While a good server admin or a good programmer with (relevant) generalist skills and people skills can succeed as a CTO, you need a CTO that knows your market and your goals and your organization and your customers, and that can quickly determine what works and what doesn't.

While a CTO is solving today's problems with today's shiny and with shiny duct tape, you also need a CTO that can identify and can hold both your short term and your broader and longer-term organizational goals in sharp focus. You need a CTO that establishes clear goals and measurements and trends, and a CTO that can then push, pull, poke, suggest, prod, cattle-prod or ego-stroke toward those organizational goals. And you need a CTO that adapts.

If a server admin or a programmer has the requisite adaptability and people skills and technology skills and presentation skills and has an indefatigable focus on making your market, hire him. Or her. But you're not selecting for and not hiring for server admin or programming skills here.

You want somebody with the technological skills of and the focus of the Borg.