4 Questions Before You Buy That Next Software
A Goldman Sachs survey found that 88% of small businesses want to use AI — but 45% don't know where to start. The problem isn't knowledge. It's that most technology is built for boardroom pitch decks, not for the operator running payroll on Friday and fixing a scheduling disaster on Saturday.
Last year I sat across from a franchise operator running 88 locations. Smart guy. Knows his numbers cold. Runs his DoorDash error rates down to the hundredth of a percent.
He manually downloads reports from six different platforms every week. Copies numbers into a spreadsheet. One store at a time. Eighty-eight times.
When I asked why he doesn't use one of the dozen AI tools designed to do exactly this, he didn't blink.
"They all want $199 a month per location."
Do the math. That's $17,500 a month. Over $200,000 a year. For a reporting tool.
He has stores doing $50 a month in error charges. You think he's paying $199 to recover $50? He's not stupid. He's stuck in a market that hasn't figured out how to price for real businesses yet.
And he's not alone. Another 47% of small business owners say it's too hard to pick the right tools. Not because they're unsophisticated. Because the tools aren't built for them.
So before you sign that next contract, open that next free trial, or hand your credit card to a vendor who swears their platform will "change everything" — run it through these questions first.
Who Owns the Data — You or Them?
If you can't export your customer data, transaction history, and reports when you leave a platform, you don't own your business data — they do.
This one should scare you more than it does.
I watched a franchise operator spend weeks negotiating with DoorDash about who owns his own transaction data. DoorDash's argument? "That data wouldn't exist without our platform."
His argument? "Nobody goes on DoorDash to discover McDonald's. They already know what they want. You're just the delivery method."
He's right. And this fight is everywhere.
Google recently started charging a 5% commission every time someone clicks "Order Online" from a Google Business listing — even when the customer searched for the restaurant by name. The restaurant had to send a cease and desist letter just to get their own direct ordering link ranked above DoorDash's.
That's not a partnership. That's a tollbooth on your own customers.
Before you buy anything, ask the vendor directly: If I leave this platform in a year, what happens to my customer data? My transaction history? My reports? Can I export everything, or am I locked in?
If the answer is vague, walk away. Your data is your business. Full stop.
If you rely on reporting or customer data to make decisions, start asking questions about ownership before you sign. Understand what the vendor owns and what they'll share. You don't want to buy something that locks you into their ecosystem with no exit ramp.
Run the Math on Your Worst Month, Not Your Best
Here's where most operators get burned: they evaluate a tool based on their best month or their busiest season. That's like buying a truck because it handles great on flat highway, then wondering why it struggles on the mountain roads you actually drive every day.
That franchise operator I mentioned? He told me about a tool called Loop AI. Loved the product. Thought it was brilliant. But at $199 per month, the math only worked during high-volume months when his stores were pulling in $1,000 to $1,500 in error charges.
His slowest location in Nephi, Utah? Fifty bucks a month in errors. You're paying $199 to save $50. That's not ROI. That's a donation.
The same logic applies even if you only have one location. Your business has high months and low months. Busy seasons and dead zones. If a tool's flat fee only makes sense during your peak, you're subsidizing it during every slow stretch.
So when you're evaluating any tool, whether it's for delivery errors, scheduling, inventory, whatever, don't run the numbers on your best month. Run them on January. Run them on the week after a holiday when traffic drops off a cliff. Run them on the scenario where you're barely breaking even.
If the ROI doesn't hold up when things are tight, either negotiate a different pricing structure or keep looking. The right tool should earn its keep in every season — not just when business is already good.
Are You Fixing the Right Problem — or Just Automating the Wrong One?
Most operators buy software to solve a symptom when the real constraint is buried one or two layers deeper — and no tool can fix a problem you haven't correctly diagnosed.
I talked to a gym owner who wanted to add more programs because membership growth had stalled. More class types. More options. More complexity.
He couldn't answer a single one of these questions:
Which trial pass converts to membership at the highest rate?
What behavior in the first 30 days predicts retention?
What's his actual cost to acquire a member?
When we pulled his data, we found that members who didn't hit ten visits in their first 60 days had a 61% churn rate. He didn't need more programs. He needed a tighter onboarding system to get people through the door ten times.
Different problem. Different solution. Way less expensive.
Here's another one. A $60 million digital grocery company wanted "AI-powered personalization" for their app. Ninety-nine percent of members had downloaded it. Only 30% ever used it to shop. The problem wasn't personalization. It was figuring out why 70% of people who had the app on their phone refused to open it.
AI personalization would have just made a bad experience slightly more customized. Like putting a fresh coat of paint on a house with a cracked foundation. Waste of money.
