Catboats and Coconuts: Using Risk to Chart a Course to Inspired Selling

Sales is an art, and art means taking risks.

Early in my career, my mentor and late chairman of the company, took me sailing in his catboat on East Hampton’s Georgica Pond. There was a race going on, as there was every summer weekend, and Donald, a shrewd and seasoned captain, insisted on making inexperienced me his first mate.

The horn sounded, and some of the other boats quickly got out in front of us.  Donald gave chase, then suddenly peeled off and tacked to a calm corner of the pond. Before I could ask what he was doing, he explained there was a breeze that sometimes blew from this particular stretch of shore, and that if we caught it just right, it could carry us to victory. We waited, and the breeze never came. We lost the race, but I remembered the lesson.

Recently, I’ve taken on new responsibilities at work, which include upselling subscribers from basic to premium database products. The forum for these efforts is a half-hour training session on the basic, a guided tour through its content, features, and functions intended to answer questions while showing ease and speed of use, improvement of workflow, and the mechanics of finding, storing, sharing, and extracting the desired data. Bored yet? Yeah, me too.

As I was falling asleep, thinking of beaches and palm trees, a coconut fell on my head. I had the idea of adding a theme to these sessions, injecting some humor, and creating a narrative that included a number of natural jumping-off points to discuss features and benefits only available in the premium products.

The theme: Gilligan’s Island. The opener: I’m taking my prospects on a 30-minute instead of  three-hour tour. After all, how much time do you need to learn the basic product?

The nitty gritty: Here are some ways you can use the product to get your work done faster and get home earlier, so you’re not stranded at your desk for hours.

The lead-in to the value of upgrading to the premium product: The crew of the S.S. Minnow had to get inventive and make do with what was available. Can openers, juice presses, blenders, and other time-savers would have made their lives easier, but they were only available on the mainland, unobtainable no matter how much money Thurston Howell III threw at the problem, whereas features such as timely alerts, creating and saving specialized searches, and extracting lists could be had in the premium product for only a few dollars more.

I admit, it wasn’t what the trainees – a group of librarians, advocacy professionals, communications directors, and admins were expecting. They signed up to be trained, not entertained. I took a risk, and I could have smashed the boat into the rocks or ended up becalmed in the dead air of flat jokes. But that’s not what happened. The theme went over swimmingly, and the audience went overboard with laughter and appreciation. And requests for trials of the premium product started flowing.

So how can you translate this into your own success and bring themes into your sales process?

  1. Choose a theme with which you know your audience will be familiar. You are aiming for comfort, not shock and awe, and universals appeal for a reason.
  2. Choose a theme that is appropriate to the event in which you’re engaging. I selected a tour to complement my guided tour of the database.
  3. Let your audience participate and get in the spirit of things. Their comments and jokes are likely to be funnier than yours.
  4. Don’t overdo it. The purpose of themed selling is not to drive the theme into the ground or explore every last parallel. Your goal is to lead your prospects to the place you want them to end up, in a light-hearted mood that is conducive to exchanging cash for value.
  5. Be prepared to change course if your efforts fall flat. Proceed confidently, and don’t give up too easily, but be aware that sometimes, this approach doesn’t work, and you end up by stuck the shore of the pond. As soon as you discern that the breeze isn’t coming, switch to plan B. Developing plan B – and C, and D if necessary – will be the topic of another article.

Risk is risky, but being afraid or unwilling to take risks is often riskier. You may have only one chance to engage your prospects before you lose them and they float off into the distance of half-listening.

Donald only had time for one sailing lesson with me, and he took a risk to teach me what he knew about the art of sales. His lesson has served me well.


Leave A Reply (6 comments So Far)

  • Excellent points. That’s a good tip about using a theme and making sure its one that the audience will be familiar with. I’m especially encouraged that the humor was appreciated, since I’m known to find humor in things that normal people do not find laughable.

    • Gina, I’m glad you liked the article, and thank you for taking the time to comment. The familiar theme sets the audience at ease. There’s always a risk to using humor in sales, in that it can fall flat, but when it works, it is an extremely powerful tool. Keep doing it, where appropriate, and you’ll see the results!

  • Anonymous

    The Gilligan’s Island tune is a catchy one! I’m on board (pun intended) with your illustrations. It is definitely more engaging and thoughtful than a boring sales letter.

    • Thanks, Ashley, for being on board and not voting me off the island!

  • What a great example of a Go For It! mentality and creating an experience for your prospective clients.

    In addition to your specific tips for a more creative and engaging sales process, a big kudos for sharing your bigger “embrace risks” lesson. This lesson also has served me well in life and business.

    Looking forward to learning more from you about putting a contingency plan in place.

  • Love the idea of creating a theme people can relate to and build on. This engages the audience at whole new level. Wonderful article!