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Tl;dr: I am not getting the tools and knowledge required in order to complete my job effectively, despite repeated requests and attempts to do so. I want to keep the job and be good at it.

How can I achieve and excel in a civilian job where the leadership essentially refuses to allow growth?

My title is 'network administrator' (and DBA, SysAdmin, Developer, Programmer, Tech Support, etc etc) for a small company (450 or so personnel). There are only two 'IT' persons on site to handle everything related to technology. Myself, and my boss. I have been employed a little over a year and am still adjusting to the different style and environment of the job. Previously, I was a soldier with 6 years service; this is my first civilian job. I was a soldier, I was in an intelligence MOS (laugh all you want) and I am a smart guy. I know how to follow orders, I know when to clarify the situation, that my actions must fit my orders. I have no degree however, due to going into the military instead of college. I believe this is why my boss (apparently) looks down on me.

When I was hired it was with the understanding to 'learn and develop' as much as I could about the field I am working in, in case he encountered a 'hit by a bus' event. He has been with this company as the sole IT person for the past 26 years. The systems they use are mainly Windows systems, but with a few industry specific servers/applications (AS/400, BLIS-400, EDI/ERP systems, Lotus (ugh) notes etc). It was my understanding that I would be trained and brought up to speed on these systems due to being unfamiliar with them. I was not to touch any of the systems (mission critical) until I had the proper training. Without this familiarity, I could not support the systems or personnel using them.

It is over a year later, and my 'training' for these systems was 1 session each: How to login, and change your password. During this year my duties have been relegated to performing help desk level IT support, a bit of web developing, and general maintenance/updates of the Windows and Linux systems on site. I do not begrudge that; it is after all, my job. However, during this past year I have also constantly asked my superior for training on the BLIS-400 or Notes systems. Every request, verbal or written was met with 'when it slows down/when we have time' or 'Okay, no problem'. Nothing has come of this.

Constantly, during my job I am approached by co-workers who begin spouting off their IT request/issues, drop a piece of paper (or post it) on my desk, and leave. (This place has no offical help desk software, request are generally done in person, stopping in the hallway, etc). Most of these request involve the systems I have no idea or control over. Therefore, I pass the information on to my superior with a personal request formulated such as "SB1 has asked me for CF6. I would do it, but I'm unsure of the proper procedure/method/protocol/system permissions to get it done. Is this something you can handle, or explain to me how to learn to do it so I won't have to bother you again?"

Nothing comes of this. My boss will 'take care' of the issue with a slight nod, or an email with my CC'd - "Its done". Follow-up questions on what was done or a quick primer are ignored, handled much in the same manner : When we have time or Don't worry about it, its done.

I have attempted to get the company to purchase books on AS/400, send me to classes/conferences, or to other sites to learn the system. I know my superior is busy and cannot take time away from his duties to ensure I am 100% trained. (But, it would be nice.) I have offered to even come in on a weekend to learn at least the basics and go from there. This, has never been met with enthusiasm or acceptance. I still know how to login to the system and change my password. If anyone here has dealt with IBM iSeries, AS/400 or the BLIS system built on top of it, you understand the complexity of the program, commands, and libraries. To me, this is not something as simple as 'Dive into AS/400' and within a week or two being up to speed enough to manage.

Recently, my superior went on a vacation. I was informed of this on the day his vacation began with a 'rundown' of how to perform tape backups. I know the man is under no obligation to inform me of his schedule, however being told in advance of such an event would allow me to prepare for it adequately. On top of that, I feel he insulted me by attempting to 'train' me on how to use a common and very widely used backup system and methodology.

