[erikwiffin]

This is asking a lot from you, but in your situation, I think your goal should be to build up enough of a relationship with your manager that you feel comfortable telling them that, or realize that that's never going to happen at your current company and find a new job.

I have reports who have told me that they're happy doing what they're doing. I don't see it as a negative at all - they're employees who are quietly getting their job done and I don't have to worry about them leaving for career growth or Peter Principle-ing them into incompetence. It's important that we continue to have 1:1s though. People aren't static, they can change their mind, and I also want to make sure I keep an ear out for little things that are annoying them, and do what I can to make them go away.

[scarface74]

That’s good for you. But how good is it for them for you not to inform them of the existential risks of them not getting better at their job and staying marketable? Even if they don’t want a raise? Every industry goes through changes and you should encourage them to stay up to date on those changes instead of just chugging along on the legacy products.

I met two developers in 2016 who had been with the same company for 10 and 17 years respectively maintaining a PowerBuilder app from 1999 running on Sql server 2003.

The company was happy to let them keep chugging along until the company got acquired by venture capital and they said they “no longer wanted to be a software company”. How do you think that worked out for them?