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"This is my first IT job, I’ve only been working here 3 months"
Then you need to learn this lesson quickly: YOU ARE NOT THE BOSS. The Boss is the Boss. Not you. You make your concerns known to him then you leave it at that.
"I’m considering talking directly to the owners about this issue" Yeah, going over his head is really going to go down well /s. As you have proven you are hard of learning, let me state clearly: it won't, that was sarcasm. The owners will see you've gone over your boss's head and when he says "I've had enough of this jerk, let's get someone else in" they'll be hard pressed to disagree with him.
"my boss’s refusal puts our operations at risk" Your boss already knows this. Especially as you keep banging on about it. What you're doing here is heading for an unceremonious out-kicking. Your boss also knows a lot more about the business than you do. If he's keeping that machine on Win7 then he probably has some good reasons to do so.
"I want to ensure I handle this professionally" No you don't. You want to force your boss to do what you think he should do. If you were being professional you'd state your concerns, in email if necessary, then move on.
"I definitely feel like I’m going to be used as a scapegoat" That's why you put your concerns in an email (ONLY to your boss, nobody else. Or maybe a sympathetic team member). This creates a paper trail so that if and when they come knocking on your door saying "Why did you let this happen! You're fired!" you can point to that email which proves you did everything you could. (Which they won't by the way. You're an idiot newb three months into your first job. You don't have any responsibility yet. So this isn't on you.)
"I’m also planning on seeking employment elsewhere" It doesn't matter where you work while you have this attitude. Newsflash kiddo: you're the asshole here. You're a newb three months into your first job. No matter what you think you know, you don't know anything. Instead of trying to dictate to others what you think they should do, try to learn why they're doing it differently from what you expect. Maybe you have to find somewhere else now; that boat may have already sailed. Maybe if you approach your boss saying something like "er, sorry I was an asshole, I thought I knew more than I do, can we start over and I want to learn from you" (but obvs phrase it better than that) then MAYBE you stand a chance of getting through your first year.
[Sympathetic mode on.]
We all have to learn this stuff and it takes time. Your boss also knows this, and remembers when he was an overenthusiastic hothead. So while all the above might seem harsh, especially the YTA bit, hopefully it'll cause a course correction (which is my intent here) and you'll be back on track to a successful career in IT. This position may still be salvageable but you need to go in on Monday understanding clearly that it might not be, and that it is your fault. And maybe you need to be fired a few times before this sinks in. Good luck.
- lol. no. everything you said, just... lol. no.
- In the end, this is true for any job. Learn to stop caring that you know better than your boss, and just give the minimum expected and ordered effort. It'll save you SO much stress in the long term. Even if you do manage to improve things, you won't get paid extra for it, so screw 'em. Just do it the bosses way and then shrug when it goes tits-up. Also, always make sure your resume is up to date and prepare to jump ship at the first opportunity for a better paycheck.
  The most important career you can learn is that to your employer, you are neither friend nor family; you are an expendable resource, so treat them the same way.
- I guess this entirely depends on what country you're from. I'm a developer, and I constantly have to deal with ignorant bosses. They push me to write code faster, sacrificing proper planning, architecture, and testing. Then I'll be the one sitting up all night fixing a broken release, because my code doesn't work.
  As the professional in this scenario (the one who knows how to develop software), it's my responsibility to make sure it's done right. My boss isn't supposed to know how to do it, so it's my job to let him know.
  Of course, you still have to have your bosses permission to do it, so I totally agree with OP putting pressure on the boss. It's important that the boss knows what's at stake, and it's OP responsibility to make sure he does. But at the same time, it's important for OP to know why the boss doesn't want to upgrade, he might have a good reason, or at least it would be easier to argue against.
  Again, it probably depends on the country. I work in a country with high job security, but it might be different in other countries (not the responsibility, but the danger of doing your job properly).
- The whole point of this post was to get advice, not to be insulted. I'm new to the field, and documenting everything is a valuable lesson I've learned. My boss can be unpredictable, and there's no good reason for not upgrading a system that only runs a single program and has significant security risks. I already plan to send the CYA email tomorrow and then drop it.
  I'm not going over anyone's head. The employee who needs the machine is the one asking for the upgrade because it's impacting his work. He's been requesting it for 8 months. Your attitude is unhelpful, and you're making faulty conclusions. Just because I'm new doesn't mean I don't have valid concerns.
  I'm looking for advice to handle this professionally, not to be made to feel bad for asking for help. Maybe next time, try offering constructive advice instead of acting superior.

101 comments