In today’s rapidly changing technological scenario, tech giants revise their strategic alignment every couple of years. As a result, their workforce has to be adapted to the organization’s strategy. Members of the workforce who are neither relevant to the strategic alignment, nor can be made relevant by reskilling, have to be either outplaced (i.e. placed in an another job within organization) or separated from the organization. In geographies like Europe, where the cost of separation is very high, it becomes very important to make the right decision for each employee. In this paper, we describe a simulation based methodology to find the probability and time of outplacement of an employee. These numbers are inputs to a global problem of making the optimal decision for the entire workforce.