During this hiatus, There where many projects and issues crop up that I was completely unaware of. That is, management requesting status and information on IT projects that 'we' where working on. ('We', because I had no clue to them even existing let alone my hand in completing them.) There where also a few general issues with improper parts or orders that needed to be changed in the system. I had to inform various personnel that I could not assist them in correcting the mistakes, they would need to wait a week and ask my superior to do so. The looks alone from co-workers where bad, but one even had the gall to state So you can't do anything and they still pay you? Must be nice. On top of that there was a major issues with the system that required certain commands to be run, queues to be changed, and slight programming modifications before shipping could continue. Due to my inexperience with this system, I had to call my superior on his vacation, explain the situation in a voicemail and wait for him to respond. In a very time critical situation (shippers waiting to depart dock) it took two hours before my boss responded to me. In an email. "They can ship, its fixed."

That, is the back story. Yesterday, my boss returned to work. I continued with my duties, briefing him of the most important issues during his departure and awaited further orders. Today, I asked him if there was any projects, duties, orders, menial tasks he would like to assign me so that he could have a better workload. A few tasks where given to me, but by lunch time (actually, 45 min ago) these tasks where completed. I am now without orders and so I again ask my superior 'Any other tasks you need me to complete, or perhaps is now a good time to train on the BLIS-400'. His response, filled with what I took as malice, was "Christ, I can't hold your damn hand for everything. You'll have to learn it the same way I did. Get in there and mess around, figure it out. I'm not babying you."

Now I'd like to say, that I am far from being 'babyed' at this job. I take initiative to do things that need to be done, within my authority. I 'Get shit done', and there are no complaints from my boss that I know of. Those above him in the chain of command also applaud my work ethic, drive, and desire to help. I have a great boss as far as bosses go. He is laid back and allows me the freedom to work autonomously. He always backs me up when an issue arises and is willing to let me challenge the way IT things are done in order to improve them. Overall , I feel he is a rarely good civilian manager. His flaw, and the source of my frustrations, is his lack of communication. In a year of working, in the same (large) office, the most we have spoken verbally is standard salutations. A few communications over email for clarification on projects, or me passing along information that he needs to act on. He never initiates a conversation with me, and in fact, I have to specifically ask him for 'work' or a task before he will tell me what is on his project list.

This lack of communication and that phrase, is what brought me here. I cannot fully do my job because even a year in, I have not been equipped or trained to do it. I complete every task given to me, and am always seeking more to do. I cannot be content sitting around, idling the day away. There is always something for me to do, but at this time, 90% of the projects I should be handling are on systems I know about 0.0316% of. This is not conducive to me retaining my job, which, I do like and want to keep! However with continued lack of training, lack of communication, and multiple personnel essentially seeing me as 'not doing anything', I am afraid of losing my job. I need advice please on how to address this situation professionally and quickly. I need to get the situation and especially my skills up to speed soon, without alienating my superior or over stepping my authority. I do not want to work in another position in this field, I just want to do the best I can at this one.

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    The question as it is now seems to be very localized. I think it could be easily improved by condensing it (a lot) and generalizing the situation. – René Wolferink Mar 19 '13 at 17:18
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    Honestly, the thing is not too long and he has a genuine work-related problem. I don't get the down votes and close votes at all unless people are just too lazy to read. Lots of pepoel have bosses wh are trying to make sure they fail. There is nothing localized about this problem. – HLGEM Mar 19 '13 at 17:26
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    RackLackey : sorry for a personal remark - please change your nick and attitude first. You are not a lackey. Your job is keeping the keys to the corporate kingdom. Next, you have to fish out the manuals for all the systems in your realm, and read them thoroughly, then again and again. Make notes on sequences of DANGEROUS commands, and yes, experiment on testing machines (not on production ones! and make sure there are backups). You have a lot of things to learn, and do not expect orders - build your knowledge base first, then you can get to the level of your boss or surpass him. – Deer Hunter Mar 19 '13 at 21:03
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    Please do not take what (and how) he said to you about babysitting as malice. He may be frustrated with your attitude as well. In a nutshell, he (possibly, as I read it) expects more independent thinking from you. Don't get emotional or insulted about using the "common backup system" or anything else - your skills are not written on your face. And learn, learn, learn... – Deer Hunter Mar 19 '13 at 21:10
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    Hi RackLackey, I wanted to address the comments about the length of your post. Quite frankly, conciseness is more likely to get you better answers. Long, wordy, or ranty posts are harder to read and asks a lot out of a community of folks who are volunteering their time to help others. My suggestion would be to edit this down to remove anything that isn't really necessary for posters to post an answer to the question. In short, help others help you. Hope this helps! :) – jmort253 Mar 22 '13 at 1:27
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Wow. He is overworked, and he has a process and a mental model very different from yours. Here's what I see in his behaviour:

