of-office message that summarizes how long you'll be out and who to ask for help in your absence. If you're using Gmail, we suggest customizing your out-of-office message depending on who's emailing. That way, if someone emails from inside your organization, you can link to the ownership document, so everyone knows who to contact while you're out. Or you can create special responses to different groups (clients, vendors, and so on).

If Slack is where you do most of your communicating, you can take similar action there, creating autoreplies to be sure the right people get the right messages.

7. Make a communication plan

Decide how connected you want to be during your absence. It will look different for everyone, so what's important is that your supervisor and coworkers know your plan. You want to let them know how responsive you plan to be—if at all—and what constitutes an emergency or reason to reach out. We suggest you write your plan down officially and share it with relevant people in your organization.

Here are a few examples, but remember that each person's communication plan will look different, depending on their role and personal preferences.

Totally disconnected communication plan

I trust that you'll all be able to take care of everything while I'm gone! If there are any issues, I'll be more than happy to address them when I'm back, but otherwise, don't plan to hear from me while I'm away. I won't be checking email or answering work phone calls, and I'll be deleting Slack from my phone. Looking forward to getting back on [date of return]!

Semi-connected communication plan

I trust that you'll all be able to take care of everything while I'm gone! If there are any emergencies, please have [name of person] contact me by text message and let me know exactly what's going on so I can address it as efficiently as possible. An example of an emergency would be [X client] asking to terminate their contract.

Otherwise, I will plan to check my email once a week and respond to anything labeled _Urgent in the subject line (please use sparingly!). I may not address issues in full, but I'll be sure to respond to those urgent messages so you know that I'm aware of what's going on. Looking forward to getting back on [date of return]!_

Very connected communication plan

I trust that you'll all be able to take care of everything while I'm gone! I'll be checking my email every other day, so I'll be in the loop. If there's anything specific you'd like me to address (as opposed to just reading about), please send me a separate email with the subject line "Please respond: [topic]."

If anything particularly urgent comes up, feel free to call me at [phone number]. If I don't pick up, leave me a message letting me know what's going on, and I'll call you back within 24 hours. Looking forward to getting back on [date of return]!

Once you've set boundaries, make sure to stick with them to avoid sending mixed messages to your coworkers. Even one rogue response can start a spiral of overcommunication.

8. Prepare to come back

Plan for your re-entry now—otherwise you'll have to use up your precious leave time thinking about it. This is another spot that'll be different for everyone, but here are a few things to consider:

• For expectant parents, ask about options for coming back part time to start, using a flextime arrangement, or working remotely for some amount of time.

• If you anticipate needing time to pump breast milk, make sure you know where you'll do so, and consider blocking time off on your calendar now (with the understanding that your pumping schedule may not be predictable).

• Ask if you can start midweek, so you only have a few days before you can rest again on the weekend.

• Block off time on your calendar as Busy for some amount of time when you get back. If you've been out for a week, give yourself the first four hours that you're back in the office. If you've been out for three months, block off at least a few days. Use this blocked-off time to get reoriented and caught up on what you missed. (You might even want to extend your out-of-office response so you have time to get your bearings before diving into new business).

All this preparation is key for a smooth time away from work. But just as important: your mindset. You don't need to apologize for taking time off. Instead, make your absence as easy as possible on your coworkers and be sure to thank them when you get back—and, of course, return the favor in the future.

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