Today's technology-based society and the vast influx of new information make leadership development a necessity. Many of the world's finest and most successful leaders have trusted mentors. Mentoring has emerged as a means to cultivate the leadership skills of current and future leaders. Mentoring has a rich history and harbors immense learning potential, which is supported by the theories and concepts of prominent researchers and philosophers such as Vygotsky, Rogoff, and Bruner. Mentors take on various roles and, like chameleons, transform their roles to fit the needs of their mentees, including becoming coaches, supporters, counselors, educators, and sponsors. The benefits of both mentors and mentees are extensive, ranging from increased self-esteem, awareness, insight, and professional skills to reduction of stress. While the benefits to mentoring are immense, personal and societal constraints such as time, incompatibility, and inadequate training show that engaging in mentoring takes immense time, effort, and commitment in order to obtain the desired results.