Vacation Optimization For Busy Executives

The mere thought of taking a vacation can be a workaholic’s worst nightmare. Contrary to its meaning, the word “vacation” often elicits far greater feelings of fear, anxiety, and powerlessness for many in today’s fast-paced and hypercompetitive business climate. Just because certain individuals decide to take time off does not mean businesses can necessarily afford to stop growing. There are still sales to make and clients to follow up with regardless of your presence as a decision maker.

Many companies adopt a culture in which executives or decision makers are always on the clock – particularly those companies either in their infancy or a period of significant growth. For those of us that fall into this category, opportunistic instinct often has us answering emails to ensure that each client is taken care of without regard for time and place.

If you fit this description, then you’re probably also faced with the inevitable ultimatum from your husband, wife, girlfriend, boyfriend, child, or family pet to put your phone or laptop away at some point during a vacation getaway. When faced with this inevitable moment, don’t panic. Following a few simple guidelines can help you bridge the gap between work and play , while still being attentive and responsive to the needs of your business.

Inform Your Clients And Colleagues

Planning your escape should always include a well-timed update for your priority clients and colleagues. Giving them a four to five day notice of your vacation is enough time for both parties to tie up any loose ends. For extra peace of mind, send one additional reminder the day before you check out as a courtesy. Be sure always to provide your date of return and the contact info of your backup, and include the type of requests that are appropriate when reaching out to this person.

Work Smarter Ahead Of Time

Being proactive before your time away can make you and your vacation feel a lot more productive than it actually is. Instead of simply clearing your desk and going off the grid, try automating customer outreach during your vacation. Marketers, in particular, can hardly afford to arbitrarily designate a scheduled vacation as a time to simply ignore their customers. Triggered outreach services like GetResponse can help you target your most active users or shoppers with exclusive offers sent at the most favorable time, even in your absence. Or, use it to simply send a timely greeting to your customers who have milestones or birthdays during your absence.


Let your colleague know when you are redirecting emails to them. Keep in mind this will increase their workload, meaning that confirming they are prepared for the work is important. Someone might feel overwhelmed trying to fill your shoes, so make sure they feel confident categorizing all requests into one of three buckets:

  1. Simple request, easily handled by your backup
  2. Requires your attention, but can wait until you return
  3. Urgent matter that requires your immediate attention

Leave A Professional Out Of Office Reply

People don’t need to hear the exact details of what you are doing or where you are going. The last thing you want to do is come off as obnoxious or unprofessional. Choose your words carefully, and don’t over do it. Crazy fonts can be cute, but you never know who will be emailing you. Using your favorite Disney character and wacky font may relieve you of all credibility. If you feel like being spontaneous in your out of office reply, it’s ok, as long as you don’t go overboard.

E.g. “Leaving the country! Be back on 12/10/2016. For media inquiries, please contact….”

Keep it short and sweet, and avoid leaving detailed and complicated instructions in your message. Similar to the delegation tactic above, all requests can likely fall into one of three categories that rarely require an immediate response. Lastly, always double-check your message for typos. Nothing screams lack of professionalism than reproducing the same typo for two straight weeks.

Still Can’t Commit?

It’s ok. Don’t be ashamed of your inability to cut the cord and unwind. If the helpful tips above (and my passive aggressive encouragement) still don’t have you sold on the idea of powering down, try weaning yourself off the routine by assigning a dedicated time of day as your only window to respond to emails. Consider preparing a politely canned response assuring the recipient that you have received their message and will address the issue with 100 percent of your attention as soon as you return.

Bonus Tip

For the thrill seekers out there, try testing your resolve during your next vacation by selecting a destination known for its spotty phone reception and lack of available Wi-Fi.