[Greatest Hits] Take the Road That Scares the Hell Out of You with Christine Trippi, CEO at The Wise Pineapple

Getting to Aha! with Darshan Mehta

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In this Greatest Hits episode of Getting to Aha!, Darshan Mehta revisits his discussion with Christine Trippi, CEO at The Wise Pineapple, where she travels all over the U.S. to inspire, consult, train, and present keynote speeches based on some of the biggest ideas from her best-selling book: Yes Is the Answer: How Positivity, Passion, and Pineapples Will Transform Your Leadership and Your Life. With more than thirty-four years of experience, Christine is an award-winning hospitality leader in the industry. She’s so dedicated to her work that she left her six-figure salary at the largest travel company in the world to launch The Wise Pineapple.
When she’s not being an inspirational force within the hospitality industry, she’s hosting her podcast, The Wise Pineapple - Juicy Tidbits, as well as exploring the world and saying yes to adventure, “terrifying her hubby”.
Key Takeaways
👉 Christine's first Aha! moment came when she realized she wanted to work at a hotel. That experience ignited her passion for hospitality, taught her the power of saying “yes,” and led her to meet her husband. She learned that when faced with a tough decision, to choose the option that “scares the hell out of you,” because that’s where the real growth happens.
👉 Accepting a job that doesn’t challenge or excite you will quickly drain your energy and creativity. Christine reflects on her brief time as a front desk receptionist, where she felt unchallenged and dissatisfied. She learned that a job that doesn’t push you will leave you merely surviving rather than thriving. So, how do you know it’s time for more? Christine says it’s when you start hitting the snooze button on your alarm clock.
👉 Saying “no” can be uncomfortable and anxiety-inducing because it’s often associated with negativity. The best way to navigate this is by first building a connection with your customers. Getting to know them helps calm that fight-or-flight response, allowing you to offer solutions that improve their experience.
👉 When a straightforward “yes” isn’t possible, Christine doesn’t lead with the truth or a flat “no.” Instead, she builds customer rapport and focuses on finding creative ways to assist them. Customers care less about the details of what’s possible and more about getting their needs met, and it’s our job in customer service to find ways to provide that.
👉 Legendary service isn’t just about cleanliness—it’s about making people feel special. Christine’s goal is to make regular people feel like movie stars and movie stars feel like regular people. Personalizing the experience is key, but it has to come from a place of genuine care. Legendary service only works if you truly believe in it and are committed to doing your best for your customers.

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Previous guests include: Luca Popovac, Senior Executive, Abhilasha Sinha of Open Secret, Laura Beavin-Yates, Stephen Griffiths of Level 2, Kristin Luck or ScaleHouse, Melina Palmer of The Brainy Business, Nicolas Zeisler of We’re Doing CX Wrong and How To Get It Right, Pricilla McKinney of Little Bird Marketing, Brooke Sellas of B Squared Marketing and Joseph Michelli of The Michelli Experience.
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