[tjansen]

Frankly no one wants to hire an engineer who highlights technical debt or a lack of tests without being asked for it. This kind of negative people is annoying and IMHO is indeed a reason why employers hesitate to employ older employees. Many are a pain in the... (and I say that as someone who's turning grey as well)

Most employers want to hire someone who actively improves things, someone who solves issues, and not someone who just complaints about them and makes demands.

[penguin_booze]

Seeing and raising red flags as and when they arise--or even better, even before they arise--is the hallmark of a good employee. If you don't want to hire one such, good luck. That said, there's a difference between flagging and nagging. Again, a good one will know the difference.