Good question. I don't know how much hands on ability a senior officer in any Military Intelligence role would need to have in the actual jobs of specialists under them. As officers I think they would have enough working knowledge to understand what the people under them are capable of, but not necessarily the same level of talent or specialization. They would think in terms of capabilities applied towards their mission. Units with this kind of mission are like special forces. They're hand selected, they have a lot of freedom of movement in how to achieve objectives and plan their own operations.

When you're talking about officers like Nakasone and Rogers though, its even harder to estimate these guys. What kind of officer would they put in place as the Director of the NSA? We're not talking just signals intelligence (hacking) there. The Director of the NSA basically leads an entire ghost army of research, intelligence, and operations capabilities. None of which you could open source the information to even estimate what that ghost army consists of accurately. I would say an NSA director would have the talent to know how to destroy (and so also defend) entire nations with weaponized information or lack of information and an NSA Director would have a good understanding of how to apply and withhold force (information/operations.)

Rogers' background started from cryptology. From there his entire career progressed in the direction of military intelligence. He was selected for transfer to cryptology in the 80s, but his career disappears for 20 years and re-emerges in Iraq with him being assigned to work with top brass (JCOS) as the HNIC officer specializing in computer network defense/vulnerabilities. (Basically, he set the objectives of any and all cyber/sigint work for the entire theater based on his own assessment of the information on the entire geopolitical landscape and potential threats relevant to and within Iraq.)

I would wager he was a very talented "hacker" himself.

If Rogers is on the Board of Advisors (he's the entire board of advisors) of 1 company, that company would have to be a pretty big deal for some reason. He's not there to troubleshoot their routers.