Microsoft small-business nightmare infrastructure norms?

July 9, 2009 9:42 AM

Is IT managment in most medium-size businesses (microsoft based, for the most part) normally like managing a cobbled-together series of workarounds on top of workarounds, tied together with bailing twine and gum? If so, is there any workable way to fix this?

I'm a contractor working at a business with approximately 150 workstations dispersed over several physical locations in several states. While things have greatly improved since I started here a few years ago, for the most part I constantly feel like I'm only catching up to problems after they occur. There is no formal IT budget, no IT group, no policies (except for my own documentation), etc. I manage everything that blinks or hums, and I report to one individual at the company.

Almost everything I deal with is a workaround implemented years ago. The single thing that I feel is efficient is a new Linux web server and web application that I was solely responsible for. Everything else is a series of taped-together "solutions."

Is it normal for a business of this size to, first of all, be in this position, and second of all, to apparently not care that they are? How can I change this?

Every time I attempt to instigate some kind of reform it's met with hostility due to budgetary concerns (i.e., "We should really audit our OS software and buy XP licenses for any workstations using pirated software. Mr. Smith should be told not to bring pirated copies of Office and install it on the computers."). There are dozens of legacy applications running on hardware for which replacements are only available on eBay. There are business-critical applications running on Windows 98 workstations for which there is no re-install media, no documentation. There is no policy of retiring workstations or upgrading them. Everything is MacGuyver'ed into a semi-functional state.

Some applications are delivered over a Citrix farm but they have no relationship with Citrix vendors and aren't willing to pay for training on Citrix management. As a result managing the farm is mostly a cross-my-fingers kind of thing. To be fair to Citrix, apparently their software is designed to be a nightmare on purpose.

In the central office we have multiple versions of Windows server running various things in a cobbled-together fashion. We're only just now discussing disaster recovery, which I expect to go badly because it's going to cost at least $50k if they want to do it properly.

There is no concept of the recurring costs of software or hardware upgrades. If it's running today, there is no desire to explore whether it should be upgraded. There is, however, an expectation that things should never fail. Ever. All services should always be available. This company actually has very large customers which you've heard of. I don't want to even discuss PCI DSS compliance.

Is this normal for small Microsoft-based businesses? Almost all of the reforms I'd like to implement are seen as painful or undesirable due to the fact there is a non-zero cost both in time and money, or because they would inevitably cause problems (like how we're using a non-private subnet 192.100.100.0/24 internally because nobody knew what the hell they were doing.) or would cause a change in the way people get their work done and send some employees into fits of screaming rage. Ask me how I know!

How do you connect these types of decisions to their end-result: malware infections requiring multiple days to clean up, regular travel expenses to visit remote sites to fix problems that otherwise wouldn't have occurred, old hardware dying and taking down business-critical devices that I didn't even know existed, etc.? This is seen as a normal cost of doing business to them. I find it difficult to quantify such inevitabilities on a monetary scale because of their chaotic nature, but any discussion is immediately rejected as an expense they just can't afford.

posted by odinsdream to computers & internet (26 comments total)

You've answered your own question, really: You need to compare the expense of doing things right with the REAL cost, and risk of cost, of doing them half-assed.

Take a two-step approach to the situation.
Part One: You can gather some rough numbers of man-hours lost, sales lost, productivity lost, due to specific incidents that have already occurred, and compare that number to the cost of the specific planned professional solution that would have prevented the incident.
Part Two: Take each of the various shortcomings you have identified. Create a realistic budget for bringing that specific item up to spec. Then figure a reasonable bad-case scenario of what could go wrong if the correction is not made, including lost sales, and diminished productivity. You should have no trouble finding real-life sources for your disaster estimates as the internet is rife with real stories of companies staggered by preventable IT disasters.

Out of your account of your company's IT shortcomings, the pirated software thing sticks out the most, to me. If they are reported to or otherwise audited by MS, Adobe, or other major vendors, they could wind up SCREWED. I know of one company that was fined $1M because they could not prove they paid for the software in use by their employers. One Meeeliyon Dollars. Properly managed IT is not an expense, it's an INVESTMENT, and you need to find one sympathetic soul in senior management you can convince of this philosophy, and work through him to save the company from itself.
posted by BigLankyBastard at 10:03 AM on July 9 [1 favorite]

I find it difficult to quantify such inevitabilities on a monetary scale because of their chaotic nature, but any discussion is immediately rejected as an expense they just can't afford.

