The Supreme Court is a place where this is particularly noticeable, because there are only 9 justices. But honestly, the median age of all politicians is probably too high to be making any sort of policy with regards to technology.
Law gets thorny though because of precedent. Even now, the majority of legal precedent for computer crimes is based on cases that were from a time prior to the personal computer existing. One of the reasons privacy gets so weird and heated is because many if not most of the major cases cited in court decisions are about telephones as the most advanced representative technology. My bet is that at least one telegraph case still gets cited every once in a while.
This may be unavoidable, but the article makes a solid point that it takes people who are comfortable with technology to make sensible rulings, even if the precedent is sparse at best and bizarre at worst.