How to Prepare For (and encourage) Your Team’s Vacation

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The constant hustle of building a business can make a vacation tough to plan for any business owner. It can also be difficult to prepare for any team vacations when you rely on each and every member of your team on a daily basis.

Despite that, encouraging your team to take time off is essential to their morale and happiness overall.

This is also true for you as the owner and CEO!

As tempting as it is to hope your team is always available, you’ll foster a better environment for yourself and your team by planning ahead and managing time off with grace.

Start With a Calendar

When you have several people working in the business, balancing time off all starts by knowing who is going to be gone at any certain time. Consider using a shared calendar that everyone can add to and view when making plans.

You’ll need a different process for employees and contractors when it comes to time off. With employees, time off is generally more of a request that requires approval situation so you’ll have more oversight on the time off. With contractors, you can’t approve (or disprove) time off in any real sense since contractors by definition control their own schedules.

That said, when you work with contractors on an ongoing basis, there should be some consideration given to the business needs when determining deadlines impacted by time off. If you have a big launch that happens every year at the same time, a contractor isn’t serving you well if they’re suddenly unavailable without warning and they can’t meet your deadlines.

This applies primarily to scheduled time off rather than an emergency or other unforeseen issues impacting availability. One of my business mentors shared her frustration about a contractor who decided to take three weeks off right before a huge launch that happened every year in the same month. Even more frustrating, the contractor seemed completely unaware of why deadlines were moved forward to ensure her parts were completed before she left.

The Prep Ahead Items

Once the time off is planned, the real preparation begins.

Start by going through the regular tasks your team member is responsible for to identify anything that can be prepped in advance. These things may need to go live on a certain day but can be pre-scheduled and automated. Things like blog posts, newsletters, some social media postings, and even some personal inbox emails can be created in advance and pre-scheduled.

Be realistic about what your team can prepare with their normal workload and focus on things you can’t (or simply don’t want to) execute on your own. Even if you’re left with a few things here and there, this will take a lot off your plate while they’re gone.

What About the Real-Time Tasks?

There are likely things that need to happen in real time, especially if your team member handles day-to-day admin. Again, start with capturing the daily and weekly tasks your team member handles. If you already have checklists in place, ask them to do a quick review to make sure nothing needs updating or deleting before they go.

You’ll likely find that tasks like inbox management, customer requests, social media management, community management, blog posts comments, and help desk requests fall into the real-time category.

Once you know what needs to be covered, consider who else on your team has the necessary skills to help out. Your instinct may be to dive in on our own and cover it all but this isn’t likely the best use of your time.

If needed, once you’ve determined who’ll cover these tasks, plan on some cross-training on the established processes. This will help not only with the current needs but also for future coverage needs as well. While it may seem silly to take the time to do this training just to cover a few days off, it’ll pay off in the long run.

Let The People Know

Once you have the plan for keeping things running nicely while your team member is gone, be sure to let any clients or other team members know if it’ll impact them. For a short absence, a ton of notice is not likely needed but if you’re looking at a longer hiatus, be sure to provide notification as early as you can.

When you let clients know, be sure to include details on how you plan to plan to take care of them. For team members, you’ll want to set expectations on how it may impact their workflow.

Proactively assuring clients they’re still in good hands goes a long way towards keeping things running smoothly.

Lastly, make sure an out of office message is set up on that team member’s internal email.  Include instructions on who to contact if the request is urgent as well as an estimated return date of the message if it’s not.

Make Time Off a Priority

There you have some simple steps to manage a team member’s time off. These steps will help you and everyone else on your team feel empowered and cover their tasks while they’re gone. This, in turn, will make it easier for the team to feel like it’s ok to take time off.

Just as important, it’ll also encourage you to take some time off yourself! The importance of time off can’t be emphasized enough. Downtime is an essential ingredient in preventing burnout and overwhelm.

Keeping things running while dealing with team vacation is all about planning. Here are five tips to get you organized.

What kind of entrepreneur are you?


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