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Working While On Vacation: 7 Tips for CEOs

Working While On Vacation: 7 Tips for CEOs

By Kimberly Zhang

While some CEOs are bound by location, others are able to lead their company from anywhere in the world. As romantic as that sounds, we all know the reality is far from answering a few emails on an iPad in an airport lounge or spending most of the working day poolside in a resort community. The thing is, your job requires too much responsibility for that.

On the other hand, traveling is a big part of the entrepreneurial journey. Any hard-working executive will need to take enough vacations per year to reduce the stress and anxiety that comes with so much responsibility. Yet how does one do this without coming back to an overloaded inbox, a stressed-out staff, and so much work that needs immediate attention that you’ll never want to go on another vacation again?

Maybe you just can’t go off the grid for a long period of time. But there are ways you can work without jeopardizing the entire trip–we’re here to give you a few tips on how to do that.

Focus on Your Priorities & Communicating with Your Staff

Listed priorities are even more important when you know you have an upcoming vacation or trip. That way, you as a CEO, can ensure you work on the most critical tasks before leaving–or at least you’ll have enough preparation done in case something comes up while you’re away. The last thing you want to do is waste time hunting down information to help you make a critical decision while your friends and family are begging you to put the phone down and join them. Put yourself in a position where you can be briefed by your staff, make a decision, and get back to your vacation.

Anything that isn’t urgent or essential should be delegated to trusted members of your senior staff. If someone serves as acting CEO in your absence, that person should be able to triage anything that arises and decide if it can be handled by someone less senior or if they need to contact you. Long-term projects with no immediate deadline can be scheduled on your calendar for after your return.

Pass The Baton

Delegating tasks before you go on vacation is crucial. Try to hand off some responsibilities to others. Hopefully, you work as a team and your team members will be happy to help when you need the assistance.

If you have the time, schedule individual meetings with these people to ensure that they know what you want done and how to do it. You should run them through the appropriate resources and make them feel comfortable with the tasks at hand. The last thing you want is a stressed-out employee who does not know what they’re doing. You want to reduce all incoming calls from people who are confused or frantic. Additionally, let your high-profile clients know who they need to contact in your absence with any questions or concerns. Don’t be afraid to put the responsibility in the hands of others!

Be Strategic About Your Downtime 

While on vacation, you’ll want to be strategic about your downtime. Are you an early riser? Use this to your advantage to get work done before anyone else is up. If you’re a CEO on a family vacation and you have children who take naps, use this time to make urgent phone calls or send work emails. Maybe you have a date night planned with your spouse and they take longer to get ready. You can use that time to your advantage.

No matter how many activities you have planned on your vacation, there are always moments of downtime. Make the most of this time, even if it’s just 30 minutes or an hour.

Plan Around Wi-Fi

You don’t want to assume that Wi-Fi will always be available for you when you need it. Depending on where you are in the world, it may be difficult to get access to strong Wi-Fi wherever you are. Sometimes, the location promises Wi-Fi, but the connection is not reliable and spotty.

Additionally, you’ll want to factor in travel times and try to plan the work you can do without Wi-Fi during that time. If you have a home base, like a hotel or Airbnb, this is the most reliable form of Wi-Fi you can count on. Otherwise, it could be a good idea to download a Wi-Fi finder so that you can plan where to get online without worrying about it last minute. By using a Wi-Fi finder, you can plan ahead of time and prioritize your tasks without stress.

Set An Out-Of-Office Message 

This is an excellent feature of some email providers like Gmail or Outlook. They actually allow you to craft an out-of-office message while you are on vacation. You may already be aware of this, as it’s an automated message that goes out to anyone that attempts to email you or schedule a meeting with you. However, we are here to remind you to set it up, in case you forgot!

Ensure that it includes some key information such as

  • Exact times and dates you’ll be gone
  • When you will return
  • Names and contact info of the people who are assisting you in your absence

Don’t Make Empty Promises 

I know that as a CEO, you’re probably used to taking on a lot of work and getting it done efficiently. However, make sure you aren’t making any false promises that you can’t fulfill. Be sure you don’t overextend yourself the week or two that you are on vacation. Plan just enough for you to handle and try not to overwhelm yourself with both vacation activities and work!

Additionally, make sure that your vacation doesn’t turn into more of a burden. For example, don’t try to plan a Europe trip in four days. Instead of feeling relaxed, you will feel more stressed out.

Unplug And Unwind 

CEOs, this time is about you! Remember, it is your chance to relax and enjoy some time work-free. Make sure your vitamin D levels are replenished and spend some time outdoors. After all, working typically requires a lot of time inside an office or indoors. Vacation is an excellent time to re-calibrate and give yourself a mental health break. If you take this time off, you will return to work more motivated and rejuvenated than before you left! Sleep in and have some fun in the sun.

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