Hey Everyone,
Background
I was hired for a small company in my area, they company has had one IT \ Programmer \ Engineer for the past 13 years. He has done well on his own for that time and I commend him on this task. BUT, since hiring me, Mid 20’s just out of school and up to date on the newer technologies, all I have done is projects that have been in the works for a year if not longer.
The Issue
I was assigned all these projects and have written up solutions that are cost effective, most completed with Hardware on-hand, and can update or change the way something is being done currently. Most of these are either pieced together or less efficient. That’s when I hit the wall and he fights the idea until he has wasted 100’s of the companies dollars and has been ending up where I suggested.
The Question
Whats the best way to work through this problem? I would hate to have to do things behind his back and let him find out once they are already in place and functional.
14 Spice ups
rockn
(Rockn)
2
Ask him if he really wants you to work there and do what he hired you to do. Micromanagers suck the big one.
7 Spice ups
If he’s your boss, do what he says. It wont be you on the line for costing the company.
1 Spice up
Is he your boss or co-worker?
Thump him in the head with a size 12 doc martin.
Neally
(Neally)
6
Since you new, prove yourself. show him that what you suggest makes sense and works. I know he’s more ‘dsenior’ but try to teach him newer stuff ( I know 2 big pet peeves of old wolves are virtualization and Powershell…)
If he does not listen or doesn’t give a fork, I’d see if you can talk to his boss, or a CIO, or something like that.
If none if that help, at least stick around long enough so it looks ok on the resume (or short enough not to mention the job?) and move on.
2 Spice ups
stopthenoise
(Captain Frostbyte)
7
How long have you been there? In his defense, it’s hard for some to let go of the reins. It may take him some time to start trusting your solutions out of the box. It’s his ass on the line for letting you do it, so he’s leery. What kind of back up are you giving him on your proposals? as you just saying X works lets do it or are you saying i’ve been looking into this, and many companies are doing X and it works well for them like #insert example here#.
3 Spice ups
Robert5205
(Robert5205)
8
Whats the best way to work through this problem? I would hate to have to do things behind his back and let him find out once they are already in place and functional.
Well, you could start with humility and respect. This guy has been solving problems and keeping things running at tis company since before you were out of high school. And, he was doing it with decade-old technology that wasn’t nearly as good as what you take for granted today.
Next, you might bear in mind that he likely has other responsibilities that take up some of his time. No one starts a project with the goal of not completing it. If he has a lot of incomplete projects, then it’s because he ran short of time, money, or other resources.
Finally, look at things from his perspective. A solution that isn’t understandable or maintainable isn’t really a solution - it’s a disaster waiting to happen. So, in addition to solving a technical problem, your solutions also have to be learnable by him. After all, you could disappear tomorrow; what will he do then with a pocketful of your cost-effective modern solutions that he can’t maintain? Ultimately, he’s responsible for how things run. And I bet he’s seen a lot of good ideas that didn’t pan out in production.
If you really want to succeed in this job, understand that part of your job is making your boss comfortable with what’s going on and working to meet his needs, not yours.
18 Spice ups
bhefty
(Brit Hefty)
9
This is one of those smaller / bigger picture things. He’s got 13 years of dealing with this company and getting to the point where he can waste a couple hundred bucks of the companies money without getting pinned under the microscope. You’ve got to make him see the value in it, just like you need to make a CIO see the value in it, just like anything else. Just because he is IT doesn’t mean he is going to just take your word without scrutiny. Yeah you could wash your hands of it and move on, or you could develop a rapport with him and engage in conversation, finding a middle-ground solution.
4 Spice ups
bob-13
(Bob_13)
10
Well, it is “his party” and I’m sure he’s on the hook more than you are as he’s the one who always made it work before.
That said, try and broach the subject of:
I have ideas and I can explain them, or I can (where possible) demo them. “Someone” trusted me to do this job, and sure I will make mistakes, but which is better, each of doing our best, or you doing twice the work by checking into all the stuff I’m doing? I mean you know this environment and what has worked here, and I’m open to ideas but shouldn’t I be taking some of the load off you instead of adding to it? If I give you the plan and you have concerns that’s fine, make suggestions, or ask me questions or both.
Basically play the role of “he’s the expert” and you’re “just here to help” until he gets used to how you think. You’ll be wrong occasionally and so will he, built from that. Show respect and willingness to work, but also try to get him to meet you partway.
Or start looking for other work. Basically if he still wants to do it all himself, and he out ranks you… you won’t win so you might as well not play.
2 Spice ups
There’s an old saying about “Don’t come to me with problems come to me with solutions” and whilst I’m not that keen on the phrase, the sentiment stands IMO.
If you’re getting pushback to genuinely good ideas, enquire what alternatives he would suggest?
Can you give a few examples?
The reason I ask is that respectfully, as I’ve grown a little older I do now look at things with more of a “what’s the best thing for the business?” hat on than I did when I was your age, where I saw certain things much more black and white solely on technical grounds.
Basically he might see thing you don’t, or you might be entirely correct and he’s just stuck in his ways 
5 Spice ups
“your solutions also have to be learnable by him.” - Robert5205
I understand and agree that he deserves my respect. But, what can I do if he is unwilling to even learn.
Example:
We just recently updated our old server from 2003 r2 to a new server 2012 r2 and he down graded the new server 2003 r2. He wasn’t even willing to learn or let me try and teach him the benefits of the updated software. Every New PC I install I have to down grade the OS and then install special software that we wouldn’t need if we stayed with the newer Windows version.
