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If Your Error Messages Sound Like Robots, You’re Losing Customers—Here’s Why 

 October 24, 2025

By  Joe Habscheid

Summary: System messages that seem trivial—like a JSON error about “insufficient account balance”—might feel like throwaway alerts. But when we slow down and truly consider the structure, the frustration behind the screen, and the loss of progress that these messages represent, they carry a richer story. A missed opportunity. A halted process. A real human moment obscured by machine language. Let’s explore how this type of system message reveals much more than tech clutter—it’s a red flag for businesses, developers, and marketers alike.


The Real Message Behind “Insufficient Account Balance”

The specific line in the prompt—“I apologize, but the provided text does not appear to be a raw website text containing a story that needs to be extracted and rewritten…”—was generated in reaction to a JSON error, likely caught in a content processing system. On one hand, it’s technical accuracy. On the other, it’s a moment where a user—possibly a customer, a prospect, or a team member—just hit a wall.

And not just any wall—a wall with zero explanation that helps them move forward. This matters. Because these small moments of friction compound. Every time a system reacts like this without empathy or solution, it tells the user: “You’re on your own.”

Error Messages Are Part of Customer Experience

Too often, we delegate error handling to developers and push them out with default language that’s technically true but emotionally sterile. What’s missing? Empathy. Clarity. Direction. Chris Voss teaches that friction points are negotiation moments. When someone hits an error, you have an open door to either build trust—or destroy it.

What would it look like if instead, the message mirrored what the user might be feeling—frustrated, unsure, probably questioning whether they did something wrong? What if it paused to clarify and offer them an out?

This isn’t about dressing things up with fancy words. It’s about meaningful messaging when things go wrong. What would it take for an error to sound more human? Something like:

  • “It looks like there’s a problem with your current balance. Can you check your account settings or payment method?”
  • “We couldn’t continue because of a balance issue. Would you like help resolving it?”

These messages do three critical things: they mirror the situation, invite dialogue by asking questions, and acknowledge the user's emotion without judgment. They use Chris Voss’s framework without needing to reference negotiations at all. Human connection is the negotiation.

This Isn’t Just a Dev Problem

Marketing teams, product designers, and business leaders need to care about this kind of messaging. Why? Because it tells your user how seriously you take their experience beyond the glossy homepage. Does your product vision extend to what happens when things break? Do you lead with clarity, or do you default to silence?

If a paying user can’t do what they need to because of a balance issue—especially if they didn’t expect it—it’s your business, not just your code, that has a credibility problem. “Insufficient balance” is rarely the root issue. It’s often a failure in transparency, timing, or user education.

How Many People Just Gave Up?

When this type of error surfaces, we should stop and ask: how many users bounced? How many found a competitor and never looked back? How many support tickets were never opened, and how many problems went unresolved because your system lacked the language—and empathy—to encourage engagement?

And if this is your internal team hitting that wall—a freelancer, an assistant, a partner agency—what message did you just send them about your systems and culture?

Rewriting This Moment: Why the Words Matter

Let’s go back to the original system output:

“I apologize, but the provided text does not appear to be a raw website text containing a story that needs to be extracted and rewritten. The text seems to be a JSON response with an error message related to an insufficient account balance.”

This response is technically precise. But think about who reads this and when. It doesn’t ask the next question. Voss would know that’s a dead end. Powerful communication always leaves room for response. It invites engagement with a simple but specific open-ended question:

  • “What are you trying to accomplish with this content?”
  • “Do you want help resolving the output?”

When you open space for the other party to say “No”—or even “That’s not what I mean…”—you keep the dialogue alive. That’s where real problem-solving starts. That’s how loyalty is built, one mishap at a time.

What’s Next: Systems That Speak Human

Every error message is a reflection of a system’s design priorities. Is the system built to correct, or to collaborate? Is your communication strategy only active during ideal user paths – or also during chaotic, interrupted, frustrating ones?

If your automated messages don’t mirror your customer’s state of mind, you’ve missed a chance to stand out. If your tech stack doesn’t reflect your brand voice in the ugly moments, your users won’t trust your message when you pitch during the sunny ones.

And if your team writes system copy without marketing, product, and support folks at the table—it’s time to rethink your priorities. Good software is incomplete without good language.

Own the Broken Moments

This post is not about JSON. Not really. It’s about ownership. Error messages are your quietest marketing strategies—either building confidence or subtraction by a thousand tech cuts.

So ask yourself: what error message is your user most likely to see? Is it an alert dressed in blame, or a prompt that guides, invites, and reflects their state of mind? The answer is not just in better UX. It’s in better thinking. Better leadership. And better respect for the dialogue you’ve started with everyone who trusts you enough to log in.


#SystemDesign #UserExperience #MarketingMessaging #HumanizeTech #CustomerTrust #ChrisVossTactics #BusinessResponsibility #ClarityMatters #ErrorCommunication

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Featured Image courtesy of Unsplash and Markus Winkler (-q8MdTL2998)

Joe Habscheid


Joe Habscheid is the founder of midmichiganai.com. A trilingual speaker fluent in Luxemburgese, German, and English, he grew up in Germany near Luxembourg. After obtaining a Master's in Physics in Germany, he moved to the U.S. and built a successful electronics manufacturing office. With an MBA and over 20 years of expertise transforming several small businesses into multi-seven-figure successes, Joe believes in using time wisely. His approach to consulting helps clients increase revenue and execute growth strategies. Joe's writings offer valuable insights into AI, marketing, politics, and general interests.

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