The boss signs off on the project, but he's not really technical. it's up to us to do the TCO on the upgrade, and the cost/benefit analysis. Plus, we have some of us testing to see if it's compatible,

If the boss wants to upgrade, then we can say that we've looked at it and here's the TCO and CBA, and if you really want to do it here's the cost and timeline.

In our case at least, the boss will turn sickly green at the cost and ask how long we can stay where we are.