When one of your main team members takes a vacation, it’s a good thing—they deserve the break. But let’s be honest, it can throw a wrench in your workflow if you’re not ready for it. The good news? With a little prep, your business doesn’t have to skip a beat.
1. Know It’s Coming, and Plan Like You Mean It
Don’t wait until the week before to figure things out. If someone’s planning a trip, get the dates early. That gives you time to sort out coverage, outsource to professional freight handling services for a short time, move deadlines around if needed, and make sure the rest of the team isn’t blindsided.
Using shared calendars and a decent project management tool makes this way easier.
2. Teach People More Than Just Their Job
This one’s big. If only one person knows how to run payroll, or update the website, or talk to a certain client, that’s a problem. Cross-training isn’t just for emergencies—it’s how you build a team that can handle anything. Plus, folks usually like the chance to grow their skills.
3. Talk It Out Before They Go
Don’t wait until they’re packing their bags. Sit down and walk through what’s on their plate. What’s urgent? What can wait? Who’s handling what?
Also, agree on whether they’re completely unplugging or lightly reachable in a pinch (and respect that boundary). It’s about clarity, not control.
4. Automate the Boring Stuff
If your team is stuck doing repetitive tasks while covering someone else’s workload, it’s going to get messy fast. Look for easy wins with automation—like email responses, appointment reminders, or reports.
Not everything needs to be done by hand. This buys you breathing room when you’re short-staffed.
5. Trust Your Team, But Check In Wisely
You don’t need to hover. If you’ve planned things out well, check-ins can be quick and to the point. A quick Monday morning update and midweek touch base usually does the trick.
Your team wants to do a good job. Let them.
6. Write Stuff Down—Seriously
This one gets overlooked constantly. If someone’s role involves a bunch of “only I know how to do this” stuff, get it documented. A Google Doc with step-by-step instructions goes a long way when someone else needs to jump in.
It’s not about micromanaging—it’s about not reinventing the wheel every time someone’s out.
Bottom line? Vacations are healthy, for your people and your business. The key is making sure the rest of the team is set up to carry the load while they’re gone. Plan ahead, spread the knowledge, and lean on tools that make life easier.
Everything keeps moving. Nobody burns out. And your employee comes back rested, not to a disaster. That’s a win for everyone.
