Any project management software out there that takes an ML / probabilistic approach to this? One thing I found at one of the mega-corps that I worked at is that

Any project management software out there that takes an ML / probabilistic approach to this? One thing I found at one of the mega-corps that I worked at is that both project managers and regular managers were blind to history. Note: this was before agile became accepted by mega-corps. Manager: How long is this going to take? Me: Virtually impossible to predict accurately Manager: I need a date Me: 3 months Manager: That's too long, we need to get it done in 1 month Me: OK, 1 month ... 5 months and several iterations later ... Manager: Project has been deprioritized, we have a new project, how long is this going to take? Me: Virtually impossible to predict accurately Manager: I need a date Me: I need you to be stateful.