You can only be humble for so long before it’s not worth it to you personally or to the company as a whole.
I tend to think respect is earned rather than conferred simply because you’re older, but that’s possibly just me being young and disrespectful 
The maintenance point is an interesting one. Read another way, the way I would read it, do you potentially hold the company back because some of the staff you have aren’t willing or able to learn new technology?
Not suggesting that’s the case, but I could see it being very frustrating if (and of course we don’t know if this is the case) the OP is suggesting things that pretty much anyone takes for granted yet is shot down because their boss hasn’t really moved on from the year 2000.
Yep, that was stupid since it is no longer being supported by Microsoft.
1 Spice up
Kenny8416
(Kenny8416)
15
Try to flip this situation on its head though - have you asked him WHY he downgraded the server, have you asked why he’s not keen on the solutions you’ve been coming up with.
There may well be a good reason. Remember he’s been at this for years, you’re still wet behind the ears. Fresh out of college does not mean you know newer tech that he doesn’t. It means you’ve still got a hell of a lot to learn - be smart, try and learn some of it from your boss.
yes you may need to let some things slide for now, but always ask why, and understand why.
Maybe there are apps that are critical that won’t work with 2012, maybe he’s tried it all on a home lab, and knows just as much about new tech as you do.
Having said that you could be right in that you’re working with a dinosaur, but you won’t knwo unless you talk to him and understand his reasoning.
Lastly, never, ever go above his head and try to tell the upper management that he is blocking your ideas. That will kill any trust between you, will create a toxic work environment, and will result in one of you having to leave (And it probably won’t be him!)
1 Spice up
Robert5205
(Robert5205)
16
All good points. Respect is something that must be given. A person can earn respect, deserve respect, or even demand respect. But if you don’t give respect, then all the wishes in the world won’t confer it. Even if you don’t have respect for the person, you should have respect for the position. You can be dissatisfied or unhappy, think yourself smarter, or be better at something. But none of that justifies being disrespectful or contemptuous of someone.
Your second point is a great one. Let me rephrase it: *Does having a lack of resources hold the company back?* Absolutely. And staff are resources. If you have an HP G4 server that can’t virtualize, that holds you back. If you have an HP G9 and staff that don’t understand virtualization, that’s exactly the same problem. Old servers have some value; so do people with limited skills. But they do present obstacles. So, like replacing hardware, we have to replace skills as well.
Do you think there is any value in first learning what the obsolete systems do and how to maintain them before proposing replacements? We know two things for certain: 1) the current system works, 2) we know nothing about the new system except that we expect it to work.
1 Spice up
“So, like replacing hardware, we have to replace skills as well” is kind of my point.
The specific example given was:
“We just recently updated our old server from 2003 r2 to a new server 2012 r2 and he down graded the new server 2003 r2. He wasn’t even willing to learn or let me try and teach him the benefits of the updated software.”
Now fair enough, we all know there are three sides to every story and we only have one side here, but if you take that at face value, that’s someone simply not keeping current nor wanting to do so.
Of course as you say there may be some very valid reasons that 2012 r2 isn’t an option, we don’t know.
I do know that personally I’d have a hard time biting my tongue if I was sure that bad decisions were being taken simply so someone didn’t have to step out of their comfort zone - I’d also like to think that if it was me making the bad decisions my colleagues would pick challenge me on it.
Bud-G
(Bud G.)
18
Aside from some of the great wisdom already offered, I’d make sure you keep records of the pushback. Be able to prove to people (management) that he pushes back on your ideas then comes to terms with them AFTER he has been unable to figure out something better.
Maybe go to the person and ask WTF you have to do to prove yourself to him. Sometimes these kind of people wait for you to push them back to show that you can stand up for yourself.
A few years back, as a technical writer, I had to deal with someone like that. He was the lead writer for the team. A lot of what I said made sense, to me, but he saw it as a challenge to his self-perceived “authority.” I learned to basically give out my idea, have him argue everything against it, until he wound up convincing himself that it was a great idea that he had thought up all on his own. The best part was our manager knew what was going on and would just laugh when I did it.
Worked out well for our team.
colinkent
(Colin Kent)
19
All very good advice thus far,However most of these situations are untenable.
Learn what you can, keep your head down and look for a better boss at the next gig.
weirdfish
(WeirdFish)
20
Calling it stupid is premature.
We don’t know why the boss insists on downgrading. OP left that part out.
It could be, as many of us tend to presume and want to believe (because we here on SW tend to have that pack/mob mentality going, even if it’s not the right way of thinking) that the boss is simply a moron. That may be true.
OR it could be that the boss a) knows his coworkers better than the OP and knows that upgrading to the latest-n-greatest technology does not automatically translate to “perfect workflow” or b) there are legacy applications being used that cannot be updated to work on latest-n-greatest OSes (for multiple and valid reasons).
We do not have that information available to us to provide an accurate, objective assessment.
I’ve often questioned my sr. network admin’s decisions, but every time I did, I was proven wrong. And I’ve worked with him for 15 years (he was my boss previously, and quite frankly, I see him as a mentor and friend). Despite that much time, he still amazes me with how his mind works and exactly how much of the big picture he sees. I thought I was good at big picture thinking, but he puts me to shame.
And this is not just 15 years in the same organization, but close to 20 years in the industry itself.
1 Spice up