The present application is generally directed to a method and system for coaching individuals such as, e.g., employees of organizations such as large enterprises, to achieve predefined goals through the preferably daily practice or use of preferably a single habit, skill, action, or behavior. For example, the method and system can be used to keep an individual focused and disciplined over time to change behavior such as, e.g, acquiring or reinforcing a new skill or habit. The system is preferably delivered through an automated, web-based application using, e.g., expert systems to simulate a live coach's response to different performance scenarios. The self-coaching method and system can strengthen an individual's focus, discipline, and perseverance over time and thereby dramatically increase the likelihood of success of achieving a reliable new habit or mastering a new skill. Briefly, the self-coaching method and system guides users through the process of articulating self-improvement or other goals and then helps them attain their personalized goals. Users can submit self-monitoring records preferably twice daily through the web-based application. These records help individuals focus on and renew their commitment to their plan of action, reflect on their experiences, and assess their own efforts. The web tool can provide users with graphic representations of performance measures, which are preferably updated daily. The system can simulate using, e.g., expert systems, a real coach's response to the user's problems and progress during the course of the use of the system, which can be, e.g., 21 days.