The theme for the CIO 100 Awards changes each year to reflect what we believe to be most compelling and important for business. In recent years, we\u2019ve selected integration, resourcefulness and agility. This year, we decided that the time was right to honor boldness.Boldness, as we define it, is the willingness to embrace significant risk for the sake of great reward. Organizations that are bold are playing to win, not just to survive.Last fall, we developed an online application that asked organizations to identify their endeavors that aimed for a great prize\u2014be it revenue generation, business transformation or competitive advantage\u2014and assumed significant risk, with a plan to mitigate it. We then solicited applications through advertising, newsletters and e-mail. As the applications rolled in, our staff nominated additional organizations that we thought met our bold criteria, and we invited those nominees to apply as well. Teams of CIO editors and writers then read through the applications and made recommendations. We asked ourselves whether the prize the organization was aiming for was great enough, whether the investment was large enough, whether the risk was significant enough, and whether the mitigation plan was smart enough. We compared one nominee to another. Inevitably, some nominees rose; others fell.Eventually, we arrived at the magic 100. And because we believe that boldness is something that can be learned, we offer these 100 honorees as exemplars.