I'd look at past projects. Some ideas: - How long did it last? - How successful was it? - How hard was it really (novelty, competition, complexity,

I'd look at past projects. Some ideas: - How long did it last? - How successful was it? - How hard was it really (novelty, competition, complexity, regulations, number of people involved, lines of code if applicable)? - What were their mistakes? Which were the most painful? - How did they correct their trajectory? - What will they change this time? But you have to calibrate your expectations with the current project, otherwise you'll pretty much filter any first timer.