This chapter draws upon the organizational learning literature to define and describe key elements of intelligent failure and clarify the distinction between failure and intelligent failure. We highlight how some organizations have attempted to recognize and reward thoughtful failure, and we explore the processes and outcomes of these efforts. Research suggests that recognizing and rewarding intelligent failure can positively influence organizational outcomes including greater tolerance for risk-taking, enhanced individual creativity, and increased organizational effectiveness. The benefits of intelligent failure can be further enhanced if organizations build a “spirituality of imperfection” into their cultures. A spirituality of imperfection sees imperfection and mistakes not as limitations but as an inherent part of our humanness. Organizational leaders who build cultures that draw upon a spirituality of imperfection allow employees to seek help and stop “the blame game” and, in so doing, provide a surer pathway toward greater individual development and increased organizational effectiveness. We close the chapter with suggestions for developing organizational cultures that encourage intelligent failure.