• Carol Reeve

Building a Seaworthy Organization



I was sailing before I was born. Even nine months pregnant, my mother was crewing for my dad aboard a Pintail. Just weeks after my birth, my dad secured a strap-on infant bicycle seat to the back of the boat; I literally dangled over the water. Our summer vacations were spent cruising the Chesapeake Bay on chartered sailboats. In sail camp I earned the prestigious first place trophy for my age group.

Although I’m not a sailor now, principles of sailing have guided me throughout my life. Here are some that apply well to small businesses and nonprofits.

  1. You can’t sail if you’re looking down at the boat. Telltales are pieces of ribbon affixed to both sides of a sail, near the top. When a sail is trimmed perfectly, the telltales fly out straight, parallel to the horizon. If you spend your time looking down at the boat (working in the business instead of on the business), you’re probably not catching all the wind you could. Lesson: Chart your course, look up, and aim high.

  2. Sailing directly into the wind leads to chaos. When a boat points directly into the wind, all hell breaks loose. The boat comes to a screeching halt, rocking back and forth, with sails and lines clapping and slamming. The heavier the wind, the greater the chaos. If your vision is taking your organization directly into the wind, you may need to alter your course slightly and zig-zag your way there just to keep moving. Going against the flow in business takes fortitude and some degree of tolerance for chaos, but too much will paralyze your organization; rarely is the road to success a straight course. Lesson: Be prepared for a less direct path.

  3. Know when to batten down the hatches. Good captains watch the clouds, smell the air, and study the seas. If you sense a storm coming, make a plan. Ready your crew. Show clear and decisive leadership, and delegate specifically. If you lead well, your team can emerge stronger and more empowered after even the toughest storm. Lesson: Your team is counting on you. Stay calm, and lead with confidence.

  4. Don’t take fragile items on board. All it takes is one capsize to realize that expensive sunglasses have no place on a sailboat. Got ego? Leave it ashore, mate, because when the wind picks up, no one has time for it. Lesson: Don’t allow ego into your culture (that includes you).

  5. Don’t wait until you’re in deep water to find out a crew member can’t swim. A storm at sea is not the time to discover that one of your team members is lacking a critical quality. Don’t assume just because he can tie a good bowline knot that a candidate is worth his salt. Check references, run assessments, ask for sample work; heck, push him off the dock and see what happens. Lesson: Screen carefully for character, culture, chemistry and competency before you hire anyone.

  6. Trust your crew to do their jobs. If your team members are not performing well, give them the feedback and resources they need to improve. Set aside a day to get back to basics. Review all the positions on the boat so each member is reminded that what they do impacts the whole team, the direction of the vessel, and the speed of the journey. Lesson: You can’t do it all yourself, so make sure your team is well trained.

  7. You must start and finish the race with the same number of people. Although not part of America’s Cup standards, this rule is common among sailing clubs. A strong team cares for its own. Throwing a life ring and saying, “We’ll pick you up on the way back,” is not leadership. Have a “Man Overboard!” policy to ensure your team members know you care about them. If you see an employee struggling, call a “Mental Health Day,” schedule a retreat, or find another creative way to energize the entire team. You’ll find that you can sail much further distances with your team if you stop for an occasional swim. Lesson: Be proactive to keep your employees from burning out.

  8. If you can’t stop for a swim, pour a bucket over the head. Sure, #7 sounds great (“Let’s all stop in the middle of this giant project and go on vacation!”). But in reality, sometimes that’s just not possible. I remember many sweltering Knoxville, Tennessee summers in which I sat in a pool of sweat under a glaring sun, staring at sails that were perfectly still. Dad wouldn’t let us jump in during a race, but sometimes he would show mercy and drop down a bucket, scoop up some water, and dump it on our heads. And sometimes that was just enough to get us past the finish line where we could safely take a plunge. Lesson: Find creative ways to refresh each other.

  9. Sometimes you have to choose between jetsam and flotsam. When a vessel hits rough seas, and it’s apparent that it may not survive, the captain faces a critical choice: jetsam or flotsam. Jetsam is cargo that is tossed overboard to lighten a ship’s load so it can ride higher on the waves. Letting go of that cargo (or that product or that toxic client) can be painful, but making the conscious decision to jettison the jetsam can save the vessel. Flotsam? That’s the wreckage of the entire ship. Lesson: Let go when you need to.

  10. Keep your head down. A shift in wind direction can swing a boom and knock you out or, worse yet, knock you in. Pay attention to the market around you. Technology and trends can shift quickly. If you’re not prepared, you can become obsolete overnight. Lesson: Follow business news, at least peripherally, and stay nimble.

Moving along the water by harnessing the pure power of the wind is an exhilarating experience. It’s not one that comes easily, and it definitely has a steep cost of entry. But when you’re in the midst of it, there’s simply no other place to be.

Similarly, it’s hard to overstate the sense of reward and accomplishment you feel when you harness the power of people to move an organization or an idea forward. And when you really like the people in your boat, life is good. Really good.


  • Girl on the Roof Facebook
  • Girl on the Roof Twitter
  • Girl on the Roof YouTube
  • Girl on the Roof Instagram
  • Girl on the Roof LinkedIn

Winston-Salem, NC

call:  865.742.3409     email