Just do what everyone else does. Make up numbers. Or rather, you know about past failures, it's certainly valid to extrapolate into the future, for this.
posted by smackfu at 10:10 AM on July 9

Is this normal for small Microsoft-based businesses?

I've heard a lot of horror stories from my husband, who was an IT consultant to small businesses for many years. Sounds pretty normal to me.
posted by desjardins at 10:26 AM on July 9

The answer to your main question is a resounding yes. It's easy to overlook IT (and many other kinds of infrastructure) if the management thinks that (1) it's working well enough and (2) it's a huge outlay of cash they don't have. There are a few different lines of argument you can try to convince your bosses to cough up some resources. Some of these will work better than others. The key is to try to think about it from their perspective. Imagine that they're really, really cash-poor right now (they probably are). Imagine that they're having trouble making payroll (they probably are). Imagine that they have no room to make long-term decisions, because the short-term is about to come crashing down around their ears (it probably is). Then think about how these arguments will sound to them.

(1) "This is industry standard and/or a legal requirement." This argument probably won't work. What do your they care? What they're doing now has worked fine for them so far, so why should they plop down 50k to fix a problem they don't even see?

(2) "If we spend the resources to build it properly now, you'll save lots of money in the future." This argument probably won't work. Why should they pay lots of money now without any guarantee of future benefits? It's just a gamble, and not a good one. What's the guarantee that they won't have to pay more money later to fix the expensive system you just bought? And even if the expensive system does work, how will you be able to prove that they've saved anything?

(3) "This will help bring in more revenue and/or reduce costs right now." Ding ding ding! This is the only argument they're likely to listen to, because you're solving a problem that's hurting them right now. Try to tie your preventative measures to immediate solutions.

Here are some general things I'd recommend to help you make your case.

- Develop allies. If you can find one or two managers who will advocate for you, that'll help.
- Put the spotlight on costs when they happen. If something breaks, do you spend all night trying to fix it so it'll be back up in the morning and nobody will notice it even went down? Don't do that. If you do, no one will believe you later when you say that IT problems are costing the company. Do your job, solve the problems, but don't go out of your way to hide them. Bring problems to your bosses' attention while they're happening, not long afterwards.
- Start keeping a log of IT problems and costs. This will help you make a concrete case if you're called upon to do so.

But truly, the most important thing is for you to link each of your proposals to revenue or immediate cost reduction. The more you can do this, the more you'll earn yourself brownie points for future use. "I've saved you 15k on transaction costs in the last 9 months -- that more than covers the cost of Improvement X. And the great thing is that, once Improvement X is in place, it'll save you an additional 30k over the next 12 months."
posted by ourobouros at 10:49 AM on July 9 [6 favorites]

Wow I feel a lot better about my job now, thanks. There are better places to work where you might have less stress.
posted by jockc at 10:53 AM on July 9

The only way you'll get anything done is to quantify what the status quo is costing them, even if it is chaotic or unknowable. If you identify what the "fix-as-it-breaks" cost is for the next 3-5 years, then show how your decently detailed plan to fix all or part of the problems will cost less, you will have a better chance of getting minds changed. If the push-back you're getting is money, talk to decision makers about money (not problems).
posted by Pants! at 10:54 AM on July 9

I walked in to a place like that a few years ago - stayed for 2 years and left. Huge headache. The cabling, computers, software, - everything was patched together. It was a long two years getting everything up to normal standards. This kind of job will age you very fast.
posted by jaythebull at 11:17 AM on July 9

I don't think it's fair to correlate the mess with the fact that the place is a Microsoft-centric IT shop. My personal experience leads me to believe that this type of issue comes up in small business that have their IT department consist of one person. Usually, as long as things "work" when the boss needs it to work, the IT guy operates without supervision, and does whatever he wants, however he wants to do it.

To emphasize what ouroburos said, I think the only way you'll be able to change your boss' mind is if you show some immediate financial benefit as a result of the changes you're proposing. Trying to explain to the boss that your suggestions will make the system more reliable/stable/resilient without showing him how it's going to keep more money in his pocket will most likely result in failure.
posted by vall at 11:22 AM on July 9

What you describe is entirely within the norm, and the advice above is great, I would just add that you need to look at things quarterly or yearly and summarize how much the lack of investment in both time and resources is costing the business.

You're really going to have to spend some amount of effort to find a politically workable way to tie the folks denying the investments in better infrastructure to the outages experienced.

