When consulting with SMBs, business owners almost always start by looking at what features a software product has. They should instead start by looking at what actual operational bottlenecks they have. Over my decade of consulting, I have seen countless organizations pay for enterprise-grade feature sets they will never use, all while missing the fundamental reliability they actually need to scale.

Software selection must be categorized as a strategic business decision, not a technical checklist. If the system does not align with how you plan to scale operations in three years, it is the wrong system, regardless of its current price or popularity. I advocate for "Deliberate Procurement" — choosing the minimum viable technical debt that allows for maximum business agility. Stop buying software for its features; start buying it for its outcomes.