In response to widespread concerns about litigation costs and ‘access to justice’, lawyers generally accept that assessing risk is an inherent dimension of their work. Many still prefer, however, vague and imprecise conversations about litigation risk. This paper presents the results of an empirical study, exploring lawyers’ experiences with risk assessment approaches and tools. It identifies challenges and ‘turning points’ as lawyers wrestle with risk projections. It also outlines a simple, practical framework for guiding litigation risk analysis. A lawyer who is well-rooted in the foundations of the risk assessment task will, we suggest, be better able to provide full and transparent assessments – to the client, and even to a mediator who may be facilitating settlement conversations.