The first step of this is to start out with process and standards. Make sure that every time there is an outage that impacts some volume of users, some site, some application you do a Post Incident Report (PIR). Make sure that directors/vp's/etc get the PIR's and that when it happens again and everyone is mad as hell you can point at the PIR that articulated the issue last time it happened and the recommended mitigation strategies.

Start small, get traction in one highly visible area and make sure that people associate something not breaking with the time and effort put in to make sure it doesn't fall over...the web server you installed is a great example.
posted by iamabot at 11:24 AM on July 9

I agree that this sounds pretty normal, though horrifying.

I had decent luck presenting similar cases to my non-IT bosses by making super-simple, obvious graphs of "Cost to Fix Now" vs. "Cost if it Fails". So, picture two vertical bars on a chart, one very short and the other quite large (to scale and backed up by real numbers, of course). You can add a couple convincing bullet points like "10 business days downtime" or "80% chance of failure in next 12 months" next to the "if-it-breaks" bar, but keep it super concise. Basically, do what BigLankyBastard recommended, but assume that you have approximately 20 seconds to make your case in the materials you prepare. Graphs showing major differences will grab their attention much better than a long list of numbers. Be ready with a breakdown of the costs, risks, and impact of failure on the business on a separate page, if they ask for details, but start with the chart.

Also, when you're presenting these things, prioritize what needs to be fixed. Management seems to stop listening pretty quickly when you refuse to acknowledge the financial realities of business. If you insist that everything needs fixing, nothing will get approved for fixing, because the money just isn't there. It doesn't matter how much it might cost to fix later, it's still cheaper than how much it certainly costs to fix now.

Instead, go in and state that (A) there are a lot of potentially expensive ticking time bombs laying around ("I've put together a list, let me know if you'd like to see a copy"), but also (B) you understand that financial constraints won't allow the company to fix all of them, so (C) you've done your best to prioritize the issues and only want to talk right now about 2 of them. Then you can present these 2 issues with your attention-grabbing graphs. You might even try an approach like, "Issue #1 would be the cheapest to fix, and would be a great starting point. On the other hand, Issue #2 is more likely to fail and will cause more disastrous results if it does. I'm not sure how you want to prioritize these things, but we really need to start somewhere."

Good luck! I applaud you for having the courage and determination to even try to sort out the kludges!
posted by vytae at 11:37 AM on July 9 [5 favorites]

Mostly things there are not going to change, I have worked in atmospheres like that, and the problems come from up top. It's all about cost cutting nowadays, which is tolerable if you have good practices and framework in place and not tolerable in situations like yours.

First things first: the conversation about pirated software? Have the conversation again, over email, where you are asking to be legitimately licensed and they say no. Export that piece of mail and save it to a thumb drive that you leave at your house, forward it to your gmail account, and print it out and leave it at your house too. If they do get audited, they will blame you - I have seen too many instances where the sysadmin got fired after an ugly software audit - and you need proof that you were not the one driving that particular bus.

Other than the current widespread panic about money, people run businesses they way they are because they have no vision and regard IT as purely an expense, not something that has a cost but also a benefit in terms of dollars. To talk to them, you need to learn their language - learn some completely annoying management-speak and talk to them about the 10,000 and 50,000 foot view, the 3 and 5 year plans, and break it down to dollars. Talk to them about auditing your hardware and software in regard to how their ennui is costing them money and personhours. (Low level example: a couple of jobs ago when I was doing desktop support, I finally got the bosses to implement and enforce end-user compliance agreements after I showed them, over a course of months, how many dozens of hours my coworker and I spent cleaning spyware off of company computers. Since we were a 2 person department, they knew we had plenty of other, more critical work to do but were pissing around scrubbing the same workstations over and over again because people were playing poker or whatever at work.)

Not to be a giant bummer, but I want to reinterate my first comment: it will change very little. There will be a lot of frustration and head-banging-on-keyboard moments for you to enact the little change you will manage to hammer onto them. Do what you can, learn as much as you can, bide your time and when things look shinier out in the world start job hunting.

Good luck.
posted by 8dot3 at 11:45 AM on July 9

This is not Microsoft related. They're having problems because they don't see IT as a particularly valuable part of their organization. They ARE going to have a rude awakening. If it was purely a budget issue, they could have switched to free/open source products long ago.

What they lack is leadership and vision, and that is something that needs to come from the top, not the bottom.

