How? Be involved on technology listservs. Read the "tech" sections of library publications. Read some good library technology weblogs or online publications. That's where the good ideas have been coming form as of late. Administrators don't have to know every little thing about technology, but at least (pleeeeeease) be familiar with it and discuss it with your staff. If you don't, you are turning a blind eye to a huge area of librarianship. And your staff will know. Believe me.
Sarah also states that admin do not have to live and breathe tech but they should be able to carry on a conversation about trends and practices. I have met with a lot of librarians and more than once has someone taken me aside and said "How do I get my (director, boss, supervisor) to get this stuff?" That's the nice way of putting it. The other side, as I pointed out and Sarah agreed, are the librarians who joke about adminstrator X at the water cooler and the fact that he or she "can't even open an attachment in e-mail" It happens, as LIB wrote... "believe me."