That's absolutely an issue. Some get in a job, get comfortable, and refuse to change.
In radio systems, that's kind of difficult to do, or those that do it don't last long. Technology changes, and you have to keep up. FCC mandated narrow banding required a lot of radio systems to be updated/changed/reprogrammed, so that sort of prevented a bit of stagnation. Some rely on contractors or vendors for everything, so it does happen.
In a somewhat related story, I know of several companies that boast about how long employees stay. While that can certainly be a good thing, it can also be a hindrance, if folks settle into the mantra "we have always done it this way." It somewhat relates to radios, in that folks who have done this for a long time tend to believe they have a firm understanding of the concepts, because that's how it worked a long time ago or they assume based on incorrect fundamental knowledge.
I think employee longevity is more of a good thing than a hindrance. I retired from a government agency with 31 radio sites and hundreds of non-radio sites, 5 years ago, I was on the maintenance side. I can say that the morale is higher, lots of comradery, people are motivated, eager to learn new technologies, create new test procedures, miraculously maintain documentation, etc. Some people are like an encyclopedia, ask them a question about a site and they will tell you all about the power plants, type of systems, traffic on the systems, etc so the continuity of info is greater. During an emergency such as a site or microwave hop down, we can count on them any hour of the day to reroute T1 circuits. When the PD or FD calls for a command post, we'll be right on top of it building T1 circuits to the CP, providing Intranet, video, & dial tone.
With a large organization that I was in with lots of different types of technician positions such as in radio, data, telephone, system monitor, FD & PD dispatch centers, mobile installs, cable crew, intrusion alarms, etc. Everyone's skill set is matched with the position.
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