Do your best to transition them to free solutions, but don't expect anything to change. LOOK FOR ALTERNATIVE EMPLOYEMENT OPTIONS.
posted by blue_beetle at 11:46 AM on July 9

I don't think it's fair to correlate the mess with the fact that the place is a Microsoft-centric IT shop.

I've restrained myself from the rants I could make that are solely the result of MS-based software. The amount of crazy those folks can pack into software is astounding. Let's check uptime on apache... 155 days. It would be over a year if it weren't for my dolt manager who unplugged it thinking it was the blue-screened Exchange server.

My main beef with the MS infrastructure is the associated costs of everything else. If I want to do some complex volume management or clustering, that's prohibitively expensive because I have to get MS licenses for clustering, different MS database products, third-party utilities that also have licensing costs, etc. Backup strategies on Windows require third-party software to be even marginally useful. Open-source software for some crazy reason includes the capability to do complex backups without extra software.

Windows alone isn't the problem, it's what it forces them into if they want to do anything useful at all. Combine this with the infuriating madness of malware, desktop environments that let the user do things that should never make sense in the first place, IIS being a complete joke, etc. and it just ends up leaving an acrid taste to me.
posted by odinsdream at 12:03 PM on July 9

Yes, it's normal. It gets that way because companies grow, and their needs grow, in ways that, generally, that never quite seem to conform to the plans and estimates. Budgets are always a consideration, so IT is usually always playing catch-up with actual needs.

Add to this things like 1) The off-the-shelf solutions not quite providing what's needed...or being complete overkill, a 2) The inevitable arrival of an IT manager who has his own pet ways of doing things.

So...yeah...what you're experiencing is perfectly normal.
posted by Thorzdad at 12:05 PM on July 9

Sorry you're having to manage such a mess.
In addition to the many suggestions above, I'd add this one:
develop a Risk Register, which shows, in no uncertain terms risks for failure (of say, the Win98 workstations) in term of (1) Likelihood of occurrence (expressed in %, over the next 6 months), (2) Severity (expressed in business terms - but also in terms of "work station fails, no recovery possible, data/work lost), and (3) Priority - this is about how important that Win98 workstation is to the overall scheme of things.
You'll probably need help, but it should help bolster your case, especially if you can attach those lost dollars/opportunity costs to it.
Good luck.
posted by dbmcd at 12:14 PM on July 9

Hmm I am a network admin of a library and was a network admin of a regional nyc insurance company. Both networks where not cobled together.

Any network that is cobled together means the person did not do the job right .

The amount of management software that microsoft provides is astounding.

Have you tried using microsoft virtual pc and things like that to at least virtualise this windows software?

Have you tried programs like avast for virus scan which are free?

Make sure you are also running wsus which is also free.

Try using microsoft system state which is free too.

Make sure every xp system is running windows defender (free again).

You can use pfsense for a firewall between the network and the internet(free also)
.

Also for disaster recovery look into a program called ultrabac. IT does full server based imaging with windows pe recovery cds and is cheaper then a lot of options.Windows 2003 includes tape backup software and windows 2008 includes full server image backup


Dont blame it on microsft. Microsoft provides many free software programs to help you . If you want i can give you some tips if you pm me.
posted by majortom1981 at 12:17 PM on July 9

Ps i suggest highly also installing spiceworks. This will help you a lot to get a handle on what is on the network and help you prioritize things. Its also free.
posted by majortom1981 at 12:19 PM on July 9

Not only is IT just seen as an expense and a liability, that everything you do costs them money and detracts from the revenue, but most people have only a vague notion of how computers work. This leads you talking in metaphors and analogies to management ("integrated sysems"/"SOA"/etc.) about systems that cannot be reduced to simple metaphors. It is very, very hard to show ROI on moving to new system or hiring a $80k Ruby on Rails programmer to create a proper approach to dealing with the problem.

I think fundamentally there is no way around this until IT people start moving up into upper management in smaller and mid-level companies that are not IT focused. Right now there is a definite IT ceiling that's not helped by the fact that systems get more efficient, IT does more, but the number in the department shrinks.

