The U.S. Department of Justice, Bureau of Justice Assistance funded the International Association of Chiefs of Police (IACP) initiative for smaller police agencies to develop and coordinate a mentoring project for new police chiefs serving communities of 25,000 or less residents. The project’s intent is to support the professional development of new police chiefs by providing an experienced police chief as a mentor. The pair works together on the issues identified by the new chief as the most essential. The program provides new chiefs with someone to call when they need advice, support, or guidance from someone with more experience. The article presents selected personal experiences about mentoring programs that have assisted police executives and their agencies. These examples show personal assistance received from executive mentoring and mentoring programs for the entire department and include: the Knoxville Police Department, IA; the Fairfax County Police Department, VA; the Lafayette Police Department, CO; the Fairfax County Sheriff’s Office, VA; and the Minnesota Chiefs of Police Association, MN.