  • the problems that people ask you to fix feel like "one-offs" to him - not worth taking the time to show you how to do them, just do them and move on
  • he (and the others) like their current no-process no-tracking approach
  • he doesn't care whether you have anything to do or not, and feels that when you have nothing to do, you could try learning stuff yourself

So, what can you do specifically? First, you could get some sort of issue tracking system in place. TFS is free and I happen to know it, there are others I am sure, heck you could use a Sharepoint list or a spreadsheet. Whenever you become aware of a request, log it. (At this point, don't try to get anyone else in the company to use it. Just use it yourself to handle the requests people drop randomly on you.) See if you can get an idea of urgency. When it's solved, log that too, and if you can, log what the fix was. Over time, you can use your tracker to look for patterns and be in a position to make suggestions.

Second, when you get a request and it's not urgent, you could try to see if you could figure out how to do it instead of passing it along. If it is urgent, instead of "Joe has forgotten his password and needs it reset" you could try "can you show me how to reset passwords so I can help Joe?" (Not when he's on vacation. Minimizing disruption to the vacationing person wins in that case.) If you start with "Joe needs a new password" he can just grunt and do it. If you start with "how do you change passwords?" you might get told how. Also, do this IN PERSON so if he just does it, you have half a chance of seeing what he did. If you email him, and hope he will email instructions to you, keep right on hoping.

If you get pushback when you ask him to show you how to do it, here's where having a tracking system helps. You can say "this is the 5th request this month for that same thing; if I could do it, you could just leave those things with me and not get interrupted." In an ideal world he sighs, says "you might have a point, kid" and shows you how to do it.

Third, in your free time you can write up some sort of process manual - how to do all the things you don't know how to do. This is basically an organized copy of the "results" section of your tracking system. At first it has no instructions in it, but as you learn some or all of how to handle something, you can add to it. You can monitor what requests come in and try to see what is different afterwards, or even ask him "when you have a minute, can you show me what you did to fix Steve's problem? I wouldn't have even known where to start on that one." The existence of this manual will be valuable to the company and make sure that you don't end up later being the guy who doesn't have time to explain all this to the new guy.

Fourth, if you're able to talk to the person who hired you, try to find out whether it was your boss' idea to have you here. He might like feeling indispensable and not like you knowing his trade secrets of how to keep the company alive. In that case, you might be between a rock and a hard place.

You are getting a little bit of feedback from your boss, even though it's hard to parse. Keep in mind that a question (how do I, what should I, where is) is not the same as telling (I'm going to try, Joe asked me to) and he might be fine with your announcing you are starting - that way he can stop you if it's something very hard or delicate. And if his positions are contradictory you are allowed to say "but yesterday you said XYZ" and let him either realize he's being unreasonable or (and this is crucial) clarify his positions for you so you see they are in fact consistent. It could happen.

  • Thanks for the reply, I wanted to address a few of these points in the original question but it was already pretty long. HelpDesk: I took the initiative to setup Spiceworks (which includes a helpdesk) and documentation for employees to use it. Superior stated 'not even going to bother, no one is going to use it'. Hiring Manager: No longer works here, new HR drone. how to do all the things you don't know how to do. <- that is an impossible task. If I knew, I wouldn't be asking. – user8291 Mar 19 '13 at 17:33
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    Got it, thank you. I will begin keep those records. – user8291 Mar 19 '13 at 17:47
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    @RickLacey you get reamed for not notifying him, or you get reamed for trying yourself? Getting reamed for trying yourself is completely at odds with "You'll have to learn it the same way I did. Get in there and mess around, figure it out" If he wants to be notified, tell him I am working on X for Joe, but still try it yourself. – Mr.Mindor Mar 19 '13 at 20:14
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    Everything said in the post, except that TFS is not free, and is not well poised to handle a lot of issues outside of Microsoft development. Get any one of the dozens of issue trackers from sourceforge and the like. Those really are free, because you don't have to keep a MSDN subcription handy. – Edwin Buck Jul 14 '14 at 3:13
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    @EdwinBuck TFS Express/VSO is free for up to 5 users, although I agree that it's not a great choice in this context. It's fantastic at Agile project management, SCM, build, etc, but it's not intended to be used as a ticket tracking system for general IT issues. – Daniel Mann Jul 14 '14 at 7:45
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Some things to consider:

