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Early software mistakes and the “told you so” effect

Written by Luisa van Dongen | May 13, 2025

Choosing new software is usually a logical decision - driven by cost savings, better features, or long-term goals. But gaining support within the organization isn’t always logical. Once early issues appear - and they almost always do - skeptics are quick to react.

“I told you so.” This reaction isn’t just frustration - it’s a deeply rooted psychological response. In this article, we explain why small problems during a rollout can have a lasting impact and what you can do to handle them effectively.


Why small errors can have a big effect


Resistance to new software is expected. And while IT teams anticipate a few hiccups, users often see things differently. Even minor glitches can confirm their doubts. This is driven by confirmation bias - our tendency to focus on information that supports what we already believe.

That’s why skeptical users often treat small mistakes as signs the rollout is failing. Research shows people perceive change as a threat and instinctively notice flaws over benefits. This is especially true for executives, who depend on accurate reports. To them, even one wrong number can have serious consequences.

There’s also the negativity bias - people tend to remember negative experiences more vividly than positive ones. Even if most of the software works as expected, the few things that don’t will stand out the most.



💡 Three ways to manage early mistakes during testing

1. Set expectations around early challenges

Instead of promising a perfect rollout, prepare your team by explaining that minor issues are normal and will be resolved promptly.

2. Establish clear, fast support channels

Make sure no one feels stuck with a problem. Assign direct contacts for managers and key users to ensure quick feedback and reassurance.

3. Turn error reports into collaboration

Treat feedback as a vital part of the rollout process. Show users that their input directly shapes the system to fit their needs. This builds trust and encourages engagement.

It’s not the mistakes that create resistance - it’s feeling unsupported when they happen. The key is to manage expectations early and provide dependable support throughout the process.

An experienced software partner will help you stay ahead of these challenges. Find out how empower® can assist you with test planning and communication strategies that build user confidence - contact us.

In the next article, we’ll look at why a software change should never be framed as just a way to cut costs.