In a previous study, we explored the use of heuristics at the individual and collective level. In the current study, collective decision-making was further investigated by examining the influence of shared (deployment) experience on generating hypotheses. Groups of Soldiers viewed and assessed images depicting different decision environments: operational scenarios (familiar task) or medical triage scenarios (unfamiliar task). After assessing initial threat risk, groups monitored situations as more information was added. When incoming information changed their assessment, Soldiers stopped a scenario and reported a new assessment. We tested whether experience interacted with the order of low- and high-value cues, familiarity of the decision environment and time pressure. Experienced groups were more likely to stop and re-evaluate scenarios at optimal times (when high-value cues were present), but only in familiar scenarios. This suggests these experienced groups were utilizing cue-activated stop rules that were better calibrated to the familiar environments. Time pressure did not induce groups of either experience level to reassess scenarios quicker. We did not find a difference of individual contribution to discussions across the different groups; more clearly defined roles within the experiment might have revealed variable contribution as expected from utilization of a transactive memory system.