IT inferno: The nine circles of IT hell

Spend enough time in the tech industry, and you’ll eventually find yourself in IT hell — one not unlike the underworld described by Dante in his “Divine Comedy.”

But here, in the data centers, conference rooms, and cubicles, the IT version of this inferno is no allegory. It is a very real test of every IT pro’s sanity and soul.

How many of us have been abandoned by our vendors to IT limbo, only to find ourselves falling victim to app dev anger when in-house developers are asked to pick up the slack? How often has stakeholder gluttony or lust for the latest and greatest left us burned on a key initiative? How many times must we be kneecapped by corporate greed, accused of heresy for arguing for (or against) things like open source? Certainly too many of us have been victimized by the denizens of fraud, vendor violence, and tech-pro treachery.

Thankfully, as in Dante’s poetic universe, there are ways to escape the nine circles of IT hell. But IT pro beware: You may have to face your own devils to do it.

Shall we descend?

1st circle of IT hell: Limbo
Description: A pitiful morass where nothing ever gets done and change is impossible
People you meet there:Users stranded by vendors, departments shackled by software lock-in, organizations held hostage by wayward developers

There are many ways to fall into IT Limbo: When problems arise and the vendors start pointing fingers at each other; when you’re locked into crappy software with no relief in sight; when your programmers leave you stranded with nothing to do but start over from scratch.

You know you’re in Limbo when “the software guys are saying the problem is in hardware and the hardware guys are saying the problem is in software,” says Dermot Williams, managing director of Threatscape, an IT security firm based in Dublin, Ireland. “Spend eternity in this circle and you will find that, yes, it is possible for nobody to be at fault and everyone to be at fault at the same time.”

A similar thing happens when apps vendors blame the OS, and OS vendors blame the apps guys, says Bill Roth, executive vice president at data management firm LogLogic. “Oracle says it’s Red Hat’s fault, while Red Hat blames Oracle,” he says. “It’s just bad IT support on both sides.”

Michael Kaiser-Nyman, CEO of Impact Dialing, maker of autodialing software, says he used to work for a nonprofit that was locked into a donor management platform from hell.

“The software took forever to run, it only worked on Internet Explorer, it crashed several times a day, and was horribly difficult to use,” he says. “The only thing worse than using it was knowing that, just before I joined the organization, they had signed a five-year licensing agreement for the software. I wanted to kill whoever had signed it.”

Organizations also find themselves in Limbo when their developers fail to adopt standard methodologies or document their procedures, says Steven A. Lowe, CEO of Innovator LLC, a consulting and custom software development firm.

“Every project is an ordeal because they’ve made it nearly impossible to learn from experience and grow more efficient,” he says. “They spend most of their time running around in circles, tripping over deadlines, yelling at each other, and cursing their tools.”

How to escape: “When you’re digging a hole in hell, the first thing to do is stop digging and climb your way out,” says Roth. That means making sure you have the tech expertise in house to solve your own problems, going with open source to avoid vendor lock-in, and taking the time to refactor your code so you can be more efficient the next time around.

2nd circle of IT hell: Tech lust
Description: A deep cavern filled with mountains of discarded gadgets, with Golem-like creatures scrambling to reach the shiny new ones at the top
People you meet there: Just about everybody at some point

The circle of tech lust touches virtually every area of an organization. Developers who abandon serviceable tools in favor of the latest and greatest without first taking the time to understand these new frameworks and methodologies (like node.js or Scrum), thereby preventing anything from ever getting done. Managers who want hot new gizmos (like the iPad) and invent a reason why they must have them, regardless of the impact on the IT organization. Executives who become fixated on concepts they barely understand (like the cloud) and throw all of an organization’s resources behind it in the fear of falling behind the competition.

“In reality, we all visit the circle of lust now and then,” says Lowe. “The problem with tech lust is the accumulation of things. You can get so mired in ‘we can’t finish this project because a new tool just came out and we’re starting all over with it’ that nothing ever gets done.”

How to escape: It is difficult to break free from the circle of tech lust, admits Lowe. “We all love shiny new things,” he says. “But you have to know what’s good enough to get the job done, and learn how to be happy with what you have.”

3rd circle of IT hell: Stakeholder gluttony
Description: A fetid quagmire filled with insatiable business users who demand more and more features, no matter the cost
People you meet there: Demons from sales and marketing, finance, and administration

This circle is painfully familiar to anyone who’s ever attempted to develop a business application, says Threatscape’s Dermot Williams.

“By the end of the project, the specifications, budget, and timescale of the project bear no resemblance to the ones you began with, thanks to users who keep adding in ‘just one more thing we should have thought of,'” says Williams. “A developer who has the misfortune to land in this circle will never actually reach the nirvana of being ‘feature complete’ because the specification itself is never entirely finalized.”

