“Just because you’re afraid of doing something doesn’t give you a permission slip to not do it.”
Debbie Millman.
There’s a lot of fear in OSS. So many things can go wrong (the OctopOSS theory), so much incompetence is created, so many nearly insurmountable integration challenges await and their complexity means that there is no perfect plan going into a project.
They do require a leap of faith, a confidence in your team to work your way through all the challenges and a commitment from senior stakeholders to help drive change through (with compassion for those whose working life is about to be impacted of course). They also need an eye for simplification, like the Mechanical Turk model.
Oh, and I’d like you to have a think about how the momentum spiral or corkscrew model might help you to get from afraid to delivered.