  • In the military, things are incredibly structured. You (likely) had significant structured training to ensure you could be brought up to speed quickly.

  • As someone with 26 years experience in IT, your boss likely had the exact opposite - no training, completely on the job learning, and likely still has completely on the job learning for any and everything that he does

You should realize this puts you both at complete opposite ends of the spectrum of "how have we learned how to do our jobs?"

The only real way to resolve this is to reach some compromise:

  • You need to realize your boss is probably terrible at even considering how to explain things in ways which resemble your military training. It's incredibly likely that concept is as foreign to him as if you asked him to teach you in swahili. Your frustration about your boss's complete lack of cohesive training is likely the same level of frustration your boss feels about your "lack of initiative" or "need to be babysat." This is worth thinking through for a bit...
  • You should have a serious conversation with your boss about this issue (or you'll go insane)
  • My guess is this boss did not initiate the paperwork to create the position you currently have. Find out who did, and if all else fails, talk with them.

Also, when you get requests, stop phrasing them in such a way your boss can just do them. Say, "someone needs XXX. Can you show me how to help them?" and press your boss to help you with this. Many sys-admins are notorious for this sort of thing - "oh it's just easier to do it than teach so I'll keep doing if for months and years and decades."

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    +1. It may be though that the OP already knows kiswahili and a few other languages to boot... – Deer Hunter Mar 19 '13 at 21:33
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    +1 - My last boss just did not get that some people prefer structured and planned to loosey goosey and unstructured. I am of the do it and do it right the first time camp, where alot of IT folks are just try if it isnt perfect just do it over and over until you find something that works. That attitude makes my head explode. – IDrinkandIKnowThings Mar 26 '13 at 18:55
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Your boss looks down on you because you are a direct threat to his job stability. It's not about your lack of college, it's not about your youth...you have the ability to upset his apple cart. His biggest tell was how he handled the vacation situation. He didn't inform you he was going out on vacation, leaving you to handle all of the negative reactions and perceptions from your customers because you weren't adequately prepared. Then, when you relent to call him while he's on vacation, he resolves the problem remotely, demonstrating once again, in his mind, just how vital he is to the survival of the organization. In actuality, he's doing more damage because the company has to literally wait for him to become available to respond to their needs.

Two people supporting 450 employees is a very bad ratio for productivity. He likely doesn't feel he is in the position to return to the job market and start over with a new organization. That being said, the more he teaches you, the easier he will be to replace. I'm willing to bet the organization tolerates him more than they value him, because, to them, he's really the only game in town and they recognize how difficult he will be to replace, given the number of different platforms they are supporting. So, they are simply waiting until they are forced to do something about it.

How do you deal with it? I wouldn't. You were hired to do a job. Doing that job requires knowledge transfer. If he isn't willing to provide that service, it's just going to take you that much longer to be productive, which is a waste of the company's resources. If you can't find someone in the organization to help you address this issue, I would recommend finding another position. Use this experience to help craft quality interview questions for your prospective employer. If his insecurities are keeping him from recognizing that he has a quality subordinate ready to work for the good of the company AND if the company hasn't yet recognized how much of a liability he is to their overall productivity, then it is clearly not a healthy situation for your career progress.

