That shiny new software demo looked amazing. The sales rep made it sound like it would solve every problem you’ve ever had. Your competitor just bought it. The pressure to pull the trigger is real.
But here’s what I’ve learned after watching businesses make technology decisions for over a decade: the companies that thrive aren’t the ones who buy the newest tools—they’re the ones who buy the right tools.
Before you sign that contract or enter your credit card, run your potential purchase through these five questions.
1. What specific problem does this solve?
“It will make us more efficient” is not a specific problem. Neither is “everyone else is using it” or “it’s the future.”
A specific problem sounds like: “We’re losing 3 hours per week manually transferring data between our CRM and our invoicing system” or “customers are abandoning carts because our checkout takes too many steps.”
If you can’t articulate the exact pain point this technology addresses, you’re shopping for solutions to problems you may not actually have. Write down the problem in one sentence before you evaluate anything.
2. What’s the total cost of ownership?
That $50/month subscription fee is just the beginning. Real costs include:
- Implementation time: How many hours will your team spend setting this up?
- Training: What’s the learning curve, and who’s going to teach everyone?
- Integration: Will it play nicely with your existing tools, or will you need additional software or custom work?
- Ongoing maintenance: Who handles updates, troubleshooting, and renewals?
- Switching costs: If this doesn’t work out, how painful is it to migrate away?
A “free” tool with a 40-hour setup process isn’t free. A $500/month platform that eliminates 20 hours of manual work might be a bargain.
3. Who will actually use this daily?
Here’s a pattern I see constantly: leadership gets excited about a new platform, purchases it, and then it sits unused because the people who were supposed to use it every day were never consulted.
Before buying, talk to the actual end users. Show them demos. Ask what would make their jobs easier. Their input isn’t just nice to have—it’s the difference between adoption and abandonment.
4. What does success look like in 90 days?
If you can’t define what “working” looks like, you won’t know if the technology is delivering value or just draining resources.
Set concrete benchmarks before you buy: “In 90 days, this tool should reduce our response time from 24 hours to 4 hours” or “We should be processing 50% more orders with the same staff.”
This also gives you a clear exit point. If you’re not hitting those benchmarks in three months, it’s time to reassess rather than hoping things improve.
5. What happens when something goes wrong?
Because something will go wrong. It always does.
Research the vendor’s support structure. Read reviews specifically about their customer service. Find out: Is support included or an add-on? What are their response times? Do they have documentation you can actually understand? Is there a user community for troubleshooting?
A powerful tool with terrible support becomes a liability the moment you hit a roadblock.
The bottom line
Technology should serve your business strategy—not the other way around. The goal isn’t to have the most tools or the newest platforms. It’s to have the right solutions that actually get used and deliver measurable results.
If running through these questions feels overwhelming, or if you’re facing a significant technology decision and want an objective perspective, that’s exactly the kind of strategic evaluation we help clients with at On Your Side Technologies. Sometimes having someone who isn’t emotionally invested in the outcome can save you from an expensive mistake.
The best technology purchase is often the one you decided not to make.
Want to talk it through? I keep a few virtual coffee spots open each month — grab one while they’re available → Book a virtual coffee
Photo by Jud Mackrill on Unsplash
