What are your failure and success stories from your storytelling efforts?

Knowing success is easy. It’s when you go to a conference and you see and hear your sales reps, prospects, and customers repeating the messaging. It’s when your leadership is on stage delivering the narrative that you’ve spent months working with the comms team, sales team and others crafting. You know what that feels like. Failure is harder to pin down. We tend to want everything instantaneously, so if it feels like a message didn’t resonate the first time you tried it out, you might be tempted to call it a failure and start over. But some things need repetition to stick and all of us need practice and more reps to get better at delivering the message. So I’d say the failure stories are typically part of the eventual path to success. It’s never binary, one or zero. It’s part of the process of getting the messaging perfected.

I have two to share ---

Failure Story: Overly Technical Messaging

Context:
We were launching a highly technical, proprietary solution focused on automating complex workflows for enterprise customers. Our initial messaging centered on the advanced capabilities of the automation engine, emphasizing its speed, precision, and underlying technology stack.

What Went Wrong:
The messaging didn’t resonate with the target audience, as it was too focused on technical details and lacked a clear connection to the customer’s needs. The story we told was product-centric, filled with technical jargon, and didn’t explain how it would make life easier for the end users. As a result, prospects felt overwhelmed and disconnected from the benefits, leaving us with minimal engagement.

What I Learned:

• Lead with outcomes, not technology: While technical superiority is important, the audience cares more about how it affects them—whether it simplifies processes, reduces manual errors, or improves operational efficiency. We needed to communicate that in simpler, more practical terms.

• Make the story relatable: The initial approach alienated users because they couldn’t relate to the deep technical specifics. We should have used examples or scenarios that mirrored the everyday problems our solution solved for them.

Success Story: Customer-Centric Storytelling

Context:
In a later campaign, we pivoted to focus on real-world outcomes, showcasing how our solution improved operational efficiency by automating repetitive tasks. The messaging was built around relatable pain points—teams spending too much time on manual processes, missing deadlines due to human error, or struggling with system integration. We highlighted customer success stories that demonstrated how using our platform reduced errors and streamlined workflows.

What Went Right:
We told the story from the customer’s perspective, showing the specific challenges they faced before implementing our solution, and how it positively impacted their daily operations—without overwhelming them with technical details. By focusing on their journey, we illustrated how the product fit seamlessly into their existing workflow, simplifying tasks and improving accuracy.

What Worked:

• Humanize the problem: By speaking to common frustrations—like manual data entry or errors in complex processes—we made the story relatable. Prospects could immediately see themselves in those scenarios.

• Tangible results: Instead of abstract technical features, we showcased outcomes like "reduced manual tasks by 40% in the first month" and "cut processing errors by half." These numbers grounded the narrative in results that mattered to them.

• Simple, clear messaging: The focus on practical benefits and easy-to-understand examples made the story accessible to both technical and non-technical audiences.

What I Learned:

• Customer-first storytelling: Shifting the focus to how the solution improves daily operations for end-users makes the narrative far more compelling.

• Clear, actionable results: Providing specific, quantifiable outcomes helps build trust and provides a clear sense of the solution’s impact on workflow improvement.

Takeaways:

• Failure results when messaging gets lost in the technical weeds and doesn’t connect with the audience's daily challenges.

• Success comes when you simplify the story, focusing on real-world outcomes that your product enables, while making it easy for prospects to relate to those challenges and see the value.