  • Your boss looks down on you because you are a direct threat to his job stability - Do you have anything to back that up? I can buy that the guy likes to feel indispensable but I do not see the feeling threatend. – IDrinkandIKnowThings Mar 26 '13 at 18:57
  • You've been with an organization for 26 years, and have been their sole source of support for the vast majority of that time. The company suddenly changed direction last year, and realized, "Hey, something could happen to him and we could be screwed." So, they hire a new person to protect their interests, which, from a management perspective is the thing to do, even though it's taken them a really long time to do it. The boss is not actively making an effort to help the organization by making his area more productive or offering a reasonable contingency plan in case the worst does happen. – Neil T. Mar 26 '13 at 20:37
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    The less he shows him, the longer it will take for him to get up to speed, which also translates to the longer it will take for the company to be able to transition him out of his position. – Neil T. Mar 26 '13 at 20:38
  • I think that is still a big leap to make. I am not saying it is not possible just that the leap to that as the problem first is unreasonable. It is more likely that the boss does not want to waste time training randomN00b04 just to have them take the skills he taught him to another company a year from now and have to start all over with randomN00b05. But even that is a guess and I have nothing to back it up. That is all your answer is too. – IDrinkandIKnowThings Mar 26 '13 at 20:45
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    I'm not saying that he is being groomed to take over for the boss. I am absolutely saying that the company brought him in to support the boss. What I am also saying is the boss could view the company's decision in hiring support as him training his eventual replacement, which he clearly does not want to do. In his mind, he's been running things on his own for more than 25 years...why do they think he needs help now? I'd be very curious to find out whose idea it was to hire this person in the first. Based on what I've read, I'm willing to bet the boss didn't ask management for help. – Neil T. Mar 27 '13 at 2:09
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I'm not sure this situation is salvageable. But the hint is that he told you to learn the same way he did - by playing around. So you could take something like Lotus Notes (that at least has books available to read) and start to do the help desk tasks that come in. If he questions why you are doing that, tell him that he told you to do it when he told you to learn it on your own. Do you have dev servers that you can't harm? Go ahead and start to learn how to do things. Don't ask him to train you, but see if you can simply observe and take notes.

Frankly, I think you are caught in a situation where you having knowledge threatens your boss. I don't think he is ever going to help you get that knowledge because then he is replaceable. He sees you more as his replacement than his subordinate. In your shoes I would start looking immediately because you are clearly now in a position to get fired because you failed to perform when your boss was absent (something he most likely intended). I know you said you don't want to find another job, but after the disaster of his vacation, I think you need to protect yourself financially and find something before you get fired.

  • Thanks for the reply. His desk is opposite mine in the office, our backs are to each other. I could not watch what he does without actually moving to his location and it being obvious/distraction. I fear you are correct with your statement of him being 'replaceable'. I don't see it like that, I just want to learn, to do what I can and to help. He sees me as encroaching. – user8291 Mar 19 '13 at 17:36
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    @RackLackey - Woohoo, the bit about "encroaching" kind of changes the situation completely. Think you need to amend your question to reflect that. – Deer Hunter Mar 19 '13 at 21:15
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    @DeerHunter That is my speculation, not fact. I don't feel it should be in the question as I cannot prove such. – user8291 Mar 20 '13 at 11:55
  • It is highly likely that he opposed bringing someone on board for your position . – HLGEM Dec 23 '15 at 23:17
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I could baby you and say what you want to hear OR I could tell you what is probably really happening, even if it is probably not pleasant. It seems obvious from your post and your responses to others posts why your boss is the way he is (from your point of view).

I have a team of developers working for me and there are some who I can tell them what problem needs to be solved and they eventually come back and say problem solved. There are others who always come back with excuses and then I have to tell them specifically HOW to solve the problem. Once I tell them HOW then they are competent enough to go off and solve the problem. Experience level isn't even a factor between the 2 kinds of people I just described. It's just that the second group (needs the HOW) always seem to have excuses for why they can't solve the problem.

