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Your Error Message Is Losing You Customers—Here’s How to Turn It Into a Loyalty-Driving Conversation 

 September 1, 2025

By  Joe Habscheid

Summary: A simple error message can reveal more about system design, customer relationships, and business psychology than a dozen user manuals. What looks like an insignificant JSON string complaining about account balance is actually a case study in user experience breakdown. It tells us where assumptions failed, where friction grew, and where an opportunity to build loyalty was missed. Learn how this small gap in messaging impacts behavior, and what professionals—and service providers—must learn from it.


The Message That Wasn’t Meant to Sell—But Did

Let's dissect the “error message” in question: A response from a web service telling the user their account balance is too low to process their request. Accurately, the JSON output doesn’t contain human language meant to persuade or inform—it’s machine-readable. It gives no guidance, builds no trust, and assumes the user knows what to do next: recharge.

So what’s the problem? The absence of structure. The loss of a vital human-to-human communication moment in a transactional, automated slip. A perfectly coded error with perfectly missed persuasion.

Every Message Is a Marketing Moment

Even technical messages tell stories. When a user receives “insufficient funds,” they’re not just being informed—they’re being told: “You didn’t plan properly” or worse, “You don’t belong here.” Rational or not, the emotional response is there. And if that message is cold and devoid of empathy, the business just created friction, not loyalty.

How often does your system talk to your user without you? What tone does it take? More importantly, what assumptions is it making about your user’s knowledge, mindset, and priorities? Those assumptions have consequences. And most of the time, no one’s watching.

A Missed Opportunity for Reciprocity

Robert Cialdini’s principle of Reciprocity tells us people feel compelled to return favors. But what if the system never offers one? A user tries to query data, hits a wall, and all they get is a binary rejection. What if instead of “you’re out of money,” the error explained what could be done to reduce usage, or even offered insight that saved the user time or money?

That would build goodwill. And goodwill builds stickiness. A simple change like “Your balance is low—want to review your previous 3 queries and optimize your usage?” suddenly transforms a stone wall into a helpful hand. That’s persuasion through value. That’s how users stay.

What ‘No’ Really Means in User Communication

Chris Voss argues “No” is not the end of a conversation—it’s the beginning. In this case, the system says “No, your account can’t process this query,” but gives no chance to respond. No context. No redirection. No incentive. Strategic silence is helpful in human negotiation—not in a machine coldly shutting the conversation down.

What would happen if the error was followed by: “What data are you trying to access?” or “Would you like a smaller query that fits the current balance?” By creating an opening for dialogue—even automated—users feel heard. Their autonomy is respected. One more reason to stay, one less reason to abandon.

The Psychology of Transactional Failure

Let’s go further. The user may already be feeling vulnerable—perhaps they’re a startup strapped for cash, or a student learning the ropes. This rejection confirms their inner fear: “You can’t afford this.” But the right message could flip that: “You’re close. Just a top-up away. Keep going.”

Empathizing with the user’s struggle changes the game. Instead of punishment, the message becomes encouragement. This is what Blair Warren meant by confirming the audience’s suspicions while encouraging their dreams. The user believes tech is ruthless and unforgiving, and the platform just confirmed it—unless we rewrite the story.

Authority Doesn’t Mean Arrogance

Systems are built by experts. But systems that serve are built by communicators. You’ve got deep technical skill? Good. Now show you’ve also got compassion and intelligence in the way your tool talks to users. That’s real authority. When people say, “This tool gets me,” they stick. And they talk about it. That’s social proof.

Want to keep churn low and referrals high? Start with the messages no one ever reads—because the recipient always does.

Build from Commitment and Consistency

Users already made a choice to trust your platform. They signed up, they input data, they ran queries. That’s behavioral commitment. But when something goes wrong, they need a clear path forward or their loyalty evaporates. The error message should reinforce their original decision: “You’re on the right path. This is just a step. Recharge and let’s keep going.”

That ties into their identity as someone persistent, decisive, resourceful. If your system treats them like a failure for hitting zero balance, they’ll retreat. But help them reaffirm their commitment, and you bring them back stronger than before.

The Fix Is Simple, But Not Easy

Rewriting error messages costs almost nothing. But it takes empathy. It takes someone in your org saying, “What does this phrasing say about us?” and more importantly, “What does this phrasing make the user feel about themselves?”

Do users feel guided or deserted? Shamed or supported? Is the message transactional, or relational?

None of this happens by accident. And if it’s not thought through, your platform probably says things your leadership would never say out loud—because you let the code speak instead of the brand.

Rewriting the Micro-Conversations That Drive Behavior

Any customer interaction is a micro-conversation. Every one has an Interrupt, Engage, Educate, and Offer structure embedded—even in error logs.

  • Interrupt: The error message grabs attention.
  • Engage: The phrasing acknowledges the user's situation.
  • Educate: The message explains what happened and why.
  • Offer: Suggests what to do next—whether user support, a smaller query, or an easy recharge option.

Your worst moments—bugs, failed payments, limitations—are trust-building opportunities if you frame them correctly. That’s the deeper lesson.

Use the Friction

Error messages are friction. But friction can create traction if used properly. Don't polish away every difficulty—people don’t value what comes with zero effort. But show them you're with them at every friction point, and now they’re not just tolerating the friction—they're working through it with your help.

Even a simple JSON response can be either a dead-end or a trust checkpoint. What kind of company do you want to be known as? The one that throws a technical wall—or the one that talks like a partner, even when things go wrong?

Make your software speak like your best support rep. Precise. Helpful. Empathetic. Forward-moving.


#UXMatters #CustomerRetention #ErrorMessaging #MarketingWisdom #UserFirstDesign #BehavioralScienceInTech #IEEOMarketing

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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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