One estimation method I found good and worked at a risky project in my job (involved a regulator, they love deadlines) was: 1. Do the usual breakdown of tasks

One estimation method I found good and worked at a risky project in my job (involved a regulator, they love deadlines) was: 1. Do the usual breakdown of tasks and point game to get relative difficulty estimates 2. Calculate the std dev points for each task instead of just averaging. The assumption is that this is valuable information about how uncertain developers are about the task, so we don’t want to throw it away. 3. Create happy-path and worst-case scenarios considering +-1sigma and +-2sigma 4. Prioritize tasks by deviation, to remove the most uncertainties at the beginning of the project With this you start w/ a more realistic view of the uncertainty of the project, and it’s supposed to converge to the avg as the project goes.