How to escape: There is only one way out, and it entails confronting the demons with some hard realities, says Williams. “Escape from this circle is best effected by wielding the magic mirror of painful truth,” he says. “This powerful weapon makes the demons look into their own dark hearts and realize that ultimately it is they who have most to lose from feature creep.”

4th circle of IT hell: Corporate greed
Description: An acrid forge where piteous creatures drown in a river of molten gold
People you meet there: Corporate executives and shareholders. Also: Donald Trump

This circle is filled with those who put personal financial gain ahead of the needs of customers, says Anthony R. Howard, author of The Invisible Enemy: Black Fox and a technology consultant for Fortune 50 companies and the U.S. military.

About three years ago, Howard was consulting for a brand-name hardware maker when he was asked to design a new server for one of its clients, a major search engine. Howard’s design was cheaper and cost less to operate than the servers the search engine was currently using. The customer was ecstatic and ordered $20 million worth. The problem? It would take eight weeks to build, or several weeks past the end of the manufacturer’s sales quarter.

“The manufacturer wanted to report that $20 million sale to Wall Street, and it couldn’t,” Howard says. “So I was placed under tremendous pressure to convince the search engine guys to forget the new design and buy something we already had.”

In the end, however, Howard says he persuaded the manufacturer to accept a smaller purchase order for its current machines to fulfill the search engine’s immediate needs, with the promise of a larger commitment to the new design down the road.

“When IT architects are working projects that will bring in tens of millions of dollars, the folks in the ivory tower want that revenue ASAP so they can present it to Wall Street — and collect their bonuses,” he says. “At the same time, customers want everything, including products that don’t exist yet. It’s a double hell.”

How to escape: Political savvy, dedication to the customer, and supportive management are the only ways out, says Howard. “Ultimately it’s always about the money,” he says. “You have to figure out how to deliver the results they want in some other way. But a lot of people just give into the pressure.”

5th circle of IT hell: App dev anger
Description: A fiery pit of smoke and brimstone, where geeks and suits alike grow hot under the collar
People you meet there: Programmers, developers, C-level executives

In the world of software development, deadlines are constant, pressure is intense, and tempers flare. When things go south, the inhabitants of this circle tend to scream first and ask questions later.

Larry Roshfeld, executive vice president at Sonatype, an open source governance solutions provider, says his team recently worked with a large financial institution to develop custom software for the bank’s commercial division. But when the bank’s legal team scanned the code, it found hundreds of potential copyright conflicts that would take weeks to resolve.

“The commercial banking team started screaming, ‘We need that app now,'” he says. “Another banking team got wind of it and started screaming, ‘We need you to work on our app now; stop wasting time on that other app.’ The legal team was screaming, ‘Nothing gets released until you clean up the license and copyright stuff.’ I heard swear words I had never heard before. People were literally foaming at the mouth as they yelled at each other. Last I heard they were all still at war over this.”

Brenda Christensen, now director of public relations for Nimble, a Web-based social CRM application, remembers sitting at a board meeting for a software vendor she worked for in the previous century when the company president began throwing objects at everyone else in the room.

“He was a programmer, liked to stay up all night, and didn’t care for our 10 a.m. meetings, so he was already surly,” she says. “When he found out we were late on a version of the software for Windows 95, he just exploded and started hurling anything within reach. After that, people never knew when he’d go off. It didn’t make the culture there very conducive to creative thought.”

How to escape: Eventually many hotheads will find themselves forced out of a job. Still, you can avoid most blow-ups by doing a better job of keeping everyone informed at every step of the way, says Roshfeld. “In our example, if the development team had licensing information at the early stages of development, they could have made more informed decisions and averted a crisis,” he says. “Learning of critical flaws late in the development process inevitably leads you down the path to the fifth circle.”

6th circle of IT hell: Tech-cult heresy
Description: An inscrutable labyrinth where all paths lead to the same destination, lit by the fires of nonbelievers burned at the stake
People you meet there: Apple/Microsoft/Google fanboys, Wikipedians, open sourcers, and any other member of an IT cult

Wherever true geek believers congregate, the rest of the world is cast into the pit of heresy. Open systems versus proprietary software, Apple versus Microsoft — it doesn’t matter what side you support, there’s always heresy on the other side, says David O’Berry, a strategic systems engineer for McAfee and liaison to the Trusted Computing Group, a vendor-neutral industry standards organization.

“People who use custom or commercial off-the-shelf software believe open source is heresy, while open sourcers believe closed systems are heretical,” he says. “The reality is that the business world has to leverage a mix of custom, commercial, and open source software, all trying to solve various technological problems in support of the real work being done by the organization.”