In looking at your post and replies, I see nothing but excuses. I can tell you from personal experience that those people who usually need the HOW and usually have excuses are very trying on one's patience. Why is it that some people can take totally unfamiliar tasks and figure out how to do them just fine, while others can't take on tasks that are similar (but different) to what they already know and still can't figure it out without help?

While I don't know your boss personally so I can't say one way or the other, but I think many posters have taken a big leap in assuming that he is just afraid for his job. I think absent any other information then it is 50/50 between you or the boss being the problem. However, given all the excuses in your replies, I think that percentage is probably more like 95/5 that he is losing patience and his remark about "babying you" and "figure it out" is because he hasn't seen the initiative in you to solve the problems and/or learn the systems on your own. For instance, there's no excuse for you not to have learned Lotus Notes on your own as you have been there for a year and you know that it would be helpful for your job. There is such a wealth of information on that topic freely available. Someone with initiative would have learned enough to be useful in that area many months ago. Also, employees with initiative are usually able to "find" useful activities on their own when their queue is empty/slow. It is amazing how employees with initiative are always finding opportunities for themselves while other employees are always griping on how they aren't getting to do new things or can't get promoted. It is no accident that this is the usual way things work in the business world.

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    If he's instructed not to access mission-critical systems without training, then doesn't receive the training, then it's his problem because he lacks initiative? Oh, sure, he could learn the systems "on his own", but then if he actually does something to help, the boss could always come back and give him static because he didn't wait to be trained properly, which meant "the way the boss would do it". I don't know how much technical experience you have, but you don't just go changing things without understanding the potential side-effects. – Neil T. Mar 26 '13 at 20:49
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    @Neil - sounds like another excuse. It has nothing to do with "potential side-effects" that's a red-herring. The real issue is that you can sit on your hands and wait for your boss to tell you what to do and how to do it because you are so afraid that your boss will give you static if you are wrong or you can be proactive. If he wants to keep the job and become valuable, sitting on his hands is the wrong way to go. – Dunk Mar 26 '13 at 22:11
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    Also, "refuses to allow growth"?????? How on earth does a company refuse to allow a person to grow? Does he have to stay there 24/7? Is it in his contract that he can't learn anything outside of training received at work? Like I said, nothing but excuses. I can't cover the specifics of his situation, but there are ALWAYS ways to make yourself valuable and grow in your chosen career, regardless of any training the company may or may not offer. Blaming the company, your manager or another employee is not taking responsibility for yourself. – Dunk Mar 26 '13 at 22:15
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    So, basically, if a person isn't a natural self-starter, then you can't be bothered with them? As long as they get done what you feel they need to get done, then you could care less about the "how". Companies don't hamper growth...people do. It sounds to me like he was taking responsibility for himself by admitting something he didn't know and asking for help. There was a clear teaching opportunity that the boss pissed away while he was on vacation. If he's not qualified, then fire him. If the boss considers teaching "babying", then Rack should find another job for his own good. – Neil T. Mar 27 '13 at 3:01
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    @Neil : Why would any company want someone who isn't a self-starter in a position that pretty much requires that ability? Just because someone can get stuff done without being micromanaged doesn't mean they or I could care less about "how". The "how" in the company correct way is part of solving the problem. You are also working on the assumption that the OP knows absolutely nothing about how things work at his company. If he's been there a year, he most certainly should have picked up much of how things should be done, if by no other reason than being there and paying attention. – Dunk Mar 27 '13 at 15:55
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I would suggest this job is a dead end. You're working with the only IT person in the entire company for 26 years. 26 years. That's a damn long time to not practice communicating with another technology professional, and it sure seems like he's not going out of his way to figure it out now. Your military background presents you a totally opposite mode of learning and training than what your boss has been through (26 years, on his own, learning by trying and screwing up). If he's not actively working with you to help teach you things, even after repeated attempts to explicitly request it, you're not going to get it from him. It's likely you were hired as a successor to him, and he knows it and is trying to keep his throne as long as possible.

