Hidden costs are the primary reason for software purchase regret
Software buying decisions should be simple: identify the best tool, evaluate the cost, and integrate it seamlessly into operations. But the reality is often far messier. Many companies think they’ve landed a great deal—until hidden costs start stacking up. They’re deal-breakers that turn what seemed like a smart investment into an expensive lesson.
Hidden costs show up in different ways: licensing fees that increase with scale, mandatory upgrades that weren’t in the original budget, or additional costs for onboarding, training, and long-term support. The problem? These costs often aren’t obvious until after the purchase. And by then, it’s too late. The budget is already stretched, and the return on investment (ROI) starts looking questionable.
According to Capterra, 57% of UK software buyers regretted at least one purchase, and 34% pointed to unexpected costs as the main reason. It’s a systemic problem. Companies that don’t account for these variables in their decision-making process risk paying far more than they originally intended.
The takeaway is clear: software buyers must demand transparency. If a vendor isn’t upfront about total costs—including licensing structure, implementation fees, and long-term expenses—then either they don’t understand their own pricing, or they’re deliberately avoiding the conversation. Neither is good.
Software complexity and onboarding challenges
A software product can be packed with powerful features, but if people can’t figure out how to use it efficiently, it becomes more of a burden than an asset. Complexity kills adoption. And poor onboarding means a longer learning curve, wasted productivity, and ultimately, regret.
The problem here isn’t that businesses don’t want advanced features. It’s that complexity without usability is pointless. If a system is too confusing, employees will resist using it or find workarounds—often leading to inefficiencies and lost time. Training can help, but only if it’s built into the rollout process. Many companies overlook this step, assuming users will “just figure it out.” They don’t.
In Capterra’s research, 30% of regretful buyers cited complexity as a major issue, and the same percentage struggled with training and onboarding. That’s a big deal. If nearly a third of companies can’t get employees up to speed, then the software isn’t solving problems—it’s creating them.
“The best approach? Before signing a contract, test usability with real users, and not just IT teams. If employees struggle in a trial setting, things will only get worse in a live environment. And if a vendor isn’t willing to invest in onboarding, that’s a red flag.”
Poor integration with existing systems and slow setup processes
No company operates in isolation. Every business already has a tech stack—finance tools, CRM systems, productivity platforms, and more. New software has to fit into this ecosystem smoothly. If it doesn’t, the results are messy: data silos, inefficiencies, and teams wasting hours trying to make incompatible systems talk to each other.
The problem? Many software vendors don’t prioritize integration. They focus on their product in a vacuum, assuming that businesses will figure out how to make it work. That’s a flawed assumption. If a tool can’t easily sync with core business functions, then it doesn’t matter how impressive its features are. It becomes a liability.
Capterra’s data backs this up—29% of regretful buyers cited integration issues, and 28% mentioned slow or difficult setup. When a system doesn’t fit, businesses have two choices: invest heavily in customization or scrap the software altogether. Either way, it’s costly.
The lesson here is simple: before buying, integration should be tested, not assumed. If a vendor can’t demonstrate seamless compatibility with existing tools, that’s a red flag. And if the setup process is vague, expect delays.
Financial losses, reduced productivity, and security risks
Software is an investment, and like any investment, the right choice delivers returns. But when businesses pick the wrong tool, the losses extend beyond the purchase price. It impacts operations, security, and even revenue.
First, there’s the financial hit. Companies that regret their software purchases face additional costs fixing the issues caused by their bad investment. According to Capterra, 56% of regretful buyers reported increased costs as a direct consequence of their decision.
Then there’s productivity. When software doesn’t work as expected, employees waste time managing inefficient processes, dealing with errors, or waiting for IT to troubleshoot issues. This is why 42% of regretful buyers reported reduced productivity.
But perhaps the most serious issue is security. Poorly chosen software can introduce vulnerabilities that put sensitive company data at risk. According to the study, 35% of regretful buyers experienced security-related issues. And in today’s world, a single data breach can cost millions—not just in direct losses, but in reputational damage.
“A bad software decision is an operational risk. Companies need to evaluate software based on long-term impact, not just short-term pricing. If a vendor can’t guarantee security, efficiency, and scalability, then the real cost may be far higher than expected.”
Inadequate research and rigid shortlisting
The biggest mistakes in software buying don’t happen after implementation—they happen before the purchase. Too many companies rush decisions, relying on limited information, and narrowing their choices too soon. The result? A higher risk of picking the wrong tool.
