I work in tech at a medium-sized company. My team is in the middle of a very frustrating project.
The project has been emotionally draining and the end keeps slipping further into the future. In the past I argued that this project wasn't a good investment of our team's time, and people listened... in the short term. But then a few months later we'd been signed up for this monumental and dreadful task.
My manager and I have good rapport. I have talked to him several times over the past few months about feeling frustrated at work. After a recent chat with him, his boss asked me to meet sometime soon and discuss my feelings about work and "how things are going". I haven't had too much direct interaction with him, but this exchange felt fairly personal.
I suspect that he's gained the impression from my boss that I'm not happy and might consider leaving.
By industry standards I'm inexperienced, but on my team I am one of the most productive developers and a mentor to those around me. I frequently feel like I'm working overtime to keep everything from going off the rails, which is part of what's led to my disillusionment. At this point in my career, I want to be in an environment full of great people who I can learn from, and instead I feel like I'm at the top, with plenty of people to teach and nobody to teach me.
Based on this interaction, I sense that my 2nd-level manager is aware of my contributions and is invested in keeping me on the team.
I don't mean to come at this opportunity from an "everything-is-a-negotiation-and-I'd-argue-with-my-grandmother-on-her-deathbed-for-two-more-vacation-days" sort of mentality, but I do have an admittedly selfish interest in improving my happiness at work. A raise would of course not be unwelcome although I'm already compensated fairly (though not quite as generously as if I worked at a larger company).
Am I being unrealistic to hope that a conversation with this 2nd-level manager might result in substantial changes that would make me happier at work? Like, say, hiring a much more senior developer onto the team, or changing the way projects are prioritized to avoid this sort of drudgery again?
Or, more cynically, should I use this as a lever to boost my salary before spring-boarding to another company?