Machines are increasingly becoming a substitute for human skills and intelligence in a number of fields where decisions that are crucial to group performance have to be taken under stringent constraints—for example, when an army contingent has to devise battlefield tactics or when a medical team has to diagnose and treat a life-threatening condition or illness. We hypothesize a scenario where similar machine-based intelligent technology is available to support, and even substitute human decision making in an organizational leadership context. We do not engage in any metaphysical debate on the plausibility of such a scenario. Rather, we contend that given what we observe in several other fields of human decision making, such a scenario may very well eventuate in the near future. We argue a number of "positives" that can be expected to emerge out of automated group and organizational leadership decision making. We also posit several anti-theses—"negatives" that can also potentially emerge from the hypothesized scenario and critically consider their implications. We aim to bring leadership and organization theorists, as well as researchers in machine intelligence, together at the discussion table for the first time and postulate that while leadership decision making in a group/organizational context could be effectively delegated to an artificial-intelligence (AI)-based decision system, this would need to be subject to the devising of crucial safeguarding conditions.