A few signs tend to show up in the same order.
First, reporting starts taking longer, not shorter, even as staff gets better at their jobs. Then, the same information gets entered into more than one system, and eventually those systems stop agreeing. Finally, leadership starts making decisions from a gut sense of the business rather than a report they trust.
None of these are technology failures on their own. They're signs that the way information moves through the organization hasn't kept pace with how much the organization has grown.