But I've been sort of successful in increasing my own budget and forcing management to do what is right:

(1) Record, record, record. Since it is only you, you only have your documentation and you probably don't write everything down. You should really record everything. Every time someone calls you, every time you do a Citrix update, every time you spend 6 hours doing something because it is on Win2k when a Win2k3 license and a $2500 server can solve the problem. Make sure you're really detailed and set aside time each week and try to organize the data. You will find yourself beginning to organize this data in a more meaningful way that you can now report on. For example:

- People in my organization are of low technical ability and will often download spyware and shit, but at the same time it is nearly impossible to have a locked down desktop where nothing is installed, nor is it possible for me to remote in and install it for them. If someone is at a vendor or client site and they want them to install some stupid conferencing app they will only use once, well it looks bad if they say "I can't without my administrator." The solution was simple, I went back in my logs, looked at all the times in the past year I spent cleaning things up, or was called to provide a password and came up with a solution. Users would be given VMWare ACE workstations on their laptops, which would have an up to date base image of the software they needed. I taught them how to roll back snapshots and if anything went awry to simply roll back and they'd be good to go. I had well documented the number of hours spent on the problems previously, the price of the software, and the cost to the company if you assumed that me and employee x working at hourly rate of $y* was far less than this solution. It has been working great far.

* Most likely you won't have access to salary information, a good way to go about this is finish the report, tell HR what you're trying to do and have them compute the dollars and pass it on to the president or whoever.

(2) Mockups really, really help. For example, I was being asked for what was essentially an executive dashboard, but was being communicated to me as "reports" and other things that didn't sound like an executive dashboard. I had been drumming the beat to getting off our old accounting system and onto something more modern. I was able to hack together a simple ASP.NET web site that took the mangled accounting data, mashed it with some other Excel documents that were floating around and produced a nice Google Map with our vendors and the age of the invoice as a color (so 90 days plus was red, etc.). Sure you could dig around in the accounting software and produce an ugly Crystal Reports but it wasn't nice and didn't tie into some "custom software" (the Excel workbooks). Obviously I wouldn't want to run a production system of Excel workbooks and a hacked together API, but they actually saw what I was talking about and how once you free data you can throw together in all kinds of neat ways. As an added bonus I made a script that sent an SMS (really an email to [e-mail]) to the CFO if an invoice had aged to a certain level AND the D&B number (credit rating) was low or falling. This absolutely delighted him and I was able to show that including IT in policy meetings and on emails was probably a good thing to do and now I can present large budget projects without being laughed at or having my eyes rolled at like I'm 250 pounds and wearing a Star Wars t-shirt. Consequently I get more respect and freedom.

It is not one thing, but a lot of little things and if you get caught up with what is wrong and how it is obvious things should be fixed for a big price, you're not going to get very far. I would start out small, and with the pirated software first. Don't make a huge deal that looks like you're going to rat out the company. Simply conduct a thorough audit of your systems, identify the software being pirated and the cost for replacement. Also identify cost savings where you can uninstall it and put on a less expensive alternative. Adobe Acrobat Pro comes to mind as something people say they always need but really only need to convert office documents to PDF which 2007 does natively if you pay for it. Make it a 6-9 mo. roadmap to compliance and make clear in no uncertain terms that if you don't get budget to get licenses for software packages you'll begin to uninstall and replace with free alternatives when available. At the very least if you do get a BSA audit in the meantime at least you can show you had a plan in place and were actively trying to fix your compliance problems. They're not completely unreasonable people and if you show you got caught up XP licenses in July and were looking to do the same with Office licenses in August (with a paper trail!), they'd rather you pay for their software than have to take you to court.

Sorry IT really sucks some days because you just don't get any respect, but on the other hand your business runs because of you. Do not sit passively by and make the trains run on time. Do a little self-promotion and show that you're not just installing programs and running tape backups, that the choices you make really do effect revenues and costs. You absolutely do not want to be in the position of upper management not recognizing the difference between you and the kid down the street who is really good at fixing computers. Hope that helps?
posted by geoff. at 12:47 PM on July 9 [1 favorite]

I'd say it's somewhat common but I blame IT management as much as executive management. It's not unreasonable for a company to try and keep costs down. Unfortunately many IT types live in their own little world and may have little to no curiosity or knowledge of the business they're in. As a result, they can't communicate the costs, benefits, and reason for an expenditure in a clear manner.

From executive mgmt perspective:
- they've been burned by IT projects that did not work as promised
- they've been burned by projects that just didn't work, result in excessive downtime.
- they hear complaints from employees anytime anything changes, whether the changes are positive or not. They rarely hear anything quantitative from IT about the results of the changes.
- they've been burned by IT requesting funds for something, then coming back and requesting more because the manager did understand of all the costs involved.
- they see no real ROI because nobody has explained it
- finally, the status quo might actually be the best business decision. You have limited resources, may be laying people off, is $50k for disaster recovery the best use of resources right now?

