Your organization is considering purchasing a new piece of software. You’ve looked at the product website. You’ve talked to the sales team. Everything looks great, but how can you be certain?

In this article, I’ll walk through the steps I take when choosing new software both for my own business and my clients. It takes some time, but it’s worth the effort.

Success Story

I’ve used the steps below for multiple clients. A big win was a church that wanted a new tool to track donations and publish a member directory. Not only did I find a cheaper, more user-friendly alternative to what they had been using, the new tool was able to replace a second, expensive piece of software.

By taking time to thoroughly review different options, this organization moved to a single tool that meet multiple use-cases and cut costs by over 40%.

How to Choose the Right Software

1. Identify the Main Use-Case

Whether you’re replacing an old tool or adding on something new, there is typically one overall need that this software must fill.

This could be “manage all of my donor contacts” or “automatically respond to customer emails”.

All other steps point back to this primary use-case that the software needs to meet.

2. List Main Feature and Functional Requirements

Create a short list of how you would like both admins and end users to interact with the software. These are your Feature Requirements.

A feature requirement could be “maintain separate newsletter lists for volunteers and donors” or “donors can choose from pre-set amounts or to set their own donation amount”. Focus on the hard requirements, not the preferred behavior.

Also create a list of how you would like the new software to interact with any existing tools that you use. These are your Technical Requirements.

A technical requirement could be “donor contact information syncs with my newsletter contact list” or “all attachments emailed by customers are uploaded to a Google Drive folder”.

3. Ask AI for Options that Meet Your Criteria

Go to your favorite AI chat and ask it for a list of software that meets your 1) main use-case, 2) primary feature requirements, and 3) any key technical requirements.

A few years ago I would have done this by Google search. Now AI search is the fastest, most effective way to get a short list of tools to review.

4. Check for Deal Breakers: Lack of Transparent Pricing, Free Trial, or Help Documentation

Transparent Pricing. If a software product doesn’t list a price, but only says to “Contact Sales for a quote”, I immediately cross the product off the list. Software that has unpredictable pricing either means that you’re expected to add custom development or that the company has poorly defined usage metrics.

Free Trial. If I can’t try out a product before I buy it, I’m not going to buy it. If you have to contact the sales to get access to a free trial, this is also a disqualifier because it probably means the software uses an old-fashioned deployment method. I only consider products that I can sign up for and test out immediately.

Help Documentation. Lack of high quality, self-service help documents are also an immediate deal breaker. If the company does not provide instructions on how to set up your product or how to resolve issues with the software, that means you’ll have to contact their customer support every time you need assistance. I want to use software that is user-friendly enough for me to resolve issues on my own.

5. Read 3-Star Reviews

I then head to Trust Pilot and read the 3 and 4-star reviews. I’m looking for patterns in the mildly negative feedback, such as “can’t export customer details”, “data doesn’t sync between lists”, “can’t create recurring events”, etc.

If a tool is basically good but has a couple of annoying limitations, I want to know about these in advance. I want to decide whether or not I can live with them.

(I read the 3-star reviews because I want to know what the difficult-to-please customers saw as feature gaps. The 5-star reviews almost always say they love the product and customer support is great, and the 1-star reviews almost always say the product doesn’t work and support is terrible. These are unreliable narrators.)

6. Test the Software

By this point I’ve usually narrowed the list down to 2-3 options, and it’s time to make use of my free trial. I recommend these steps:

1. Review the major screens and look for the features listed in your Functional Requirements.

2. Review the help documentation and look for articles that address your most important Technical Requirements as well as anything concerning that came up in the product reviews.

3. Test out the most important feature. Set up a ticketed event, create and publish a donation form; try out a real scenario that you would use the software for.

If a tool meets all the requirements but isn’t enjoyable or easy to use for a simple test, then you probably won’t enjoy using it in your day to day operations.

7. Choose the Best Option

After this assessment, I have a very good idea of the best option to meet the needs and budget of my clients. Yes, it takes some time to go through these steps. But this small investment can save costs and headaches that result from choosing the wrong software.

One Size Fits No One

Whenever someone asks what the best platform is, I always say the same thing “It depends”.

Your organization is unique. The way you operate might be similar to other organizations, but no two offices are identical. Why try to force your organization to fit into someone else’s shoes?

Get the right software that meets your needs. Make routine tasks easier for your staff and volunteers.

This will free up your time for the work you really care about.