Every week, a vendor promises a small business owner that their tool will save time, cut costs, and basically run the place. Some of them are right. A lot of them are not. After 30 years of watching businesses buy technology they never fully used, Dr. Melody White has a clear opinion: the problem is almost never the software itself. It is that nobody asked the right questions before signing up.
Here is what we actually walk clients through at On Your Side Technologies before they commit to anything new.
1. Who will own this day to day?
Name a specific person, not a role. If the answer is “whoever has time,” the tool will collect dust within 90 days. We see this constantly with CRM systems and project management platforms. The technology is fine. The ownership is missing. Before you buy, identify the actual human being who will be responsible for it.
2. What does it have to talk to?
New software rarely lives alone. It needs to connect to your accounting system, your email, your point of sale, your donor database, whatever is already running your business. Ask the vendor directly: what do you integrate with natively, and what requires a third-party connector like Zapier? Third-party connectors are not always bad, but they add cost, complexity, and one more thing that can break. Know what you are agreeing to before you sign.
3. What does the first 90 days actually look like?
Vendors will tell you implementation is easy. Push them for specifics. Who sets it up? Who trains your staff? Is there a dedicated contact or a help ticket queue? Dr. White recommends asking to speak with a current customer in a similar-sized organization, not a reference the vendor hand-picked. The onboarding experience is where most technology purchases either take root or fall apart.
4. What happens to your data if you leave?
This one almost never gets asked, and it should be non-negotiable. Can you export your data in a usable format? Who owns it? What is the process for canceling? Some platforms make leaving so painful that businesses stay out of inertia, not satisfaction. Read the terms of service on this point, or have someone read them for you.
5. Is this solving an actual problem or a perceived one?
Vendors are good at making you feel a pain you did not know you had. That is their job. Before you buy, write down the specific problem you are trying to solve and what “solved” looks like six months from now. If you cannot write it down clearly, you are not ready to buy. A purchase without a defined outcome is just an expense.
One thing you can do today
If you have software you are currently paying for but not fully using, make a list. Most small businesses are carrying two or three subscriptions that made sense at purchase and have since drifted into the background. That list is where your next technology conversation should start, not with whatever a vendor is pitching this month.
When clients come to us before a purchase rather than after, the outcomes are almost always better. We help you pressure-test the vendor claims, check the integrations, and make sure the tool fits how your business actually operates. If you are weighing something new and want a second opinion, that is exactly what we are here for.
Want to talk it through? We keep a few virtual coffee spots open each month — grab one while they’re available: Book a virtual coffee with Dr. White
Photo by Anthony Riera on Unsplash
