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Twelve Tips for Managing your Business during a Vacation

Twelve Tips for Managing your Business during a Vacation

By: John Rossheim, Monster Senior Contributing Writer

Managers and vacations don’t always mix. So how can you possibly pull yourself away from your young business for two weeks to take a vacation that you’ve needed for five years? Just think of all the things that could go wrong: all of the operational flubs that could go unanswered, all of the poor decisions that might be taken, all the accounts that could be lost. You’ve climbed every mountain to become a successful small business owner, so how can you possibly leave business in the hands of your handful of employees while you go mountain-climbing?

Because without the work life balance and perspective that a holiday provides, you won’t remain an effective executive.

“I was that guy checking email at the beach – not a good thing,” says Scott Miller, a serial entrepreneur who in 2010 launched The Bee, a web-based financial application. “I just decided to take the risk.” During a month-long family vacation in New Zealand while he was running a previous venture,

Miller had absolutely no communication with his staff or clients. “I gave my staff our itinerary, but I wasn’t going to make it easy for them to reach me. They handled issues on their own and made some great decisions.”

Don’t feel ready to take the plunge and revamp your management style? For your pre-vacation reading, scan these dozen top tips from seven entrepreneurs who know how to take a small business vacation.

Get clients familiar with your proxies. Don’t let your email auto-responder be the one to tell your customers who to contact while you’re on a two-week pleasure trip. “In the client contract we make it clear that my non-equity partner and contractors might get involved; transparency is important,” says Erin Powers, owner of Powers Mediaworks, which represents law firms.

Network it. Network with other small firms in your industry and exchange resources when principals go on vacation. “It does require a high degree of trust to work with people who are occasionally your competitors,” says Powers.

Who will do your duties? Enumerate and delegate your daily activities, one by one. Rob Jager, principal of Hedgehog consulting, advises: “Look for tasks that only you do. Ask yourself, is it critical that I do these tasks? Identify who on the team can perform them.”

Maximize opportunities for staff. Make a virtue of your need to depend on your staff while you’re away by asking your employees to do more. “It was great to see people step up and take more responsibility,” says Miller. “Looking in the mirror, it was obvious that I had been holding that back.”

What would Socrates do? Starting now, get in the habit of asking your staff lots of questions in the course of business. “Every time a problem or question comes up, a business owner should ask, ‘What would you do if you couldn’t get hold of me?’ ” says Jager.

Practice, practice, practice. “Practice being hands-off for longer and longer stretches -- even when you’re in the office -- to allow employees to get comfortable being in charge,” says Kate Koziol, president of K Squared Communications.

Prepare for the worst case. What’s the worst that could happen? Take this not as a rhetorical question but as a challenge requiring a detailed, documented response. “Put contingent action plans into place for what staff should do if something goes wrong,” says David Gammel, principal at High Context Consulting.

Meetings in brief. “While I’m away I don’t do all the Monday meetings, but I do have the COO brief me on them,” says Tracey Frost, owner of Citibabes, which operates membership centers that combine child care with adult fitness and related facilities.

Your admin keeps the trains running. “Behind every great entrepreneur is an amazing assistant who solves problems and handles things,” says Yao-Hui Huang, CEO of Gigapixel Creative. “Your assistant can take messages, call you in a block of time, get the answers and get back to people.”

Access when you’re remote. If you can’t entirely avoid doing business while on holiday, consider making advance arrangements for virtual meetings and remote access to documents via secure download.

Smartphone as security blanket. If no news is bad news to you, do bring your smartphone but set limits on its use. “In some ways the BlackBerry gives you more freedom when you go away; I’d be nervous if I were out of contact,” says Frost.

Do a post-mortem. Debrief your team and critique yourself so that your next vacation is even more successful. Miller says if his preparations for vacation fell short in one area, it was business development. “When I returned, the sales pipeline wasn’t as full as usual. I could have done a better job by loading the pipeline with more pre-sales activities.”

Your small business vacation away from your business gives you the chance to learn some big lessons. Here’s Gammel’s teaching for entrepreneurs who are beyond the earliest stages of operation: “Owners should be working primarily on their business rather than in it.”

Of course, it’s difficult to imagine your bootstrapped enterprise carrying on while the owner is (you) is taking a vacation. Says Powers: “When you have your own business, it’s hard to let go. But it becomes more comfortable over time.” Miller also urges fellow entrepreneurs to get over it. “I thought it was going to be a huge deal, but it turned out not to be.”

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