As Head of IT at Frogslayer, I’ve seen firsthand how the right digital tools can transform efficiency, sales, and growth. Research consistently shows that companies achieving success in digital transformation see measurable gains, including higher valuation and improved performance across the board.
But here’s the challenge: most companies still struggle to get it right. From small businesses to Fortune 500 firms, only a minority successfully align software decisions with their long-term goals.
If you’ve already explored our Build vs. Buy Analysis and decided that purchasing off-the-shelf software is the best path forward, this guide is designed to help. Even with the right decision in hand, navigating the complexities of software procurement requires a structured, thoughtful approach.
In this blog, I’ll share Frogslayer’s method for evaluating and purchasing software. From identifying requirements to negotiating pricing, we’ll walk through a step-by-step process to ensure your software choices support your business goals now and in the future.
Resources for Clients
Custom vs Off-the-Shelf Software: Frogslayer’s Build vs Buy Analysis
Read postWhy Software Decisions Should Be Team-Driven
If you’re in IT, you likely thrive on solving problems—I know I do. But one of the biggest lessons I’ve learned is that software decisions are best made collaboratively, not from the top down.
Recent research confirms that team-driven decision-making consistently delivers better outcomes. When teams are empowered to explore options and contribute insights, you don’t just make better decisions—you foster engagement and encourage early adoption.
Let Your Team Test Drive Tools
Empower your teams to experiment with products or subscriptions early in the process. This exploratory phase often uncovers critical requirements that IT might not identify alone. By the time IT steps in, teams typically have a clearer understanding of their needs and can flag must-have features.
This proactive approach speeds up the process and ensures that selected tools align with both operational needs and strategic goals.
The Ultimate Guide to Evaluating and Buying Software
Establish a Process
Prior to your search, you need to know what you are looking for. If you’re already following a process that you want the software to automate, start by documenting it. This can be as simple as a checklist or something more complex.
Next, start using simple tools like Word, Excel, or Notion to track and manage your process. These tools not only help you stay organized but also refine your understanding of what you need a software solution to accomplish. By laying this groundwork, you’ll have a clearer picture of the capabilities you’re looking for in a new tool.
Pinpoint Critical Requirements
Once you have a process in place, it’s time to define what you need the software to do. This might include:
- Client order tracking
- Online portals for customer access
- Live chat capabilities
- Reporting
- Document Management
- Enabling AI Capabilities
…list could go on and on forever. Especially since there’s likely an off-the-shelf solution for every aspect of work.
As you brainstorm requirements, group them into must-have and nice-to-have categories. This prioritization will make it easier to evaluate potential solutions and focus on what matters most to your organization.
Expand Your Search for the Best Fit
Begin researching software options online. For common business needs, a simple search can yield a wealth of results. Try searching for “alternatives to [major player]” to discover comparison sites and reviews.
For niche requirements, you may need to dig deeper by exploring online forums or asking peers in your industry for recommendations. If integration with existing systems is critical, check whether potential software solutions offer compatible integrations to avoid unnecessary headaches later.
Compare Options Effectively
Start by building a spreadsheet to organize and evaluate the available options. One effective method is to create a summary page with the software options listed on the left and key features across the top. Use marks or comments to indicate how well each solution meets your criteria. We have our own model that’s been used and tested time and time again.
You can download a copy of our template for free at the end of this post.
Gather initial information online to start populating your spreadsheet. Once you’ve narrowed down your list, schedule demo calls with your top choices. For each demo, create a dedicated tab in your spreadsheet where you can take notes and paste in screenshots.
During these demos, ask detailed questions—especially “what-if” scenarios like, “Could it handle this?” or “How would it integrate with our current tools?” These discussions often reveal additional features or needs you hadn’t considered. Update your spreadsheet as you go, adding new items to your requirements matrix to ensure a comprehensive evaluation.
Try It Out
Whenever possible, take advantage of free trials to test the software in your real-world environment. Trials provide invaluable insights into how well a solution meets your needs.
For example, in some cases, users might find that integrations are non-existent, too complicated, or require other subscriptions.
If trials aren’t available, consider requesting a second demo call to dive deeper into your top options. Alternatively, pay for a one-month subscription to fully evaluate the software before committing to a long-term agreement.
Make Your Decision and Negotiate Pricing
After trying out several options, consolidate the most pertinent information into your summary spreadsheet. Use this to compare your top choices side by side, weighing costs against value, features, and functionality.
Once you’ve identified your preferred solution, leverage your research to negotiate pricing. Highlight competitor offerings to secure a better deal from your chosen vendor.
Don’t Rush the Decision
If none of the options feel like the right fit, don’t rush to make a purchase just to fill the gap. Based on your research, there may be promising tools still in development or features in the pipeline that better align with your needs.
If you find a vendor working on a required feature, request a discount or a written agreement guaranteeing future updates. This ensures their promises align with your expectations and protects you if the feature isn’t delivered as promised.
Save Your Research
Your research is an invaluable resource—don’t let it go to waste. Save it for future reference, whether to justify your decision to stakeholders or to simplify the process of finding a replacement if the chosen software doesn’t work out.
Comprehensive documentation also comes in handy when explaining to team members or leadership why one solution was selected over another. It saves time, builds transparency, and helps streamline future software evaluations.
Treat Software as a Journey, Not a Destination
By following this structured approach, you can simplify the complexities of software procurement and ensure your decisions are informed, strategic, and aligned with your business goals. Whether you’re choosing software to meet immediate needs or support long-term growth, these steps will set you up for success.
Drive Transformation with the Right Tools
Buying software isn’t just about solving today’s problems—it’s a strategic investment that shapes your future. By empowering your team, aligning your process, and taking a long-term view, you can turn software decisions into a competitive advantage.
To make the process even easier, we’ve created a downloadable Software Comparison Template to help you evaluate and compare your options side-by-side. This tool is designed to simplify your decision-making and ensure you choose the solution that best fits your business needs.
Done right, your software choices will fuel growth, efficiency, and innovation across your organization. If you ever need help evaluating the best digital solution for your business, our team is always happy to help.
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Brian Cahill