Sandra Ordonez, a self-described “Web astronaut” and external communication lead for Joomla, the open source CMS, became Wikipedia’s first communications director in 2005. She says geeks like Wikipedians often turn into zealots out of necessity.

“When you have a project like Wikipedia that’s trying to be a good encyclopedia, you need to enforce certain rules to make sure it stays that way,” she says. “The site is harassed on an hourly basis by people who are trying to use it for self-promotion, which makes them much bigger sticklers about enforcing the rules. Wikipedians get a bad rap for being obsessive-compulsive, but that’s exactly what you need to be successful.”

How to escape: Heresy depends on zealotry and belief in the power of “evangelism,” says O’Berry. You can avoid it by keeping your mind open and your eyes on the big picture. “The minute you begin to treat something like a zealot, you reinforce the notion that it’s a religion,” he says. “It’s not religion; it’s business. The world survives on compromise. Go too far in one direction or the other and you’ll never solve any problems.”

7th circle of IT hell: Vendor-on-vendor violence
Description: A dismal miasma full of ogres with $200 haircuts, wielding Louis Vuitton briefcases
People you meet there: Lawyers

In the IT world, violence against individuals is regrettable but fortunately rare. But violence between companies is not — and the collateral damage is often far more extensive.

“When companies can’t compete fairly, they get predatory,” notes O’Berry. “That’s when all the patent lawsuits start popping up. SCO was probably the worst example, but it’s hardly the only one. It’s a violent way to do business.”

Spreading fear, uncertainty, and doubt about your competitors; using a monopoly in operating systems to gain advantage in applications and other software; partnering with companies with the intent of gutting them later; the tech world is rife with vendor violence.

The real victims? Consumer choice and industry innovation.

How to escape: Exiting the circle of company-on-company violence may only be possible via collective action, says O’Berry. “When you squeeze the ecosystem only to your advantage, not caring about the companies you’ve killed along the way, eventually people will say enough is enough,” says O’Berry. “We need to balance our capitalistic nature with some form of societal responsibility.”

8th circle of IT hell: Fraudulent practices and malevolent hackers
Description: A slippery pit of deception where daemons lurk in the shadows and nothing is as it seems
People you meet there: Scammers, spammers, black-hat hackers, and rogue system administrators

The eighth circle of IT Hell is populated by black-hearted souls who’ve abused their access privileges to steal money, data, and intellectual property, or simply do damage in response to some perceived wrong, says Adam Bosnian, executive vice president at Cyber-Ark Software, a maker of privileged access management products.

For example, the Société Générale scandal in February 2008 stemmed from one person having too much access to too many sensitive systems, says Bosnian. When bad actors are allowed to aggregate access privileges, it puts them in an excellent position to commit fraud.

“When you mix human frailty, malevolent actors, and power, bad things can happen,” he says.

How to escape: You can avoid falling into the circle of fraud by doing a better job of monitoring access privileges, says Bosnian. “The people with the most power — systems and network admins — are often not controlled in any way,” he says. “You need to be able to see what they’re doing and control it at a granular level. When people know they are being monitored, they tend to keep their noses clean.”

9th circle of IT hell: Tech-pro treachery
Description: An icy wasteland, filled with lost souls desperately clawing at the knives in their backs
People you meet there: Disgruntled employees, work rivals, any geek with a grudge

Jealousy, backbiting, subterfuge, and sabotage — they’re all just unfortunate, if rare, parts of the IT life, says Anthony R. Howard.

Howard says he once took a senior technology architect job with a major hardware maker that was coveted by “Bob,” a less experienced employee in another location. Bob then attempted to cut him off at the knees by obtaining the RFP for a supercomputer for a major client and keeping it a secret — even from the head sales rep.

“He thought he could do it himself and thus prove he should have gotten the job instead of me,” says Howard. “But Bob was in way over his head. So he began blaming me for why the project didn’t get done, when I didn’t even know about it.”

One week before the design was due to be submitted, Howard learned what had happened. Fortunately, Howard says, his own boss saw through the scheme immediately. Bob was asked to produce all of his email communications about the project. When he couldn’t, the jig was up.

Howard says he had to spend all of his Labor Day weekend working on the project and fixing Bob’s errors.

“I was able to bring in the design on time,” he says. “But Bob had to leave.”

How to escape: It helps to have a good manager on your side, says Howard. But you still need to cover your assets, keeping all your emails and your boss in the loop. If it looks like treachery is afoot, pick up the phone or go to your nemesis’s office to professionally confront them — don’t do it on email.

“Small people with large egos act like giants on email because they don’t have to face anyone,” he says. “If you talk to them on the phone or meet with them, they have to be their real size.”

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