Knowledge transfer around retirement only works if you start 3 to 5 years before your senior engineers leave. If you wait until someone actually walks out the door, the knowledge is already gone: it lives in heads, not in documentation. Organizations without a plan today will soon be buying expensive interim solutions for problems that were preventable.
You probably have him on your team. That one engineer who understands the legacy system. Who knows why that odd workaround was built in ten years ago. Who you call when things really go wrong, in the middle of the night.
That person is going to retire. Not in twenty years. In a few years.
And you have no idea what happens then to the knowledge he takes with him.