Survey Reveals Vast Differences in How Successful and Regretful Buyers Navigate Software Purchases
According to Capterra’s recently released 2025 Tech Trends Report, 59% of global businesses regret at least one software purchase made in the last 18 months, with a majority of the regretful buyers describing the financial impact as “significant” or “monumental.” How businesses construct their vendor lists plays a critical role in the success of their software purchases.
“At this initial stage, it is also highly recommended to clearly identify the goals and desired outcomes of the software”
This year’s report closely examines the three stages that businesses tend to follow during the software buying process and where things often go wrong when they compile and evaluate vendors. Capterra’s global survey of over 3,500 businesses provides guidance on how to build a solid vendor list, based on the researched actions of successful buyers:
Stage 1 – Compile a strong initial list with a clear north star
As soon as the decision is made to purchase software, buyers will immediately make an initial informal list of potential options in their head. Even though buyers are far from making a purchase at this point, they can still make mistakes that send them down a bad path.
For example, research indicates that placing the responsibility of evaluating a potential software purchase on one person, even at a small business, is not the best practice. Sixty percent of regretful software buyers are sole decision-makers in purchase decisions, compared to 48% of successful software buyers. Notably, successful buyers most often form a purchase group consisting of people from various departments, such as IT specialists, purchase stakeholders, and prospective users. This ensures all perspectives are taken into consideration as options are evaluated.
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“At this initial stage, it is also highly recommended to clearly identify the goals and desired outcomes of the software,” adds Brian Westfall, principal analyst at Capterra. “Businesses that have a clear goal in mind have more success than those that simply buy software to upgrade or to stay ahead of the competition. Identifying the goals and outcomes at the beginning effectively serves as a ‘north star’ for the team as it evaluates different options.”
As the team identifies potential products, the findings show it is important to build an initial list based on vendor reputation and product experience. In fact, successful buyers are 50% more likely to factor in previous experience with the product or vendor when putting together their initial lists, while regretful buyers tend to cite social media, advertisements, and media coverage as their information sources. So, if members of the purchasing group have prior experience with the product or know which vendors have a good reputation, that is valuable insight to consider.
Stage 2 – Build a formal shortlist based on objective sources and expert recommendations
With the initial informal list compiled – typically consisting of four or five products – now is the time to conduct formal research.
“While it can be tempting to stick with the initial list, the survey found that it is advantageous to remain flexible as successful buyers are much more open to revising their initial list to include a vendor they had not initially considered,” says Westfall.
During this stage, businesses rely on research to pare down their options into a shortlist. However, not all third-party sources are created equal. Research indicates the most beneficial insights are gathered from sources such as recommendations from industry experts, product comparison sites, and verified reviews. Successful buyers are at least 50% more likely to factor product comparison sites and expert recommendations when doing research to create their shortlist.
Large language models (LLMs), such as ChatGPT, have emerged as popular tools for conducting research, but businesses should proceed with caution. Regretful buyers are 68% more likely to factor information produced by ChatGPT to develop a shortlist.
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After doing research, successful buyers average nearly one whole less product on their shortlist (3.0) than regretful buyers (3.9)–indicating a willingness to cut options that don’t truly fit their needs and goals.
Stage 3 – Test drive the top products by taking advantage of demos and trials
After completing their research, successful buyers are more likely to engage all the vendors on their shortlist. While it may be easy to engage with only one or two vendors on the shortlist for efficiency’s sake, taking the extra time to connect with more vendors pays off in the long run.
In addition to discussing product details with vendors, businesses should seek out product demos and free trials to see how the software would work specifically for their business. This can help with evaluating user-friendliness, whether the software is compatible with existing systems, the level of training that will be required, and the level of tech support provided.
It is also imperative to have a firm grasp on the full cost of software ownership before making the final decision, especially understanding any unexpected costs that didn’t come up in initial discussions with the vendor. The top product-related reason why businesses regret a software purchase is because the investment cost more than they expected.
As businesses prepare to make a decision, timing is also a key indicator of a successful purchase. Most successful buyers (57%) take three months or less to evaluate software options, while most regretful buyers (54%) take five months or more. While careful evaluation is important for any software purchase, research shows that delaying a purchase due to indecision does more harm than good.
Capterra’s report reveals that 75% of organizations plan to spend more on software in 2025, meaning it’s vital that businesses rethink how they build vendor lists to find the best software for their specific needs.