That being said, to make the best of a bad situation:

  • Take notes. On everything you can. Document how a problem was solved, with as much detail as you can muster on what actually happened to get it done. I'm sure your boss isn't going to give you directions, but if you know anything about how he did it, record it. Same goes for anything you learn, or discover as you're working throughout your day.
  • Explore and test the systems. Obviously, using an appropriate level of common sense and caution, get into the various systems and see what you are able to do. If you have access to manuals or documentation, try walking through operations on a test system. Do it yourself, see how it works, question things that surprise you or make you stumble. Make notes on what to research later, or alternative scenarios to try out.
  • Look for things to improve. Anything that is klunky that could be replaced/improved/reworked with low risk and high payoff, is something you should focus on, technically speaking. Get buy in from people outside of IT, for support in getting it done, and as defense if your boss is irritated by you doing something without permission. Every new piece you put into place yourself is an opportunity to learn, a skill you can add to your resume, and part of the system that you understand and can administrate/support without needing to be subservient to your boss.
  • Keep your eyes open for new employment opportunities. Keep attentive for other jobs/positions outside of your company that seem attainable from the experience that you have acquired. Not trying to be negative, but there is only so much you can realistically do to improve your situation, and perhaps finding a company that's willing to train and invest in a good employee is a better move than staying put.
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Almost every system you list could take one FTE to master, administer and develop for.

The fact that they only have one FTE doing it for 26 years smells bad. Silver bullet syndrome.

Either your boss is a total genius, or he has put together an unstable, hacked system that he administers by hand to keep it going, and the failures are probably adding up every day due to the hacking.

He knows this. And, someone above him probably now suspects this as well.

Dollars to donuts that he was forced to hire someone to "help" him.

If his "help" can figure out stuff quickly and solve problems effectively, he will look really bad.

Therefore, he has no interest in helping you.

I've seen this plenty of times. I'm the consultant that comes in after you quit. My job to evaluate the company's IT department so that management can understand why they have so many problems.

And, 90% of the time, the source of the problem is the company management - their reliance upon one person to "do it all". (i.e. it isn't entirely your boss's fault.)

You should start searching for a new job soon and transition to a place that is properly run.

3

Right or wrong, he gave you the formula for a better working relationship with him. Don't go to him for learning, or structure. Try something on your own.

Find the best AS/400 book you can, pay the awful price for it, and then log into the system and start doing everything you can short of taking the system down. Then find a way to get access to a "development" system and take that one down.

Do keep your boss involved, but at a slight distance. Wait until you have a rather good question (one that shows you tried a few things) and then ask him. If he can answer, some light acknowledgement of his skill and expertise is in order. If he cannot, bow out with something neutral, like "maybe I'm approaching it the wrong way."

In any event, engage him with problems that seem to have a solution, using him as a mentor. He doesn't want to be a teacher, so expect no lesson plan; but, he just might make a good mentor. Basically pop in, tell him what you've tried, what worked and what didn't, and then ask if he has any advice. Then disappear for at least a week or two, popping in to tell him your new status update.

His gruff attitude is a request for you to become self-sufficient. His not teaching you plays into that. Don't work against that grain, unless you really want to try at forcing his hand. Even the attempt of forcing a person's hand comes at a very high cost, you'll lose any chance of a good working relationship.

If you really need the guidance, find a newsgroup or mailing list for AS/400 users. Subscribe and then politely ask for help. The well is dry with you boss, at least until you can prove a bit of what he wants.

1

Thanks for your service!

Job Security

Welcome to the civilian world! Civilians constantly worry about something called "job security", which is something that you never had to worry about in the Army. In fact, job security creates conditions that are 180 degrees from military cross training. If anyone else can do their job, that makes them less valuable to the company, so they must at all costs prevent that from happening, so they can keep their livelihood.

Training, cross training

Lots of civilians will talk about training, cross training, "getting hit by a bus" etc. Talk is cheap, and oftentimes, words mean different things to different people and in different contexts. When they talk about those sorts of things, they are probably platitudes, and certainly not up to par with what you think they mean.

