How To Take A Vacation When You’re The Boss

Posted on January 16, 2018

With a little planning, it’s easier than you may think.

tropical beach

For the owner or manager of a contracting company, it can be hard to take a day off, let alone a two-week trip to Florida with the family. Not only can it make you feel guilty, the uncertainty of leaving the company you built can be overwhelming. For those leaders who oversee a host of critical jobs like billing, payroll and scheduling in addition to their day-to-day duties on the job site, a vacation can seem like an impossible mission. In fact, surveys show that almost half of all small-business owners take off only holidays, skipping vacations entirely.

man fishing off boat

On the other hand, most experts agree that it is necessary for any busy person to periodically take time away from his or her tasks. Humans can easily “burn out” if they don’t have downtime to recharge their mental batteries, and from a business perspective, a week or two away can give leadership a new view of challenges and fresh ideas for growth.

How then can the owner of a four-person electrical contracting business or the foreman of a three-person plumbing crew take time off without putting the business – or its customers – in jeopardy? Here are some proven tips for planning your escape:

Delegate Your Jobs
This is almost always the first step. If you believe that nothing will get done when you are on vacation, it’s probably because you are doing everything at your business. While that may be a badge of honor for some managers, it gets old very quickly. Find people on your team who you trust and start giving them responsibilities. By sharing the load, you make it much easier to get away.

Appoint A Substitute
Now that you’ve delegated some of your work, choose a reliable individual to assume leadership while you are out. Not only should this be somebody you trust, it should be a worker who looks forward to a challenge. You don’t want them dreading your vacations, after all. Ideally, this would be someone from within the organization, but if your company is too small for this to make sense, it might also be possible to “swap” vacation coverage with another contractor in your market with whom you have a good relationship. After all, they are probably dealing with the same vacation aversion that you are.

Take an hour or two a week in the months before your vacation, and let your team know that you will be “off the grid.” Maybe even take an entire day away from your job. See how your substitute and your team respond, and make any changes that are necessary to improve the experience for everybody involved.

Communicate Expectations
For example, define what an “emergency” is. Should your team call you if a tech doesn’t show up for work? See the first tip for guidance here. By empowering your people – especially the person you leave in charge – this can be much less of a challenge. If you do a good job of choosing your backup, he or she will make most of the same choices that you would have. That means they will only need to contact you in the event of a disaster. Also, make sure that everyone knows how to get a hold of you, when you will be available and what they should do if you are unavailable. This will make everybody more comfortable with your time away, and that means your time away will go more smoothly.

Schedule Times To Check In
If you absolutely cannot be “offline” the whole time you are on vacation, set a time to communicate with your substitute. If you speak every day at 7:30 a.m. before things get hectic, you can relax for the rest of the day knowing that your team has had a chance to approach you with anything significant. With that being said, once you are done checking in for the day, stop checking email and text messages and enjoy yourself.

Debrief When You Return
Finally, check in when you get back and give everyone a chance to let you know how things went. You may very well discover that things went better than you thought they would. In fact, you might actually be a little disappointed to learn that they didn’t really miss you at all. Remember, that’s a good thing! In fact, it is probably one of the most beneficial long-term effects of a boss taking time off: learning that all of the systems you’ve put in place work as intended (or, perhaps, providing you the opportunity to fix those that don’t).

The ROI of R&R
It’s time to take a break! Think ahead, and you’ll be able to relax and enjoy a vacation the right way. Best of all, by planning and empowering your people, you may find that not only do you feel better when you return, your business is healthier as well.

Planning Your Escape
Budget Travel ranked the top 10 most popular cities that Americans visit abroad:

  1. Cancun, Mexico
  2.  London, England
  3. San Juan, Puerto Rico
  4. Paris, France
  5. Toronto, Canada
  6. Rome, Italy
  7. Montego Bay, Jamaica
  8. Barcelona, Spain
  9. Punta Cana, Dominican Republic
  10. Nassau, Bahamas