My usual way of doing this, is by spitballing an estimate with the team, multiplying it by 2.5 or 3, inventing some meaningless milestones and gantt-charts and

My usual way of doing this, is by spitballing an estimate with the team, multiplying it by 2.5 or 3, inventing some meaningless milestones and gantt-charts and presenting it to an outraged management. Then we haggle down to something realistic + a thin buffer. The management has a sense of control, we have realistic deadlines. Caveat: I work in the financial industry, where the complexity of writing a compiler and whipping up a Tableau dashboard are perceived to be equal.