ON THE FIRST Monday of the 2003-04 school year, Pablo Sierra was not where he hoped to be. Instead of greeting students as the new principal of a Chicago public school, Sierra was driving downtown for another round of meetings with district officials, trying to keep his spirits up and hoping that a position would open soon. As a newly minted graduate of the widely heralded New Leaders for New Schools training program for aspiring principals, Sierra (and the developers of New Leaders) had understandably expected to find a slew of opportunities awaiting him. He thought that his prestigious MBA, private-sector experience, and nine years as a classroom teacher would distinguish him from more traditional applicants for the principalship. The intense yearlong "residency" program developed by New Leaders would make up for his lack of traditional administrative experience.