Taking real time off—actual vacation, not just “working from a beach with Wi-Fi”—shouldn’t feel like running away and leaving your teammates in the lurch. But let’s be honest: handing over your projects, letting go of your inbox babysitting, and resisting the urge to check Slack every hour? That’s tough. If you’ve ever come back from vacation to frantic emails, confusion, or a to-do list that doubled in your absence, you know prepping your coworkers is the difference between a relaxing trip and needing an ayahuasca retreat just to recover.
Here’s how to prep like a pro so you and your team can both breathe a little easier when you hit “out of office” (and so your boss welcomes you back with a smile, not a sigh).
Give the Heads-Up Early (And Remind Them Again)
Don’t drop the “oh by the way, I’m gone all next week!” bomb the day before you leave. Let your coworkers, clients, and boss know as soon as your vacation is booked—even if it feels ridiculously early. Then, about a week out, nudge everyone again with a quick, friendly reminder. This gives people a chance to bring up anything critical BEFORE you’ve got one foot out the door.
Break Down Your Tasks, Don’t Just Say “Handle It”
Take a little time to list out what you really do—ongoing projects, daily must-dos, and those random “can you just…?” requests that seem to pop up. For each, decide whether it needs to be paused, covered, or delegated while you’re away. If someone is stepping into your shoes, spell it out with more detail than you think is needed. Shoot for “anyone could follow this” simple, especially if you’re asking someone from a different department to pinch-hit.
Delegate to the Right People (And Avoid the ‘Hot Potato’ Game)
No one loves getting a mystery task with no clue what’s going on. Be clear about who covers what, and don’t pile everything on just one person. If possible, match tasks to strengths—leave tech stuff with the tech guru, and daily reports with your spreadsheet superstar. Tag team members individually in emails or Slack—don’t just send a blanket message and assume someone will pick it up.
Leave a Cheat Sheet—and a “Break Glass” Contact
Put together a doc with passwords (use a password manager for security!), file locations, key deadlines, and “this always comes up” FAQs. Most importantly, flag a coworker or your boss as the go-to contact for emergencies. Make sure everyone knows how to reach you only if it’s absolutely “the-building-is-on-fire” urgent.
Schedule a Quick Walkthrough Meeting
Set aside ten minutes for a group huddle the day before you head out. Run through the biggest tasks, answer questions, and double check everyone feels good. This is where you fill in the details that never make it into an email, and it’s your chance to thank your teammates for having your back.
Set Up an Out-of-Office That’s Actually Helpful
Use your out-of-office message to point people in the right direction and clarify response times. Add backup contacts and any updates about when you’ll check in (or that you won’t be checking at all—which, by the way, is totally healthy).
Trust, Unplug, and Resist the Guilt
Prep well, trust your coworkers, and remind yourself that nobody comes back to the exact same routine. Enjoy your break. Your work—and your teammates—will be waiting, but a lot more smoothly than before.
