This chapter addresses the factors that shape whether it is in the employer's interest to make i-deals as opposed to relying on more standard arrangements. The chapter begins with two cases illustrating how organizational factors impact i-deals' effective use. Standardized resources provide employers a means for signalling their quality as an employer and for future opportunities, and are particularly important when productivity depends on cooperation among workers. I-deals pose a dilemma for both managers and Human resource professionals. HR strategies account for variations in employer use of standardized, position-based, and idiosyncratic arrangements. To illustrate how HR practices and strategy, managerial action, and organizational culture impact the use and sustainability of i-deals. The functionality Feather River Science Systems' (FRSS) i-deals from the firm's perspective and the lack of it at Lakeside Leadership Institute (LLI) resulted from differences in the way the two firms stacked up on key organizational features.