Show how support time, time between failures, number of problems should go up if you won't do the change.
Each technology has it's time limits, end of support from the manufacture, and regular life cycle.
Example - if you use MFC - you can show that programming a simple task in MFC is 3 times slower than in winforms. so after x months, the benefit from not upgrading will be lost.
with equipment it is even easier, as the older the equipment gets, the more mal-functions there are and it is easy to show (usually after the 3 years covarage everything starts to break, and I think it's planned like this. it didn't use to be but these days it does).
with infrastructure - again - if you have oracle 7.6 - show how much more time (money) you spend on administration and how less will be spent in 11g.
ect. ect. ect.
eventually manager wants to see ROI... TCO... BLA BLA BLA so you need to give them that.