How to Take a Vacation Without Abandoning Your Business

How to Take a Vacation Without Abandoning Your Business
Image credit: Illustration © Otto Steininger
Magazine Contributor
5 min read

This story appears in the April 2014 issue of . Subscribe »

Twenty years after starting 1-800-Got-Junk?, CEO Brian Scudamore took a sabbatical. Confident that his crackerjack COO, who had been on the job for 10 months, would keep things thriving while he was away, Scudamore headed off to cooking school in Italy. "I was very grateful to her that I was able to get away for five weeks," he says.

But it didn't take long after his return for Scudamore to sense that all was not well. To his horror, he realized that the COO had overspent company funds to near bankruptcy, had been trying to turn his team against him and was scheming to oust him.

Which brings us to the first rule of vacation planning: Make sure you have a team you can trust. Leaving one's business to others, even for just a few days, can fill an entrepreneur with anxiety.

"In the early years, I felt the weight of the world on my shoulders and believed that no one could keep the company going during my absence," says Todd Greene, CEO of HeadBlade, a Culver City, Calif.-based shaving-product company. "As a result, I hardly ever went away, and when I did it was not enjoyable."

Tips on long-distance management

Be stealthy. Edward Gilhuly, president of Left Communication, has learned that letting staff and clients know he's going away can provoke unnecessary anxiety and suddenly push back-burner projects to the fore. "I've found it's sometimes better to slip away with stealth but stay connected," he says. "Not long ago I spent a week at surf camp in Costa Rica. No work-related contacts ever knew, as I stayed in touch like normal with e-mail and phone. Maybe even more than usual."

Keep an eye on things. Todd Greene, CEO of HeadBlade, remains connected even when out of the office, relying on smartphone apps to watch over his site and his employees. "I can check the site performance with Google Analytics," he says. "I can log into the site to fix any problem or update. I can access financials, credit cards and bank info. I get e-mails, texts, faxes. I can view my desktop. Security cameras remotely allow 24/7 surveillance."

Keep talking. Chocolate Lab Apps' Elaine Henley has "fallen in love with Voxer. It's a walkie-talkie-style app that works so well when communicating with your team."

Pre-plan communication. Dhana Cohen, co-founder of the Women Inventorz Network, suggests that before a trip, you schedule e-mails to go out to any lists you maintain, "keeping you present and appearing to be working even if you take an afternoon on a beach." --S.D.

Business trips or vacations can be much less terrifying if one plans ahead. Now, Greene says, "before I leave on a trip, we have an officewide meeting and review everyone's objectives while I'm away. We establish the chain of command. At all times there has to be someone in charge who is accountable. I also sign a specific number of checks that go into the safe in case emergency purchases are approved and cannot be put on a credit card. One person is authorized to use the credit card, with a set limit."

Though a few business owners choose to cut off all contact with work when they're away, most stay in touch but allow their teams more autonomy than usual. "I use trackers in Google Drive that I ask my team to update daily," says Elaine Heney, CEO of Tipperary, Ireland-based Chocolate Lab Apps. "I can log on to these any time and see a detailed status of all my apps. I also like to get two weekly e-mail status reports from my manager, with the status of each app and a list of issues at the end. Both of these mean I only need to contact my manager if an issue arises."

Sabina Gault, CEO of Konnect PR in Los Angeles, is accessible to her staff at all times. "PR is an unpredictable industry," she says. "No matter how prepared you are, handling crisis communication is no fun." When on vacation, Gault does step back a bit. "I don't check on anything small," she says. "My team knows to handle everything." Her team also knows they can call when they need her input, such as when dealing with an unhappy client. "They might call and say, 'Here's what we think. Here's what we would say. Are you comfortable with this?'"

It took some time, but even Scudamore is back to being comfortable when he's away from 1-800-Got-Junk?. In fact, he still prefers to go dark while on vacation, going so far as to have his assistant change his e-mail password so he can't check in.

After returning from his Italian sabbatical, he fired the disloyal COO and several other people and pulled his company out of its tailspin. Now he maintains his position as the "vision guy" and has a loyal COO. "A CEO has to have a second in command that they trust with their life," he points out. "Someone that you can turn over your keys to."

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