There's a lot of things out there to keep up with. Fashion trends change every season, that new Netflix series that "everyone" is talking about, the latest new smart phone, fun new apps - the list never ends.
While it's not that important for you to keep up with the new "mom jeans" trend, what IS important is that your technology keeps up with both internal and external changes.
Your organization is continually evolving, taking on new employees, new programs, new grants and funding sources. Then add on top of that external influences such as regulatory changes, new reporting requirements, and increased demand for your services. Your Finance, HR, Payroll and Case Management systems may be perfectly suited to your organization at the Go-Live date, but within a year, or even a few months things may be out of date.