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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?

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    they're probably already weighing up a replacement for you – Kilisi Jun 21 '16 at 1:52
  • If they're smart, then yes. But I don't fear being laid off. As I mentioned, this is a fairly small company and a very small team. Me (or anyone on my team) being fired would come as a pretty huge surprise to my colleagues, and would put a heck of a dent in morale. – bradp_ Jun 21 '16 at 1:58
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    you would know better the particular circumstances, but as an employer if I did get an extra experienced staff member, in the back of my mind would be getting rid of the guy who can't handle pressure as soon as the experienced guy could take over. Morale wouldn't take a big hit that way. Morale is taking a hit right now because the go to guy (you) isn't stepping up to the plate. When the leaders are walking around depressed, it affects everyone. No offence, but that's how I'd see it. Probably better long term for you is to change into a more suitable role. – Kilisi Jun 21 '16 at 2:14
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    No offense taken; that's a valuable perspective I hadn't considered. – bradp_ Jun 21 '16 at 2:17
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    Huh, well I suppose it's good if they actually care about retaining you. In my industry (defense), employers generally couldn't care less about turnover. Projects tend to drag on for years and there is a constant churn as people get burnt out by the "never-ending hamster wheel of scrum" and move on. Two years on a project with no end in sight is about my limit (which is about my average job tenure if you look at my resume, not a coincidence -- retaining me would be a simple matter of shifting me to a new project every once in a while, but apparently that's a bridge too far). – James Adam Jun 21 '16 at 12:01
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This is something you need to make a decision about, we can't make it for you. I'm going to point out some options from how I see your problem, I may well be wide of the mark. To me the basic problem is that you're in a role you don't feel suitable for, or perhaps ready for.

If you're at the stage where you are seriously considering leaving then that is probably the best move for you. Expect to upset your bosses if you do so, because you'll be leaving them a mess. But always put your own needs first, especially if it affects your health.

If it's the just the project that is getting you down, then perhaps that could be rectified by an attitude adjustment. Frustration is a bad enemy to have around, it's something a lot of people deal with, some better than others, here's my strategy which has worked for me over the years, your mileage may vary.

Being the go to guy is a lot of pressure, but you set the tone for a whole team. I'm the go to guy for a lot of people, I am successful because when things go South I'm walking around like a carefree butterfly wearing a big grin. The bigger the problem, the wider the grin. That's how you boost morale and get a team pulling together and solving problems. The physical act of smiling at problems makes the burden lighter and lessens frustration.

However some projects are just ridiculous and should be chucked in the bin where they belong, so that's a judgement call. Personally I have taken projects to fruition and got enormous satisfaction from doing what was breaking other people in the attempt. Getting the team behind me 100% was a large part of the success.

This is a bit like a make or break moment in some ways. Expecting the bosses to solve your problems puts pressure on them, which may pay off short term for you, or may work against you. Long term though, if you decide to stay with the company, taking the pressure in your stride will give you a huge rep boost.

If you're determined to chuck it in, then get what short term benefits you can, mentally you already have one foot out the door. You can start thinking long term in your next job.

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    agree with the 4th part. I am too the "go to guy" and since I am always smiling and saying people that it will be fine and so on, the project is going smoothly with no problem, and people are not too frustrated :). – Gautier C Jun 21 '16 at 7:43
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    Very good strategy here, though don't look overly happy (people might think you do not care or project goals/deadlines are not important). – B1313 Jun 21 '16 at 13:52
  • Looking positive, confident, focused and unstressed is what you're trying to achieve. It makes others around you the same and makes a huge difference. I've been in some very extreme disaster recovery situations and seen a lifting of tension and stress as soon as I walk in. Everyone becomes focused on solutions rather than unconstructive recriminations and crap. – Kilisi Jun 21 '16 at 14:30
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    +1 Great advice, plus what you put in the comments. When a big boss wants to talk about "how things are going", it's the first step to finding a replacement. – Retired Codger Jun 21 '16 at 16:11
  • The bosses can be upset, but they created the mess by disregarding his advice. – kevin cline Jun 21 '16 at 22:28
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I do have an admittedly selfish interest in improving my happiness at work.

This isn't a selfish thing. Full-timers spend an extraordinary chunk of their time working. They see their co-workers almost as much as they see their families and more than they see their friends. No position will be perfect, but there's no sense remaining in a position where you are frustrated, defeated, and miserable due to factors outside of your control - especially if you're in-demand and have other opportunities. It's too much wasted energy, to much of a drain on your life.

Having said that, talk to the 2nd level manager. I won't venture to guess what to expect from that discussion; we are undoubtedly missing a great deal of context in your situation, it's the nature of the Workplace beast. Maybe it will go your way, maybe not. Regardless, it will help you decided your next steps if you want to stick it out or start looking around for other work.

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I believe you should tell them exactly what you told us and add that you fell you should be used better by the company, given some technical lead position or sub-management position so you can slowly step away from development and progressively boost your manager/team leader skills (by of course studying and learning a lot) so you can stick to the company AND progress on your career.

A salary boost is always good, but you will be in the same unhappy position in a few months. Progressing on your career, on the other end, gives you a totally different set of targets to achieve and personal challenges.

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