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Once Upon a Sale

Why Hustlers Use Storytelling to Close More Sales

3/28/2025 | The Hustle

Storytelling (noun): The art of telling and sharing stories that engage an audience through emotion and empathy.

“When I got to his office, I heard the panic in his voice. He was told top executives from the corporate office were coming for a surprise visit and he needed to provide some high-end, personalized gifts in just three days. He called me because he’d struggled with another vendor in the past, but  heard I’d helped others in his department with quick turns and unique products. I offered a few ideas we could personalize quickly, he picked one, and I had them back to him in two days, and under budget. I helped him look good and he received accolades from his boss for the outstanding work.”

That’s a sales story and for as long as humans have walked the earth, storytelling has been used as a way to captivate audiences and share information. In the world of sales, hustlers understand storytelling can be a powerful tool if used correctly, and it can help persuade potential customers to purchase your products or services.

Some of the best storytellers in the business world captivate our imaginations and lead us to believe in something bigger than ourselves. Steve Jobs didn’t create the first mobile phone, but when he launched the game-changing iPhone, he used stories to share his vision. Sir Richard Branson, founder of the Virgin Group of businesses, tells swashbuckling stories to connect people to the rebellious spirit of his brands. Walt Disney created timeless characters and worlds that helped shape our modern world of entertainment, while Oprah Winfrey built her media empire through deeply personal and relatable stories. And author, motivational speaker, and philanthropist Tony Robbins uses engaging stories built on his struggles growing up and what he’s learned in the ensuing years. 

Some of us tell stories better than others; however, it is an art that can be learned. Below are some basics to help you improve your storytelling capabilities on sales calls.

  • Know your audience: In sales, your audience could be one person or a roomful of people. The key is to use language and scenarios the people you’re speaking with can relate to. Do your homework beforehand to understand their pain points, their goals, and the challenges they face in their businesses. Are they younger or older, what industry are they in, and what keeps them up at night? A study by cloud-based presentation software Prezi showed 55% of people say a great story captures their imagination and keeps them engaged. By understanding your audience, your stories become relatable and engaging. 
  • Structure your stories: While the best stories might seem off-the-cuff, they all have a structure that makes them engaging. For example, this structure is found in the books we read, the songs we listen to, and movies and plays we see. And is used by anyone who wants to enthrall their audience. The structure includes these details:
  • A Hero – A customer or someone else relatable to your audience.
  • The Problem – The challenge or pain point your hero faced.
  • The Journey – How your hero tried to solve the problem on their own and struggled.
  • The Solution – How your product or service helped them solve the challenge they faced.
  • The Success – The positive results they achieved as a result of using your product or service to solve their challenge, makes the perfect ending to your story.

If you go back to the short story I told at the beginning of this post, you’ll find each of these elements are part of the narrative. Create structure to captivate your listeners.

  • Use case histories, success stories, and testimonials: Data can be boring by itself, but a case history or success story incorporating data points can be very effective. Throw in some humor, be enthusiastic, and use these stories to bridge the gap between your product and service and their impact with real-world customers. Ask questions, even if you already know the answer, and use their response to lead into a story to clarify their concern or enhance your offerings. Take the advice of Annette Simmons, expert storyteller and author, “People dont want more information. They are up to their eyeballs in information. They want faith — faith in you, your goals, your success, in the story you tell.”
  • Keep your stories concise and short: My dad passed away many years ago, but bless his heart, he loved to tell stories. LONG stories with every detail he could think of. When he was done, my mom was usually asleep, and my eyes had long ago rolled up into my head! The point is, keep your stories succinct and on-point. Artfully incorporate them into your pitch to enhance the conversation and engage your customer, not bore them to death. This harks back to some of the best advice I ever learned early in my sales career; listen 80% of the time and talk 20% of the time. Make sure your stories are short, tie-in with the conversation, and lead your customer to understand how your services and products can solve the challenges(s) they face.
  • End with a takeaway that leads to a call to action/close: Even the best stories might not lead your prospect to buy what you’re offering. A call to action, or CTA, is a confident and direct request that creates a sense of urgency and value. Without a CTA, your customers might be interested, but not sure what to do next. Use stories in your pitch to lead the conversation to a call to action, using the facts you’ve uncovered in your research. Are they motivated by fear, a sense of urgency, the need for compliance, or even a boost to their status? Stories that tie into these needs along with a strong CTA showing the benefits of making a decision today will lead you to close more sales that benefit your customers. 

Hustlers understand how emotions play a significant role in the sales process and the way stories help build trust with your prospects and customers. People buy from people they trust, and authentic storytelling humanizes you and makes the sales process less salesy.

Entrepreneur, author and Internet personality Gary Vaynerchuk says, “Storytelling is by far the most underrated skill in business.”  If you want to stand apart from your competition, use authentic stories in your sales pitches, stories highlighting the value of working with you and your company.   

Practice your storytelling skills and keep a variety of stories in your sales toolbox to build connections and stimulate the imagination of your customers. Don’t bore them with a list of features and benefits, show them how those benefits and features have solved the problems of prospects just like them. 

Ready to make your sales pitches more engaging, memorable, and persuasive? Then practice what our ancient ancestors did long before the written word, tell stories that resonate with your customers and prospects. And if you do this well, chances are you and your customers will live happily ever after!!


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