Small Biz Advice: Taking Vacations


holly-photo-280x290Dear Holly,

I run a small production company here in Brooklyn with about 10 employees.  It is now five years since I started the business.  I think I have a really strong team, but I have a really hard time taking time off.  I don’t know if it’s because I’m a micromanager or if it’s because I fear my staff will be upset if I’m not there, but I rarely take a vacation.  It’s really starting to get to me, and I’d like some advice on how I can set myself up to take a vacation successfully and ensure that nothing slips through the cracks and everyone feels good about it.



Dear Vacation,

This is a great question because it’s often a scenario that business owners fail to execute in a productive way.  You want to build a business that runs itself, but you must also recognize that your staff looks to you, the owner, for inspiration and vision.  Someone always needs to be setting the tone and the direction for the business.

Taking vacation is actually very good for business.  It allows you time to clear your mind and gain perspective on how things are going.  It’s a myth that we need to be tied to our businesses all the time.  It’s actually quite counterproductive for business growth.    Here’s what you can do ensure a stress free vacation from your business.

First, get clear on your role within the business.  As the owner, you should be focused on areas of the business that don’t require daily maintenance.   After five years in business, your time should be spent working on the development of the big picture and not the day to day operating tasks.   Re-evaluate what you’re doing now and what you might need to delegate in order to create this type of position for yourself.  Like I mentioned before a large part of your role is to provide the vision for the company and the keep your staff motivated.  Make those pieces a priority within your role.

Once you’ve accomplished this, focus on your team.  Have you made their roles clear enough that they know what they are responsible for on a day-to-day basis?  Have you trained them properly so that you don’t need to constantly be looking over their shoulders and they don’t need to constantly be checking in with you?  Both of these are very important if you want to spend time away from your business and not have things fall through the crack.  Make sure all of your team is clear on their roles within the business and that they are well trained to do their jobs.

Finally, create a vacation action plan.  Give your team at least two weeks of lead time before you take your vacation.  People always do better when you give them warning rather than just jumping ship.  It will allow them to ask any questions about how to handle things while you’re away.  For instance, do they know how to handle emergencies while you’re gone?  How would you define an emergency and when should they check in with you about them versus when they should handle the emergencies themselves?  For example, call me if there is a fire, but if the printer breaks down, call the maintenance man yourself. If you want them to handle emergencies, have you provided them with the resources they need such as appropriate phone numbers or methods of payment?  Give them direction about when to contact you and when to hold their thoughts until you return.  Do you prefer they send you a daily summary of business or would you rather they didn’t contact you at all?  It’s really for you to decide what level of interaction you require; there’s not a one-size-fits all vacation plan.  Make sure you are clear with them and that you have provided them with the resources they need to keep the business running while you’re away.

These three simple steps will set you up to take a vacation without having to worry whether or not things are ok back at the business.  Do your homework and you can leave confident that everyone will benefit from your time away.

Good luck!


Holly Howard runs Ask Holly How, a small business consulting company based out of Williamsburg, Brooklyn that works with a wide variety of businesses from restaurants to retail to art studios and pretty much everything in between. Her clients report increased income and profit, decreased expenses and a significantly better quality of life. Holly heads up the Small Business Book Club at McNally Jackson Books.

Want valuable insight into how to grow your business?  Holly hosts free 30 minute strategy sessions at The Yard in Williamsburg.  Email her to set up a time or to ask a question for the next Ask Holly How.

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