How to Know If New Software Will Really Give You a Return

Do you constantly get sucked into a rabbit hole exploring a new product you think will be the magic pixie dust for your pain? Same. There are about a zillion tools out there that claim to solve the exact problem you have, and somehow half of them either don't work in your context or make you choke on your coffee when you finally see the price tag.

I've been on both sides of this. As an IT consultant I'm supposed to know what's out there. As a business owner, I'm as much a sucker for a good pitch as the next person. Here's how I make myself slow down before I click the "start free trial" button.

Get clear on what you actually need before you type a word in the search bar

A good salesperson will put words in your mouth. A great landing page can do the same thing. So you need to know what you're looking for before you go looking.

Start with the problem, not the pain point. These are different. The pain point is "I hate that I can't check inventory from my phone." The problem is "I need to see inventory from a mobile device when I'm at the supplier." Write it in one sentence.

Then get your requirements down:

• Functional requirements. What does the tool actually have to do? For our example: the user must be able to access inventory information on a mobile device.
• Non-functional requirements. What has to be true for the tool to work in your context? Performance, security, usability. In our example: the interface must work on iPhones.

In simpler terms — what does it do for you that you NEED and WANT, and what has to be true for it to actually work in your setup?

Then set a budget by asking four questions:

1. What cost am I replacing?
2. What's the time and cost to fix what I already have — and what's the expected return?
3. What is it worth to make this pain go away?
4. What revenue does this actually unlock?

That whole exercise is what people call a business case. It's also a great thing to hand off if you want someone on your team to do the research for you.

Watch for signs it's not really for a "small" business

Some tools are dressed up for small business marketing but priced and configured for enterprise.

Be wary when you see:

• No pricing published on the site.
• Reviews that mention ongoing "maintenance" costs.
• Use cases that don't look like yours.

Look for:

• Use cases specific to your industry and company size.
• The ability to add features as you grow without a full migration.
• Modular, flexible pricing so you can start small.
• Real customer service and training resources for teams without dedicated IT.

Watch for signs the product isn't actually that great

Be wary when you see:

• It isn't on any credible top lists or review services.
• Tons of reviews with no actual testimonials — just generic "great tool!" one-liners.
• A price that's dramatically lower than everyone else's, with review complaints about training, documentation, or customer service.

Look for:

• Reviews with both pros and cons that get specific. Search for your own pain points inside them.
• Detailed demo and walkthrough videos on YouTube from real users.

Watch for signs it'll take more skill or time than you have

Be wary when you see:

• The vendor offers "professional services" to set it up.
• A cottage industry of Fiverr sellers configuring it.
• Reviews that mention pain around configuration, setup, or integrations.
• Public help pages that look extremely complex — references to scripts or code you can't read.

Look for:

• Long free trial periods.
• Your current integrations listed as supported.
• YouTube walkthroughs of configuration.
• Searches like "how hard is it to switch to ___" returning honest answers.
• Clear, plain-English documentation.

Watch for signs you'll need other software to make it work

Be wary when you see:

• Testimonials and use cases that keep name-dropping other tools you don't own.
• Tutorials titled "X with Y" — where Y is the tool you'd have to buy separately.

That's a signal the product only really shines inside a bigger stack.

The discernment question

Before you click that "sign up" button, ask: can I explain, in one sentence, the problem this solves — and can I name the return I expect on my money and my time?

If you can't, close the tab and go back to your notes. A tool you can articulate is a tool you can actually get value from. A tool you can't is going to become another monthly subscription you keep meaning to cancel.

Here's an assignment for the week: make a list of every piece of software you use and note where each one connects to another. It's a small project, and it saves an enormous amount of time the next time you're tempted by a shiny new thing.

Prefer to listen? Find the episode here.