The most expensive technology mistake I see in small business isn't a bad vendor or a botched implementation. It's having no one in the room who actually understands both sides, the technology and the business.
For many owners, IT is an area they don't feel comfortable with or fully understand. So they do what they always do when that happens. They hire for it. Outsource to an MSP or hire internally, and both can be perfectly competent at what they do. Neither is structurally positioned to ask whether what they're doing actually serves the business.
One has a financial interest in what they recommend. The other knows how to build and fix, but rarely how to evaluate whether something should be built at all. And the owner has no real way to know what's truly working. They only know what they see, not what's under the hood, where the risk lives.
That's not a technology problem. It's an accountability problem.
This is where someone who speaks both languages comes in. Someone who asks the right questions, takes the time to understand the business goals, and works with IT to align to them. It creates real accountability for a critical function, someone whose only interest is whether technology is working for the business and not the other way around.
Accountability without understanding isn't accountability. It's hope.