How to fix it? ITIL is your friend. Believe it or not, getting to that last point, where an actual business decision is made to keep the status quo, is a victory of sorts. It means you and your mgmt team have a clear understanding of systems, costs, where your time is spent, etc. ITIL looks overwhelming but you don't need a ton of resources to implement it (and you don't need to implement all of it). When you have a decent handle on things, re-read vytae's post before you go to mgmt.

Every time I attempt to instigate some kind of reform it's met with hostility due to budgetary concerns.
Who do you report to? Is it the CFO or Ops Manager, etc. or is it an IT person? Is it hostility or is it just "we can't do it?"

You absolutely do not want to be in the position of upper management not recognizing the difference between you and the kid down the street who is really good at fixing computers.
Fantastic advice.
posted by txvtchick at 12:54 PM on July 9 [1 favorite]

Any network that is cobled together means the person did not do the job right .

In my experience networks change the least and are the most formally defined part of any IT system, so usually they're not cobbled together. The systems that are directly part of business processes are the worst offenders as they change a lot year to year and even client to client. There's no way to formalize processes at small to mid size company where HR might really be just one person. We often hire people from large companies who bemoan the fact that they used to be able to sit down at any desk and have everything well defined. You could pop out any mid-level manager or even maybe a step above, plop someone down and they could be trained on "the system." The economics of creating that for a smaller company are just not there. In my opinion this is why smaller companies, especially professional service companies, are able to compete with large entities on an overhead basis. As anyone who has had experience implementing Oracle or SAP can tell you, it is not a bed of roses the other away around.
posted by geoff. at 12:55 PM on July 9

Who do you report to? Is it the CFO or Ops Manager, etc. or is it an IT person? Is it hostility or is it just "we can't do it?"

COO, technically. It's a small company that has bought other small companies, and is now a medium-sized company with the same amount of management staff. Two people are in charge of the decisions that would affect my department, one of whom is the president. They are both technically savvy individuals and are excited about projects, but appear to prefer to cobble solutions together without planning for the future. This seems to be a personality issue, not limited to the IT infrastructure alone.
posted by odinsdream at 1:20 PM on July 9

What I mean is, they will evaluate a complex solution that would benefit them long-term, but then take the position of "Or, we could save all that money by going to the attic and pulling down that old server.. then we could use this crap over here... and then we could get Phil to write some ODBC driver so we don't have to buy the connector...and let's not ask anyone who will use this what they think it should do..."
posted by odinsdream at 1:23 PM on July 9

"Or, we could save all that money by going to the attic and pulling down that old server.. then we could use this crap over here... and then we could get Phil to write some ODBC driver so we don't have to buy the connector...and let's not ask anyone who will use this what they think it should do..."

Right and unless you can track and record that after that the ODBC driver cost x hours of downtime or you spent x hours trying to make it work and can present that in a report you can never justify the ROI. You might be surprised to find that it only cost the company $1,200 in direct hours lost a year when the connector costs $7,500. The point being is that the least optimal solution from an engineering perspective might be the best for the company's financial health but there's no way to say one way or the other without tracking costs and pinning it to an expense on the balance sheet.

Of course if you can't get Phil on board with this you have deeper organizational problems, but I've found people are always usually very willing to track not only their time but document what they do because it proves they are doing something and are useful. I've never met resistance when I've asked people to shoot me an email everytime something goes down or they get frusterated or they have to spend time hacking up an Excel spreadsheet.
posted by geoff. at 1:58 PM on July 9

To answer your primary question,.. I would say "YES"...I'd be willing to bet that "cobbled together" would be a applicable label for most small to medium business IT departments. I think it comes from a variety of factors:

1.) IT Staff turnover happens frequently. Each batch of employees has personality/preferences about the "best" way to do something. Also, "putting out fires" is stressed more than documentation,.. so you get into this circular trap of nobody ever taking the time to organize, update and document things. I agree with the ITIL suggestion above.

2.) In all the years I've been doing IT Support/consulting... I would say the hardest issue BY FAR ABOVE anything else, is breaking a company out of the habit of choosing the cheapest solution. Seriously. Changing that mindset is so frustratingly difficult sometimes it made me want to scream. But you have to be persistent (take the advice above about creating charts comparing "cost to fix now" to "cost to repair the bigger mess later".)

