Software Selection

What Works

• Define the one problem you're buying the software to solve
• Try the free trial on your actual workflow — not a demo scenario
• Check integration with your existing stack (accounting, calendar, POS)
• Talk to one customer who isn't on their reference list

Watch Out For

• Annual contracts remove leverage after month 3 — negotiate monthly or quarterly first
• Feature count is a distraction — time-saved is the real metric
• Data portability: ask how you export everything before you sign

Frequently Asked Questions

How do I choose the right software for my business?

Start with the problem, not the features. Define what you're trying to fix, test the top 2–3 options on a real task, and pick the one your team will actually use.

Should I sign an annual software contract?

Only after running it for 30–60 days and confirming it solves the problem. Annual discounts average 15–20% but cost you leverage if the product disappoints.

What questions should I ask a software vendor?

Ask: How do I export my data? What's the uptime SLA? Who handles support — chat bot or human? What does the cancellation process look like?