Over the holidays I was lucky to go on a once in a lifetime trip to the Caribbean. My family and I took a ​Windstar cruise​. The ship was beautiful, the service stellar, and the food delectable. Surprisingly, the Windstar crew taught me four key things about pitching.

It’s Easy to Pitch When You Have a Great Product

The Windstar crew focuses on extraordinary service with a smile. You feel spoiled the moment you step on the ship. The cabin stewards leave flyers to sign up for another cruise and there is a cruise consultant on board. They offer a discount if you book a cruise while cruising. None of these approaches felt sleazy or salesy because I was having such a good time. And the crew members’ enthusiasm is genuine.

Use the Cruise Way: Make your story shine and it will be fun for you to pitch and fun to listen to.

Connect with Your Audience

Even though we were only on board a week, the crew from the the captain and general manager to the servers and stewards, learned our names and were always excited to see us. They made the passengers feel special.

Use the Cruise Way: Whether you are pitching in person, with a pitch deck, or on a sales page, how can you make your audience feel valued? What can you do to turn them into fans? Tell a gripping story that they connect with emotionally. It may be your idea, but the audience is your boss. Always over deliver.

Make Your Pitch Feel Like a Party

The Windstar people loved what they did and made pitching fun. They threw two parties where they pitched other cruises and asked for good reviews. One was a Tahitian cocktail party where they talked up their signature cruise to Tahiti. The other was the captain’s farewell dinner where the passengers got to applaud everyone that had been taking such great care of us. Both were lots of fun.

Use the Cruise Way: Make your pitch feel like a party! Be entertaining and fun. Think outside the box. Can you bring a snack that fits in with your project? Or ask to have your meeting outside? Be fun and memorable.

Take Every Opportunity to Pitch

And finally, always be pitching! Yes, they pitched us every day, but it was not overkill. Every pitch felt authentic. The climax was one of Windstar’s other ships sailing by us with her sails full on our last night. Talk about a movie moment!

Use the Cruise Way: ​Be ready to pitch anywhere, anytime.​ Don’t miss your movie moment.


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