So what's the other option? Run a system until it has run itself into the ground and can no longer be fixed? A smart CIO doesn't let the institutional knowledge go out the door with the staff.
I've seen more IT projects fail because the IT staff was afraid of being made irrelevant due to an upgrade. Will a COBOL programmer three years from retirement really get actively involved in upgrading a system knowing that the successful completion of the project will put his career in jeopardy so late in the game, even if it's in the company's best interest? Of course not!
So why should a company keep an "if it ain't broke, don't fix it" attitude? All that leads to is needless dependency on people being overpaid simply because their skill set is rare. Additionally, the company probably won't hire two COBOL programmers, so when this person gets sick, or gets hit by a bus, the company is screwed.
On top of all that, when you wait too long to upgrade systems, the upgrade path is either convoluted (e.g., upgrading through multiple software versions), or it simply can't be accomplished at all. In other words, the longer you wait, the harder and more expensive the upgrade will be. Every system will become obsolete, and "it ain't broke" is just not a compelling reason, because all that really means is "it ain't broke yet."
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