<p>Should one make the first or second move in a negotiation? Classic negotiation literature generally advocates moving first due to the anchoring heuristic. However, recent literature endorses moving second under some conditions. This shift calls for a rigorous examination of the contexts and situations in which it is better to move first and those in which it is better to move second. This research examines practitioners’ practices and perspectives regarding the effects of contexts and situations on the benefits and drawbacks of moving first in negotiations. We interviewed forty-nine practitioners and examined their negotiation preferences and the reasoning associated with those preferences. We outline some underlying issues that are associated with practitioners’ reasoning. Thus, we trace the factors practitioners consider relevant to making the first versus second move in negotiations and present a model for determining when to move first or second based on our analysis of practitioners’ perspectives. This research sheds light on possible factors influencing the utility of making the first vs. second move in negotiations. We call for further research to systematically examine those factors to further our understanding of negotiation dynamics.</p>