At its core, impact investing promises two measurable outcomes: financial returns and social or environmental impact. While established methods for measuring and managing risk are used in financial analysis, no analogue yet exists for social impact in the domain of social and environmental impact investing. How do investors keep their promise of creating, measuring, and communicating impact to stakeholders, without clear guidance or regulation about how to do so? This question guides the three essays in this dissertation. In Chapter 1, I draw on 135 interviews and 102 documents related to impact measurement to investigate how impact investors conceptualize and attend to the expectation that they measure their impact. Using grounded theory analysis, I find a marked difference between the practice and rhetoric of impact measurement. Unlike the conventional portrayal of decoupling as non-implementation of adopted policies, this decoupling reflects how individuals deviate from idealized practices while reinterpreting those practices to meet institutional expectations. Then, in Chapter 2, I employ a narrative theory approach to investigate how the impact investors interviewed for this project conceptualize, operationalize, and measure impact risk, including the risks to achieving stated impact or causing unintended harm. As a result of this qualitative analysis, I hypothesize and experimentally test the proposition that investors systematically avoid and discount impact risk-related information in investment decision making. Finally, in Chapter 3, I consider the normative implications of the win-win framing by focusing on one impact investment strategy: investing in women. I interrogate the assumptions underlying the win-win strategy for increasing gender diversity and suggest that these assumptions have the potential to reaffirm the very power structures that have historically excluded and undervalued women in business. I then present an alternative theory as a corrective: intersectionality. I articulate distinctions between instrumental and intersectional approaches to valuing diversity using examples from organizations, and I argue that an intersectional approach to valuing diversity may matter not merely discursively but also for material change.