This article explores the common problems associated with ineffective diversity initiatives and what steps a firm can take to cultivate a successful plan. Diversity dilemmas in the workplace have long frustrated advocates who desire not only to see greater representation of minorities and women in firms, but also that those people are integrated across the firm and accepted as valued, productive members, of the firm’s culture. Knowing how an initiative fails to achieve diversity goals and learning from successful examples will enable firms to create a better work environment, capitalize on market opportunities, and enjoy many other benefits.