How to Win at 'Win-Loss' Storytelling
Here’s a tough truth about sales: Consumers don’t care about your product specs and service offerings.
What they care about is finding a solution to an issue they are experiencing in their life or business so they can resolve it and achieve their desired goals.
Effective business storytelling speaks to the customer through this lens and frames your product or service as a means for the “hero” (customer) to overcome their challenges and reach their goals. (see our 3D Story™ framework to learn more about this!). To do this well, you’ll need to deeply understand, through qualitative and quantitative data, exactly why a customer chose your company over its competitors as a part of their overall solution — in other words, how you fit into the customer’s personal story.
I recently had the opportunity to chat with Ken Schwarz, managing principal at PSP Enterprises, whose team conducts anonymous, peer-level interviews with a company’s prospects to analyze why they won or lost certain deals. Ken shared his insights on applying this win-loss data to storytelling and how other business leaders can use it to drive more effective storytelling efforts, both internally and externally.
What is a ‘win-loss interview’?
One big sales mistake most companies make is assuming that they are the solution to a customer’s problems, when in reality, there are countless external factors and points along the buyer’s journey that influenced their final decision. When these companies win a deal, they tend to ignore all those other factors and don’t truly learn anything about why their product or service was in the right place at the right time for this customer. When they lose a deal, they might only look at a single dimension, like price, as the only reason the customer didn’t buy, without considering any of the context surrounding that decision.
That’s where professionals like Ken come in.
“What we do is we call up the customers of our clients after their deals are won or lost,” he explains. “We talk to them blind and anonymous so ... the person we're talking with doesn't know who we're working for. And ... we try to get as unbiased a read [as possible] on how and why they made the decision that they did.”
Conducting a win-loss interview has numerous benefits, and doing it anonymously helps put customers and prospects at ease when sharing what might be critical feedback about your company. There are three key things that Ken and his team cover when conducting these interviews:
What were the criteria the customer used to make their decision?
Why were those criteria important to them?
How did they size up their choices?
“We find out the very particular reasons why the customer came to the opinion that they did, [and] what series of impressions and perceptions and experiences led to that decision,” said Ken. “Then, we relay those findings back to our clients so ... they're able to understand better how they can affect [customer] outcomes in the future to their benefit.”
Running a win-loss analysis provides businesses with the insight needed to improve their products and services, sales approach, and more. When you have the right information directly from the source, you can create a better marketing and messaging strategy for both your team and your audience.
How ‘win-loss’ data fuels great storytelling
One crucial point I’d like to highlight from Ken’s insights is this idea of customer perceptions. Perception is reality when it comes to decision-making, and as a customer goes through their buying journey, they develop a certain perception about the solution they believe will be best for their needs.
Controlling that perception is key: If you don’t make a proactive effort to control the market’s perception of your brand — if you don't have a strategic narrative or positioning and messaging framework — then you’re rolling the dice on whether a customer will view you as part of their solution.
“You're … setting yourself up for some disaster if your competition tells your story for you, and that's what can happen if you're not aware of how the competition operates, and if you're not prepared to counter some of the stories they might be telling about you,” says Ken.
So how do we, as marketers and salespeople, create an experience and invest in the right messaging and communications to influence the customer’s perception? The answer is by applying win-loss data to your storytelling efforts.
“Win-loss storytelling” involves taking information from win-loss interviews conducted with your customers and using that data to better shape your own narratives. Without win-loss, you’re leaving a huge piece of the storytelling puzzle out, as this data helps you understand how the scales are tipping from a value perspective. Understanding where your value lies is crucial to creating your story.
“When [win-loss storytelling] is done well, it's an overwhelming advantage,” says Ken.
How to win at win-loss storytelling
Ultimately, storytelling is a value-solving problem. Incorporating important insights from your win-loss data can help you hone in on that unique value and better communicate it to your customers. Here are a few specific tips to help you win at win-loss storytelling:
Understand your audience
When working on strategic narrative projects, you must meet your customers where they are and dig deeper to discover their morals, essential emotions, and truths — the essentials of forming a good story.
“These things aren't that hard to find out, but you do need to talk to the customers in order to find them out, because they're abstract enough and subtle enough that people can get it all wrong if they don't actually go to the source,” says Ken. “Just talk to them and find out where their hearts lie. What are their real concerns? … When you have that, the storytelling [isn’t] very complicated.”
Let customers know you care
When telling their stories to consumers, many businesses will focus more on their own background, trying to convince their audience they’re the best business on the market rather than focusing on their customers as humans.
“The default thing is to communicate to the prospective customer your company's story about your founders and their credibility, about your backing VCs, and how terrific your technology is,” Ken notes.
But especially for younger companies up against blue-chip competition, this isn’t nearly as effective as what the best companies do: Getting the head of sales, the CEO, and/or board members to speak directly with the customer to form a relationship.
“If they do that, what I hear in the [win-loss] interview … is that specific experience about how the respondent got on the phone or met directly with the CEO, and believes that that person will stand up for them … [and] that they will be taken care of,” said Ken. “And that that was what they will base their decision on more than anything else.”
By involving executives and getting personal with your customers, you’re essentially telling them you care about them, ensuring the stories you share involve them, too.
Strive for value alignment
Storytelling is more than just the act of telling a story. “Telling” is just one small part of the human experience of story, which also involves planning, making, and remembering powerful stories. Armed with data from your win-loss interviews, you can partake in story-making — that is, co-creating an experience with the customer that makes them want you and your brand to be a part of their own story.
The way to do this effectively is by using storytelling to create value alignment. Customers want to know that the company they’re buying from supports their values and vice versa.
“There's a certain degree of strategic alignment or value alignment that [customers] perceive about the vendor that they're working with that makes them more of a partner rather than a supplier,” says Ken of “won” deals. “[This] is communicated by the reputation and the values that come through in all the communications of the vendor.”
Getting in the habit of conducting or coordinating win-loss interviews with your sales prospects can feel strange at first, but it’s an important part of understanding the unique value you provide your customers. By understanding this essential piece of the sales and marketing puzzle, you can tell better, more powerful stories that persuade more customers to choose your company as part of the solutions they seek.
Ready to dive deeper into your customer data and use it for better business storytelling? Book a complimentary consultation with Go Narrative to learn more about our storytelling tools and frameworks.

