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A CEO’s Guide To Taking Summer Vacation

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Bosses need breaks, too. Here's how to set your team up for success so you can step away and recharge, guilt-free.

Summer travel season is back in full swing this year, with one in four Americans planning to take at least one vacation thanks to a rebounding economy, easing Covid-19 restrictions and a growing number of fully vaccinated U.S. adults.

Workers everywhere are likely eager to unplug and enjoy a change of scenery after a year of lockdowns and work-from-home stress, but it can be more difficult for business leaders to simply step away. In fact, a Harvard study of CEOs found that those that did manage to take a break worked during 70 percent of their vacation days, leaving little room to rest, recharge and reconnect with family.

Thus if you’re thinking of skipping out on a vacation this summer, it is worth planning thoughtfully so you can make the most of the time away. Taking a vacation not only boosts creativity and productivity, it lowers stress and promotes better mental health, improves sleep and brain function and has even been found to contribute to an increased life expectancy. And for parents, a family summer vacation is the ideal opportunity to make lasting memories and connect with your kids in a meaningful way.

So, how can you step away from your business without the guilt, worry and stress that comes along with taking a vacation? How can you be sure things won’t completely fall apart without you at the helm? With the right planning and forethought, it is possible to enjoy a vacation while your business takes care of itself.

Here are three rules for preparing your business to succeed while you’re on vacation.

Rule 1: Begin with the end in mind

The initial step is creating a cohesive vision for what your vacation will look like and how your business or team will operate while you’re away with this in mind. First, decide how you want your time off to actually look and feel so you can set the tone from there. Things to consider include:

• Availability – Do you prefer to be completely off the grid, will you check in with your team regularly, or are you planning a fully connected working vacation? Will your trusty smartphone be at your side as usual, or tucked away in a drawer somewhere?

• Mindshare – Would you prefer to compartmentalize thoughts of business while on break, or allow them to take up their usual space in your brain?

• Communication – If you’re making yourself available, do you want everyone on your team to have access to you, or just a chosen few? How quickly do you plan on returning messages?

By clearly outlining your preferences, you’ll be better positioned to decide how your organization should function in your absence, especially if you’ll be largely unavailable. Determine the aspects of the business you’re directly involved in that require hands-on leadership and begin thinking through how you’ll address each one to get a secure strategy in place. It’s important to take the time to clarify this for yourself upfront before you share your plans with your team.

Rule 2: Prepare people and processes to ensure success (and do it early)

Once you’ve determined what an ideal break would look like to you, move backward to put the systems in place that will make it happen. Start preparing as early as possible to get everything and everyone up to speed so the business runs smoothly in your absence.

You’ll need to think about and clearly communicate plans around:

• Company leadership – Who will be responsible for making decisions while you’re away? Are there certain projects that will need leadership, or clients who will need a go-to point person? If so, determine who you trust to step in (or who can you train to take the lead) and how they should update you if necessary while you’re on vacation.

• Clients – In addition, you’ll need to prepare clients, vendors and any other vital contacts outside the company for what to expect during your break. Let them know who will be their new, temporary point of contact for any issues or concerns, and assure them your team won’t miss a beat without you.

• Communication – Set clear expectations internally around how, when and how often you can be contacted during your vacation, including who will have access to you and for what reasons. If you will be mostly unavailable through traditional means, consider putting a plan in place so you can be contacted in emergencies, or perhaps utilize options like Slack to send and receive messages versus email or phone calls that might rack up international charges.

Rule 3: Stay flexible

You’ve planned. You’ve put the people and processes in place to support your time off. And…now your VP of sales just put in her two-week notice. You might be able to shift her responsibilities onto someone else’s plate until your return, but you also might need to push back your vacation entirely until you have a new hire solidly in place.

If an unexpected event occurs leading up to your time off, as a business leader, it’s vital to stay honest with yourself, reevaluate your plans and adapt as necessary. Even the mental health benefits of a vacation don’t outweigh the risks of stepping away during a crisis. Take a cold, hard look at the situation and evaluate whether it requires a change of strategy, or even a change of your travel plans entirely, to keep things operating successfully.

Ultimately, as a CEO or business owner who has built and run a successful organization, you know how to position it to thrive in your absence. Approach your summer vacation just as you would any other strategic initiative. With thorough planning, goal setting and preparation, you can step away for a worry-free break and return ready to tackle your leadership position with new energy.


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