Welcome to the Winning the Challenger Sale (WTCS) webinar series, currently in its third season. With host Jen Allen, WTCS’s webinar invites sales professionals and commercial leaders to join lively and informative conversations inspired by the Challenger™ Sales Methodology playbook. Sellers, managers, coaches and sales leaders get practical advice and actionable insight for the day-to-day skills and behaviors that win in complex selling and buying environments.

EPISODE 5 Recap: Persuasive Storytelling

In this month’s episode of WTCS, “Persuasive Storytelling,” Jen Allen talks about how storytelling elicits emotions and the ways sellers can effectively spark those emotions in the selling process. “Logic makes us think. Emotion makes us act,” she says.

The Story Behind Persuasive Storytelling

On average, only 49 percent of customers who are willing to buy from a supplier are also willing to advocate for that supplier within their organization. The failure here for many sellers is that too often we make our company or our solution the hero. The best sellers know that we win deals when we center the experience around the buyer and invoke a human, emotional response throughout the buying process.  

Customers need to imagine themselves as an active participant in the narrative, either creating demand with problem stories or activating demand with solution stories.

In early-stage sales conversations, how often are you spending the majority of your time “pitching change” vs. “deepening the pain?”

Effective Storytelling

In sales, we recommend three steps to effective storytelling:

  1. Isolate your purpose. The story should match what you want your customer to feel.
  2. Build your three key story elements. Give them someone to cheer for. Your audience should be able to see themselves in the main character.
  3. Structure your three-part story arc. Know the steps and guideposts you need to hit.

It’s important to note: Only 5 to 10 percent of information containing facts and statistics will be retained, while the retention rate of using stories and anecdotes rises to 60 to 75 percent.

Here are Jen’s key takeaways from the “Persuasive Storytelling” episode of WTCS:

  • Stop making your company and solution the hero and instead start identifying that emotion you want your customers to feel.
  • Stop overleveraging “solution” stories and underleveraging “problem” stories and instead be more diligent about identifying: who is the character and what is the imagery I need to get through? Use the framework for your situation, complication and outcome while reinforcing the cost of inaction.
  • By virtue of having a common conversation choreography, there’s no reason why you can’t tap into your network to find out how they are creating emotional impact to tell better stories.


The next WTCS webinar, which is on the second Thursday of every month, is “Turning Interest into Advocacy.” It will air live on July 14, 2022. Register for this episode and the full series here.  

To watch the full episode, “Persuasive Storytelling,” view it here

Want more ideas on how to win the sale? Catch the latest Winning the Challenger Sale podcast here. Recent guests include Ravi Rajani, Brent Adamson, Nick Capozzi (6/14) and Doug Ferreira (6/21). 


Challenger is the global leader in training, technology, and consulting to win today’s complex sale. Our sales transformation and training programs are supported by ongoing research and backed by our best-selling books, The Challenger Sale, The Challenger Customer, and The Effortless Experience.