Have a squad full of highly trained and motivated soldiers that can all replace each other if any one of them goes down doesn't translate well into the business and/or civilian world.

Competition to move ahead means that you don't want to share your secrets with your peers, or even that you might sabotage them somehow.

"Promotions"

Your boss has been there for 26 years and just got his first helper. Or maybe you're not his first, but he only has 1 at a time. This guy doesn't know what a promotion is because he's never been promoted. There's no telling what he does or does not think a promotion is. On top of that, you have to take into account a generation gap. Workplaces were a lot different 30+ years ago in his formative years. IT was also very different 30 years ago.

I've only seen the promotion culture in the military be replicated by sales people doing sales-y stuff. In those worlds, which are sometimes MLM (multi level marketing), there is constant hype to keep you motivated. In the civilian world, no one wants you to get promoted, or get motivated enough to do a good job. They want you making widgets, answering the phone, closing tickets, etc. They want the leaves on the org chart to do the leafy stuff, so the branches and trunks can go play golf. Problems get fired, and if you shine too bright, you're the problem. Even if it's for no other reason that jealousy of your peers that causes people to complain about you.

Don't overlook the part where the boss can't understand or doesn't care that you're doing a good/above average/excellent job. In the business world, it is an accepted standard to put the employee in a position of disadvantage, for example by under paying or under training them. To the stereotypical middle manager and the bean counter, no one is competent anyways, so why waste money on training so they can leave the company?

Speed of Promotions

A year in the civilian world is about enough time to get your foot in the door and get your bearings. A year in the military world is 1/3 of your stay at any particular base. It's like people-years vs dog-years. Therefore, the speed of a promotion is vastly different.

In the civilian world, most promotions in small businesses are into management (most companies are small businesses), and I'd hazard a guess that's what most people have for a mental model of a promotion: "YES, now I can have minions!". It's not until you get into a bigger company with a lot of organization and/or a technical company that you will encounter things like pay grades such as "Programmer I, Programmer II; Engineer I, Engineer II; Senior Associate, etc".

Getting a promotion is a much bigger deal compared to the military, where you got 3 - 5 promotions in your first contract if you weren't a turdburgler. On paper, that's halfway up the ladder. In the civilian world, it will depend heavily on the size of the organization, but you probably can't expect more than 3 promotions if you stayed at a company for 20 years. That's a total SWAG (Scientific Wild A** Guess) by the way.

Most common advice in the civilian world

Most advice here on this SE boils down to one thing: go find a better job with better pay and less drama.

But you're a loyal, hardworking soldier who wants to improve and make the company better! Doesn't matter. The workforce is churning regardless of your loyalty or dedication, so companies can't/won't/don't invest in people any more than they are forced to. Useless sycophants run middle management, and they can find some other schmuck easy as pie; they won't care about turnover unless they are told to. Some industries "just have high turnover" and therefore no one cares about it.

The average stay at a company isn't terribly long. I recall reading that it was ~1.5 years, but that might have tech jobs I was looking up at the time. In general, it seems that the average is ~4 years. However, this Forbes article explains why people don't move up: they move out. The important part is the headline: Employees Who Stay In Companies Longer Than Two Years Get Paid 50% Less. Companies don't pay people to stick around.

Forbes gives us another good article with a story about how being a good soldier earned a long time employee condolences when he should have been congratulated.

Final points

Not only are the civilian and business world alien compared to the military world, but the way people think and react might as well be alien, like little-green-men alien.

People only care for #1 and will run away from anything that looks complicated, difficult, violent, dirty, or otherwise undesirable. Or associating with the same.

Just as they are alien to you, you are alien to them. You might be one of those crazy vets that might go postal on the office.

Esprit de corps sounds like some random foreign words to a civilian.

But they know everything about the weather, every game that played last night in every sport, and will eject themselves from any sort of conversation where all parties are not in 100% disagreement (can't have any conflict, remember?).

Source: Personal experience and reflection.

  • I've upvoted because I think this is an important answer for helping generate understanding between civilians and former-military. – Aaron Sep 5 at 13:29

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