There are many occasions on which the critical decisions should be made in software projects. Those decisions are basically related to estimating and predicting project parameters such as costs, efforts, and duration. The project managers are looking for methods to make better decisions. The decisions about project parameters are recommended to be performed based on historical data of Similar projects. The measures of the tasks in past projects may have different shapes of distributions. we need to add those measures to get a predicted project measures. To add measures with different shapes of distribution, we need to use Monte Carlo Simulation. In this paper, we suggest applying Monte Carlo Simulation for supporting decision makings in software project. We implemented best-fit case and scheduling estimations with Cristal Ball, a commercial product of Monte Carlo simulation and showed how the suggested approach supports those critical decision makings.