3.) Management doesnt understand the "boots on the ground" reality of how badly cheap decisions effect the day to day productivity of employees. (because management is often several layers of bureaucracy above, and they are simply out of touch with how frustrating it is for the average office worker to struggle with an old Pentium3 with only 128meg of ram and a unreliable network connection). I'm not saying this to belittle management positions -- BUT, have you ever worked in an office environment where the CEO's computer was the oldest/worst of the bunch?... No?.. yeah, thats what I thought. Human beings tend to have narrow vision and only really care about the things that effect them directly. Any CEO or CIO worth his salt should have a fairly up to date Asset Management report -AND- an active plan to replace/upgrade the worst computers in the company. Yes, I know, budgets are tight - but IT infrastructure has become as important as power and water. Any company that doesnt treat IT as a critical core element is doing themselves a huge disservice.


4.) When you are in a project attempting to transition a shoddy IT department into one that actually works - your most difficult task (but also can be your best ally) are the end users (not just at the bottom of the company pyramid, but computer users at all levels). Here is why:

..............If you keep them in the dark about upcoming policies,.. if you dont re-train them.. if you "surprise" them with new approaches... they will fight you every step of the way, find ways to circumvent the environment and basically make the project difficult (if not a complete failure) Because they'll think: "oh great, here's another change to our systems that will probably make things worse, again.."

..........If on the other hand, you introduce upcoming changes in a positive light, provide some training sessions, explain why the new way is more beneficial than the old way,etc... you can get everyone on board and the project will be easier. You have to find a way to create the mindset where they cant wait to use the new system because its going to be so much better. (bonus points if you can hear rumors about employees telling other employees things like: "oh man, did you hear the new system will let us do X, Y AND Z ?!?!?.. its gonna be awesome")

Part of the skill of being a great IT person is not forcing change because you know better, its being a good leader and finding positive ways/examples to show a better path. I know, thats hard when stress is high and you'd much rather be the BFOH.
posted by jmnugent at 2:08 PM on July 9 [1 favorite]

Two people are in charge of the decisions that would affect my department, one of whom is the president. They are both technically savvy individuals and are excited about projects, but appear to prefer to cobble solutions together without planning for the future.

I wonder if it's possible for you to negotiate more responsibility and autonomy. Are they good people? Do you like them? Would you want to work as a regular employee in a mgmt position for them? You would need to get your ducks in a row first as discussed upstream, and also internalize this:

...You might be surprised to find that it only cost the company $1,200 in direct hours lost a year when the connector costs $7,500.

That said, it sounds like you could really do them some good. At some point as they grow the company they will need some people who can bring a little order to all the creative chaos. They are enthusiastic about projects, that's great. Maybe they can realize there's other stuff they can be doing with their time, if you can grow and work within certain constraints. If they don't have that capacity for delegation then it's probably time to move on. But try learning and demonstrating the business point of view first.

Also jmnugent is right on about communicating to the end users. It really does help. On that note: SANS has a bunch of policies and end user communication stuff. I like the "Don't be Dan" (word doc) poster.

BUT, have you ever worked in an office environment where the CEO's computer was the oldest/worst of the bunch?

I have. He went to a lot of effort to set a good fiscal example - no private jets at that company. Awesome guy, and the company was far more profitable than any other that I've worked for. YAY for profit sharing.
posted by txvtchick at 3:38 PM on July 9 [1 favorite]

Based on the experiences of others as well as my own meager experience, the answer to the first question is definitely yes, and to the second, likely no:

The Daily WTF

Coding Horror

Softpanorama IT Slacker Society Manifest

More subtle insight here:

Why a career in computer programming sucks
"Real managers, who usually don’t understand anything about computer programming but who don’t like the idea that they have to pay high salaries to a bunch of people from foreign countries, love the reports presented by project managers, because the reports create the illusion that progress is happening and that the money being spent on the IT project is not being wasted."

How Boomers and Generation-Xers brought about the dumbing down of Information Technology (IT)

Mendacity and the IT Company

One Half A Manifesto, by Jaron Lanier
"If anything, there's a reverse Moore's Law observable in software: As processors become faster and memory becomes cheaper, software becomes correspondingly slower and more bloated, using up all available resources" (cf. Jevon's Paradox)
posted by renovatio1 at 10:58 PM on July 10