With the due date for the reauthorization of No Child Left Behind (NCLB) right around the corner, "Education Next" thought it apt to probe the lessons learned in the five years since the act's passage. This article presents an e-mail interview with Sandy Kress, a lawyer and former school board member who, as a domestic policy advisor in the White House, served as President Bush's chief negotiator during the original NCLB debate. In this interview, Kress was asked about the genesis of key aspects of the federal law, whether its crafters foresaw any of its major glitches, and what he thinks of NCLB's prospects going forward. (Contains 2 figures.)