An Indiana man was mistakenly released from prison on Friday after a court hearing. Cook County Sheriff Tom Dart says that an antiquated system allowed the prisoner to slip through the cracks. Dart says a literal paper trail follows the process of transferring inmates. Is the County operating with out of date systems that could create more errors like this? Sheriff Dart and Cook County Treasurer Maria Pappas offer details about how their offices operate, and what could be improved. Dylan Richard, former Director for Engineering for Obama for America and tech architect, explains what strategies work best to get many parts working as a whole when targeting the same mission.