Capterra’s study found that regretful buyers were less likely to do their homework. Only 59% created a shortlist of potential vendors, compared to 72% of successful buyers. That’s a significant gap. Even more revealing: 22% of regretful buyers stuck to their original shortlist, versus just 17% of those who were satisfied with their purchase.
What does this mean? Flexibility matters. The most successful software buyers adjust their approach as they gather more information. They don’t lock in decisions too early, and they don’t let assumptions drive the process.
Smart buyers also expand their research beyond vendor claims. Industry experts, customer testimonials, and unbiased review sites provide critical insights that sales teams won’t mention. The best companies prioritize this type of information—and it shows in their results.
The takeaway is simple: the more effort put into research, the lower the chances of regret. Companies that remain flexible, open to new options, and committed to rigorous evaluation make better decisions. And in a world where technology is a competitive advantage, that’s everything.
Thorough research using expert reviews and customer testimonials
The difference between buyers who regret their decisions and those who don’t often comes down to how much research they did before signing the contract.
According to Capterra, successful software buyers looked beyond the sales pitch. 56% sought insights from industry experts, 48% examined customer testimonials, and 47% used product comparison websites. That’s a pattern. The more sources of information, the better the final decision.
Why does this work? Industry experts provide a high-level view of trends, best practices, and pitfalls. Customer testimonials give real-world feedback, showing how the software performs in practice, not just in a demo. And review sites offer side-by-side comparisons, making it easier to cut through marketing noise.
The key takeaway here is that buying software without outside input is a high-risk move. Vendors will always highlight the best-case scenario. That’s their job. Yours is to figure out what’s missing from the story before making a decision.
Product trials significantly reduce the likelihood of regret
Too many companies skip this step and rely on demos or marketing materials instead. That’s a mistake. A hands-on trial is the only way to see if the software actually works the way you need it to.
Capterra’s research shows a clear trend: 72% of successful buyers ran full product trials before purchasing, compared to just 51% of those who regretted their decision. That’s a major difference. The companies that take the time to test their options are far less likely to end up with buyer’s remorse.
Why? Because real-world testing reveals the hidden problems that sales pitches won’t. It uncovers clunky interfaces, unexpected limitations, and integration challenges before money is spent. More importantly, it forces vendors to prove that their product can actually deliver.
A live trial also gives employees a chance to interact with the software, not just IT teams. If end-users struggle during testing, that’s a red flag. No amount of onboarding or training will make up for bad design.
“The best strategy is simple: if a vendor isn’t willing to offer a full test run, move on.”
Clearer goal definition and improved stakeholder communication
If you don’t know exactly what problem you’re solving, no software will fix it. One of the biggest reasons software projects fail is that businesses jump straight into the buying process without first defining their goals.
33% of regretful buyers in Capterra’s study admitted they should have clarified their goals before making a decision. That’s a big admission. Without clear objectives, businesses risk buying software that looks impressive but doesn’t actually meet their needs.
31% of regretful buyers said they needed better stakeholder communication. This makes sense. A software tool might be a great fit for IT but a disaster for end-users. Or vice versa. If key departments aren’t involved in the decision-making process, the software may end up being a misfit from day one.
The smartest buyers take the time to define what success looks like before even shortlisting vendors. They set clear performance benchmarks and make sure every department that will use the tool has a say. The result? Fewer surprises and a much higher chance of long-term success.
Learn from successful buyers to improve future decision-making
Like any process, some companies do it better than others. The smart move? Learn from the ones who get it right.
According to David Jani, UK Analyst for Capterra, companies should study the buying strategies of successful businesses just like they analyze competitors’ marketing or sales tactics. That’s an important mindset shift. Instead of just reacting to bad purchases, businesses should proactively model their approach on those who consistently get it right.
What do successful buyers do differently?
- They do their homework—digging into expert reviews, customer testimonials, and third-party comparisons.
- They stay flexible—adjusting their vendor list as they gather more information.
- They test everything—never committing without a real-world trial.
- They communicate internally—ensuring every stakeholder is aligned before the decision is made.
“The companies that make smarter software decisions move faster, operate more efficiently, and scale without constant IT headaches. In the long run, that’s what separates industry leaders from everyone else.”
Final thoughts
Bad software decisions cost money, time, and momentum. But they’re avoidable. The companies that win in the long run are the ones that take a disciplined approach—doing the research, staying flexible, testing before buying, and making sure every purchase is aligned with clear business goals.
Technology should be a multiplier for success, not a drain on resources. The best software isn’t the most expensive nor the most hyped—it’s the one that seamlessly integrates into your business and makes operations more efficient.
Approach software buying with the same mindset as engineering: test, iterate, and optimize. That’s how you make decisions that stand the test of time.
