I spent months comparing banking software before I could name the problem

We spent months talking about switching our banking software. I had an IT service company in Hamburg, Germany, for over 20 years. At some point, the program we were using for our payments and bank statements started becoming the bottleneck. We researched and did demos like most small companies do.

In the end, we stayed with the same program. The problem we actually had was much smaller. Our bank statements were in that program and no other system in our company could access them. We exported them to a network drive on a daily basis in cash management (CAMT) format, which is commonly used for electronic bank statement files in Europe. Our other programs could then read these files. The solution took 15 minutes.

I think about this often. It's such a simple mistake. We researched software before we identified the problem we had. I believe this is the most costly way to do things.

Regret is common

Research shows that as well. Capterra surveyed financial services companies in their 2025 Tech Trends report. 70% of respondents had regrets about a software purchase in the last 18 months according to Accounting Today in 2025. The most common product-related reason among respondents who regretted a purchase was that the software was too basic for their needs, at 35%.

I think this can happen when a customer says a piece of software is too basic. They may have found a need that they didn't list when purchasing the software. The software did what they were shown but no one identified what they needed it to do.

Write the question down first

Now when I'm looking at any software for my finance needs, I write the question that the software will answer. In one sentence and from the mouth of the person asking. In this case: Why can't I see what money came in and out of my bank account in my other programs? You would never look to buy a new bank program as the first answer to that question. Maybe an export.

You also know who should be in the room when testing this software out. If your bookkeeper is the one asking that question, have them test it out and the person that will be purchasing the software. Usually two different people in small companies.

My company had a similar question with our numbers a few years later: What am I paying for each month and why? There were answers in four different locations: our bank statements, our document storage program, our Microsoft account and our monthly report from our tax advisor. We had subscriptions to things we no longer used and software licenses for people who had left the company. All of these were correct programs to store that information. But the question wasn't answered in any one of them. Which led to the software I build today.

What are you paying for?

If you have that question written down, you can also look at the software you currently have. We had a piece of software that we paid for by user. For 2 years. We never had more than 6 users on it at any time. The vendor offered a cheaper option for this scenario. We never found out because no one asked. One call to the vendor would have solved that. No migration or training needed.

I would sit down with my current software once a year and do the same thing. If you can't answer a question with that software, call your vendor.

Use your own data

If you do decide that the software you're testing will solve your problem, test it with your data. A trial period will show you the software. It won't tell you if it will work with your data. Your account names and exports may not match what the vendor expects.

You'll spend more time the first week doing this. But that's the week you have the option to not buy the software.

When this won't work

This is my opinion from running my own company and helping others create software: There will be times that the program you have is the issue. Your vendor no longer supports the software or it doesn't meet your legal requirements. Writing down your question will help you figure that out too.

Some may say that you should have more than one question written down. I say have the question you know and let the other questions come.