It's often helpful to put your organization's diverse projects alongside each other and compare them. This is the point of maintaining a portfolio: to treat initiatives like investments and to weigh them against each other, balancing and maximizing the relative worth of these projects through disciplined decision making and resource allocation.
Don't let the word "digital" fool you in all this talk about how difficult it is for digital natives and digital immigrants to communicate. The generational gap between the so-called digital natives and the digital immigrants doesn't actually have to do with technology. The real issue is that the two worldviews that they represent are so different.