The Monte Carlo simulation models real-world risk: deals are correlated (bad quarters hurt many deals at once), early-stage deals frequently slip to next quarter, and large deals often close at reduced scope. These factors create a left-skewed distribution. There are more paths to missing the target than exceeding it. A median outcome near target with a lower hit probability means you will probably land close to target, but the downside scenarios are heavier and more numerous than the upside ones.