I think one of the issues you run into with this question is that the higher one moves up the chain, the more generalized the skill-sets need to be.

Or perhaps that is an inaccurate statement.

I think that a more accurate statement would the higher one moves up the chain, the broader the skill sets need to be and as a consequence of that broadening, the shallower the specialized skill sets become. A subtle but important difference.

As someone who is at the level immediately below the CIO, in an enterprise that is transitioning from a regional operating model to a global one, I find that I am performing many of the duties of a traditional CIO; while the true CIO is very much a strategic operations leader, with far more experience in overall business operations than in “hard” Information Technology. Does that make him/her a better CIO? For the role that they are playing within the company, I believe the answer is yes.

But would they be a good programmer or systems administrator being 20 years removed from the nuts and bolts I.T.?

Would I?

I’m much closer to my origins in my I.T. career, and am in a position where I’m already finding myself farther removed from that hands-on kind of I.T. that moved me up the ladder in the first place. Yet I find myself looking at some of these posts for CIO openings and many seem far more focused on whether someone can code for SQL or set up a Redhat Server than whether they can decide on the technologies that will make their enterprise more competitive. This is the fault of the enterprise that is searching for a CIO, less a fault of the individual looking to rise to that level.

As for the answer of what someone looking to rise up to a CIO level should be striving for in skill-sets I think that ultimately it depends on what kind of company you wish to work for. I can only speak for myself in that the occasional inquiries and poaching attempts are more frequently for someone who is more strategic in view, with a broader, shallower skill-set in more traditional I.T. disciplines. But these inquiries generally involve positions in larger enterprises than in smaller ones. I think smaller and more traditional operations are still looking for a CIO that can write C# in their sleep or replace a RAID controller at 3:00am.

Or as many posts have pointed out here @ CIO, the CIO position is most certainly in a state of transition.