Storytelling vs. Story Selling: May the (Sales) Force Be With You

By understanding and implementing the art of storytelling, we can create that “Aha!” moment for our prospects. Getting to this moment of suspension will captivate your audience and strengthen your relationship. We should shift our focus from Am I going to close this deal? to Am I going to help this company achieve their goals?

Think about the last time you watched a movie or read a good book. Stories give us a chance to escape reality, if even for a short amount of time. Story selling should accomplish three goals:

  1. Did the story make the prospect think about their process?
  2. Did it help them view their problem in a new light?
  3. Will they share this story with their peers?

However, we have to do more than just live by case studies and the occasional fish tale — our prospects are smarter than that. It’s crucial to validate stories with data. A Forbes article tells us that we are 22 times more likely to remember a fact when it has been wrapped into a story.

Stories are not only memorable, but they tug on the heartstrings. Let’s shift focus away from B2C vs B2B and realize that every business interaction is H2H — or Human to Human. Building trust shows our prospects how each story and statistic is relative to their unique situation.

Writers study “voice” and how to reach unique audiences or personas. Often the solutions our companies provide affect multiple departments. Having a toolbox of bite-sized metaphors directed to each persona builds rapport — which is defined as the absence of differences. If you sound like your prospect (both your tone and your diction), your relationship will strengthen. When speaking to a Chief Marketing Officer, reference “voice of the customer,” a Chief Success Officer will resonate with a term like “adoption,” and the Chief Sales (or Revenue) Officer will understand how your solution relates to “pipeline.”

Four elements constitute every timeless narrative. One of the best stories of all time is Star Wars, so let’s break this down:


Let’s start with our hero. This person (or group) is inherently “good” but is typically dealt a bad hand. He/she will experience struggle and overcome obstacles to ultimately reach a destination. Luke Skywalker grew up on a farm; when his uncle purchased two droids, his life was forever changed. However, this opportunity did not come without adversity. The villain, Darth Vader, imposes evil actions that affect the plot and instigates obstacles to restrict his success.

Characterization in Story Selling

In a recent sales workshop at Sales Stack 2015, Juliana Crispo suggests that we position the customer as the hero.

“Every good sales story nowadays should cast the customer in the hero role. Customers don’t want to be ‘sold’ — they want to participate in how the plot unfolds. Focusing on features and benefits is tired and outdated. It’s the customer’s narrative and triumph over adversity that saves the day.” — Juliana Crispo, StartUp Sales Bootcamp

As for the villain? Not a person, but a problem — a lack of qualified leads, difficulty hiring quality talent, trouble understanding reporting — these are all “villains” in the sales galaxy.


When you hear, “in a galaxy far away…” you automatically think of Star Wars. If you can overlook the early-stage graphics and visual effects of the original series, the setting of Star Wars is intriguing because it is unknown. There is no doubt that the element of curiosity positively affected the success of this movie series.

Setting in Story Selling

Every company is unique, and we shouldn’t assume we understand their situation entirely. Providing industry-specific data and striving to educate our prospects is important for building trust, but we must seek first to understand and then to be understood. The most successful sales professionals have a commonality: trust-based relationships. Being actively curious will build trust and strengthen relationships with prospects.

Sherpa Software has heavy imagery in their messaging, and they have crafted a “story” that brings colorful imagery to their setting. When asked what they do they say, “We guide people as they try to manage mountains of data.” The immediate response is, “Like Sherpas!” Thus, Sherpa Software was born.


In Star Wars, Skywalker faces a decision to fight battles as a member of the noble Rebel Alliance or to give in to the dark side of the Force. While it would have been easier to join Darth Vader, he ultimately chooses the path of delayed gratification.

Conflict in Story Selling

Similarly, it’s not easy to make a decision on a solution that will change a company’s approach or strategy. However, without change, our prospect may be missing an opportunity to go from good to great. In Sandler Sales, we call this “pain.” As salespeople, it is our job to investigate this conflict and determine the factors that are holding our prospects back from exceeding their potential.


With Darth Vader’s sacrifice for his son, we reach a resolution — however the expanded universe does not simply end. The focus shifts and is heavily affected by the original characters, setting, and conflict.

Resolution in Story Selling

We complete a needs-based analysis, demonstrate value, and determine an agreement with our customers. After we close a deal, our job does not end. Customer success is an integral part of continuing the journey with your customer and molding your solution to continue to exceed expectations, even as new conflicts arise.

Choosing Your Stories

An easy way to determine which story to tell is by using an a la carte statement, which gives prospects a few scenarios that could be a current issue for them and aligns with your solution. Start a cold call or discovery meeting by saying, “Typically when I speak to someone in your position, they’re concerned with A, B, or C. Do any of those resonate with you?” If not, you’re either not speaking to the decision maker or your solution is not a good fit for the company. Dive into the issue they are experiencing and if your solution is not a fit, it’s better to part as friends than try too hard to fit a square peg in a round hole. On the other hand, if the prospect identifies with one or more of the issues — then tell a story that is relevant to their persona.

Client success stories are awesome. But our prospects don’t want to hear a fairy tale about a story in which they cannot be the hero. For example, I worked for a company called memoryBlue and often used this case study as a hook:

We helped build Eloqua’s #1 sales team, leading to their IPO and eventual acquisition by Oracle.

A Fortune 1,000 company might not care. But for a small, emerging software company, this story sets fire in their eyes and piques their interest enough to continue a conversation.

Take Your Places…Quiet, Please…ACTION!

Chris Ortolano, Conversation Systems Analyst and sales leader at, sheds light on action items that will improve your sales and story selling skills:

“Being goal-driven salespeople, we’re constantly focused on metrics and quotas. Instead, if we re-establish our prioritized goals, we can flip the funnel — putting customer success first on your list. Demonstrate value and build trust through storytelling, treating your prospects as if they are already customers.”
  • How often do you rehearse your selling story? “Winging it” is another villain for the heroic salesperson. Practice your stories, share them with your peers, gather and apply their feedback.
  • Do you have access to your call recordings? If so, do you listen to them? Recording and analyzing your “bests” and “worsts” helps hone the craft of storytelling. What’s working ? What’s not? Tools like KiteDesk will give you an opportunity for professional development with every meaningful reaction with potential buyers.
  • How often do you rewrite your sales stories? The best writers practice their craft by writing and rewriting every day. By rewriting your sales stories, you will inspire your prospects, create more “Aha!” moments, and build skills that help you accelerate as a sales leader.

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