Before you buy anything: Can you clearly articulate the problem you're solving? Not "we need better data" or "we need to be more efficient." What specific problem is costing you time, money, or customers right now?
If you can't answer that in one sentence, you're not ready to buy software. You're ready for a diagnostic.
Can You See ROI Within 90 Days — or Is This a "Long-Term Investment"?
If a vendor can't show you a realistic path to return within one quarter, proceed with extreme caution — especially if you're a small operator watching every dollar.
Here's my rule. If a vendor can't show you a realistic path to ROI within one quarter, be very cautious.
I'm not saying every tool pays for itself in week one. But if someone tells you "this is a 12-month play" and you're a small operator watching every dollar? That's a red flag. That's a vendor telling you to be patient while they collect your subscription fees.
One of my clients — a wine shop — spent three months building what most people would call boring infrastructure. Tracking systems. Automated follow-ups. Connecting sales to marketing activities. Nothing glamorous. Nothing that would make a LinkedIn post go viral.
Now she can see which events drive repeat purchases, knows her customer acquisition cost, and watches automations convert attendees into buyers in real time. She didn't need a $500-a-month AI tool. She needed to connect the dots between what she was already doing.
The ROI showed up in weeks, not years. Because the system was built around her actual constraint, not a vendor's feature list.
If you are swapping one system for another, you should expect to see return within one quarter. Make sure that's possible before you sign.
Two Bonus Questions Worth Asking
Will Your Team Actually Use It?
I once worked with a franchise executive who supports 54 boba tea locations. He was spending every Sunday manually pulling numbers from Toast, store by store, plugging them into Excel. His wife was losing her mind.
He knows a CSV download exists. He knows there are tools that could help. But here's what he told me: "I can download it, but then how do I get it into the format I need?"
This is the gap nobody talks about. The tool exists. The feature exists. But the workflow between the tool and how you actually use the information? That's where it falls apart.
Before you buy, ask yourself: Will my team use this on a Tuesday afternoon when they're slammed? Or only during the training session when everyone's paying attention?
The best technology disappears into the workflow. If it adds a step, adds a login, adds a tab — it's dead on arrival. Your people are busy. They're not going to change their behavior for your software. The software has to change for them.
2. Can You Build It Yourself First?
Here's the part that gets me fired up.
One of the coolest things happening in technology right now is that it's giving the power back to small operators. Software bloat? Big costs? No worries. You can work around it. Build your own micro-tools. Do what makes sense exactly for your workflows.
The tools that used to require data engineers and six-figure budgets? They're accessible now. A boutique gym can track member behavior, automate engagement sequences, and identify churn risk. A fly shop can set up inventory alerts and automated email sequences to their existing customer base. A franchise operator can build a blended error rate report across six platforms without hiring a consultant.
Not all of it requires AI. Some of it is just connecting systems that already exist. Some of it is a well-designed spreadsheet. Some of it is a $50-a-month automation tool that does exactly the one thing you need.
Before you buy the $300-a-month all-in-one platform, ask: Can I solve 80% of this problem with what I already have?
You'd be surprised how often the answer is yes.
The Bottom Line
I'm not anti-technology. I build systems and technology products for a living.
But I've also watched too many operators buy the shiny thing because a sales rep made them feel behind. And then six months later, nobody's using it, the data is locked in someone else's platform, and they're back to the spreadsheet.
Your business doesn't need more software. It needs the right software — priced for your reality, solving your actual constraint, adopted by your actual team.
Ask the questions first. Then buy.
Frequently Asked Questions
How do I know if my business actually needs new software?
Start by identifying the specific problem costing you time, money, or customers right now. If you can't name the problem in one sentence, you likely need a diagnostic before you need a tool.
What's the biggest mistake small businesses make when buying technology?
Buying software that automates the wrong process. The tool works perfectly — but it's solving a symptom, not the root constraint. That's how operators end up with five subscriptions and the same problems.
Should small businesses use AI tools in 2025?
Yes — but strategically. AI is a force multiplier when applied to a clearly defined constraint. It's a money pit when applied to a vaguely understood problem. Start with the problem. Then evaluate whether AI is the right solution.
How do I evaluate software pricing for a multi-location business?
Run the ROI calculation on your lowest-performing location and your slowest month — not your best. If the math doesn't work across your entire operation, either negotiate usage-based pricing or keep looking.
What should I do before investing in any new business tool?
Ask four questions: Who owns the data? Does the pricing work for all my locations? Am I solving the right problem? Can I see ROI within 90 days? If any answer is unclear, pause and get clarity first.