Headed Out of the Office? Five Vacation Tips for Entrepreneurs

As an entrepreneur, taking a vacation poses many challenges and questions. Will your business manage with you out of the office for a few days? Will customers and clients remain pleased? Can the business operate as normal? How will the team handle emergencies? As a small business owner, I grapple with these very questions each time I vacation. Leaving a business and trusting that nothing will go awry requires a leap of faith. However, time away provides the opportunity to refresh and renew, which benefits every business owner and - in turn - their business. Here are my five tips for success when heading out of the office for a vacation:

TRUST SOMEONE: To ensure nothing falls through the cracks while you vacation out of office, appoint a trustworthy person to temporarily fill your shoes. Direct all other employees, clients and vendors to that surrogate. Ensure he or she has access to relevant accounts and decision-making authority where required. Of course, provide pre-planned availability for that right-hand man or woman in an emergency; if only one person has access to you while you play, this person’s it.

And, don’t forget that a token of appreciation for this person’s hard work will go a long way to keeping him or her engaged and responsive while you sip your piña colada on a warm beach!

MAKE A PLAN: Consider all factors and events that may come into play while out of office. Set up plans - and contingency plans - in advance.

For social media, if properly planned and executed, managing a campaign remotely can be very successful with minimum impact to your vacation. This can also be said of other programs; front-loading work prior to a vacation goes a long way towards maintaining sanity while away. For emails, blog posts, billing, newsletters and a multitude of other items, working ahead and scheduling for future execution with appropriate software allows most anything to run seamlessly while you frolic. If pre-vacation time permits, you may even consider setting up programs a week or so past your vacation to allow for a more civilized return to reality after vacation - if that is possible.

SET BOUNDARIES: While you likely must work on vacation, plan to turn off and tune out for a good portion of each day. Identify the expected work windows each day when you will be available and have access to your email or other modes of communication. Inform your point person of those times and set the expectation that, unless in an emergency, you won’t be checking in before or after that window each day.

COMMUNICATE WITH EVERYONE: Once you have a trusted appointee, a plan for how things will work and your windows of availability identified, set out of office expectations with clients, employees and vendors. With enough prior notice and clear communication of a solid plan, any reasonable person will happily respect the boundaries of your personal life.

PLAY IT SAFE: Finally, with all other plans in place, consider how to safeguard your business from fraud while you are away.

I recently heard a story of an entrepreneur who went on vacation and left an out of office notification on her email. A hacker from overseas saw the notification and seized the opportunity for foul play while the boss was away. The hacker cloned her email, determined her company’s CFO via LinkedIn and emailed the CFO requesting an immediate wire transfer of a few thousand dollars for a supposed equipment purchase. Because the email appeared legitimate and the large purchase aligned with the business, the CFO completed the wire transfer… and the company lost a few thousand dollars to the hacker. Yikes!

While I communicate with employees, clients and vendors when preparing for vacation, I don’t advise advertising it via email notifications or social media. Hackers love a vacationing business owner; play it safe and keep your vacay plans quiet.

How do you and your team handle vacations? Do you plan to work while on vacation? I’d love to hear your tips as so many people plan to step out of the office and embark on summer vacations.