InformationWeek's Most Important Cover Stories

Jun 24, 2013 (04:06 AM EDT)

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Our June 24 issue of InformationWeek is our last print issue, as media industry forces move us in a wholly digital and online direction. To celebrate InformationWeek's rich 28 years as a print magazine (its predecessor was a tabloid newspaper called Information Systems News), the editors selected 25 of the best covers and cover stories from more than 1,300 issues.

This slideshow isn't the definitive list -- you as readers and IT professionals are the ultimate judges of what's important and worth reading, and we'd love to hear your opinions on the biggest and best business technology stories of the past three decades in the Discussions section below.

Among the magazine highlights we selected: Our inside story on the beginnings of Microsoft's battle with the U.S. Department of Justice (August 1994); our burial of OS/2 Warp (August 1995); our early look at the Y2K time bomb (February 1996); our exclusive interview with IBM chief Lou Gerstner (February 1998); our prediction of's coming cloud clout (November 2000); our castigation of Microsoft's buggy software (February 2003); our iconic "lipstick on a pig" report on the state of ERP (July 2006); our touching tribute to missing data scientist Jim Gray and the industry's massive search for him (April 2007); our critical analysis of the security industry's "epic fail" (October 2010); and our exclusive analysis of General Motors' about-face on IT outsourcing (July 2012).

Throughout my two tours and 10 years at InformationWeek -- 1996 to 1999 and 2005 to present -- we've always prided ourselves on our close connection with our readers: the talented business technology executives and other professionals at the center of the world's greatest industry and global economic growth. Our credo has been to delve into the innovative technologies, companies, organizations and people making a difference.

We assure you that our commitment to that principle, to our audience members/readers, and to the very highest standards of reporting, writing and analysis will carry on in the 50-plus PDF-based magazines we will continue to deliver each year, as well as in the 25 to 30 articles and other content we create daily on As always, you can tell us what we're doing well and not so well by dropping me a note at

Meantime, we hope you enjoy this stroll down memory lane. We sure did.

Download PDF of "The Future Of MIS"

"MIS managers," we called IT leaders back then. Our cover story on Dec. 1, 1986, not long after the birth of InformationWeek as a glossy magazine (its predecessor was a tabloid newspaper called Information Systems News), attempted to divine what the profession would look like in 13 years. We got a lot of things right: It will be less about processing data, ensuring uptime and operating/managing centralized hardware, we predicted, and more about integrating systems, supporting business processes and delivering business value. Said one wag: "MIS will be getting more heavily involved in the strategy of the business they support, more concerned with environmental issues, competitive pressures, regulatory problems and cost considerations." Not bad for 1986. We weren't so prescient about the title destined to replace MIS chief: Information Resource Director, anyone?

Download PDF of "Justice V. Microsoft: The Inside Story"

During the one year that InformationWeek was sold on newsstands nationwide, before converting back to a pure "controlled circulation" model, we had to grab a wider swath of readers than just the most-involved business tech pros. What better subject than an inside look at Microsoft's antitrust negotiations with the U.S. Justice Department? DOJ attorneys painted Bill Gates as the chief negotiator from behind the scenes, an approach that frustrated the department until, in the final hours, lawyers from Microsoft, DOJ and the European Commission gathered with Gates on speakerphone to hash out a deal. Microsoft agreed to end the most-restrictive parts of its operating system licenses with PC makers. Rivals IBM and Novell cheered the deal; an IBM exec said "a window of opportunity has opened." That window wouldn't stay open for long.

R.I.P. Warp?

We didn't quite have the cojones (metaphorically speaking) to remove the question mark from our cover headline, which we added to hedge our prediction that IBM's OS/2 Warp desktop operating system was finished in a Windows world. IBM still cried foul when it read the story, in which we suggested that even in the enterprise OS market, IBM would eventually lose to Microsoft, its former OS/2 partner. Big Blue would quietly pull the plug on OS/2 in the coming years, supporting customers mostly in banking before ending all support in 2006. Its withdrawal was another testament to the fact that even strong technology doesn't always win.

Split Decision

We were a few hours away from closing the weekly magazine and shipping the pages to the printer when AT&T CEO Robert Allen announced that the company was splitting itself up, more than a decade after the government forced the breakup of the original Ma Bell into seven independent Baby Bell local telephone companies, leaving AT&T as a long-distance company and network equipment maker. We had to scramble. Our designers created a new cover featuring the AT&T logo broken into three pieces, representing the three new companies: AT&T for long-distance, Lucent for network infrastructure and NCR for computers (since the Ma Bell divestiture in 1984, AT&T had acquired NCR and moved into that business). Reporter Mary Thyfault raced to get details and reaction, crafting a story that analyzed the business and customer impact. It wouldn't be the last AT&T breakup: In October 2000, the company split into AT&T Wireless, AT&T Broadband (cable TV) and AT&T (still long-distance). But, thank goodness, not on deadline.

The Y2K Problem: Time's Running Out

It was "the biggest single information systems project the world has ever seen," said one CIO. It was early 1996, and Y2K update and replacement work was starting to consume IT departments worldwide. It would cost companies an estimated $400 billion to $600 billion to ensure that their systems didn't fail because of a programming date-field shortcut. Banks were particularly vulnerable because so many of their functions are based on the time-money equation. Our cover story, "Time's Up," was a warning: If you're not already on the Y2K case, get on it -- and make sure your supply chain partners do the same. People still debate whether the mad Y2K scramble was much ado about little, since the year 2000 arrived with barely a computer glitch. Perhaps Y2K was the most expensive better-safe-than-sorry project the world had ever seen.

We Are The Business

Even to this day, pundits pine for IT-business "alignment," as if technology is some separate entity to be joined with business functions as part of a therapy intervention. InformationWeek has always taken a different view: IT is fundamentally inseparable from "the business," and in fact is the business, with the same end goal of boosting profits, delighting customers and maximizing shareholder value. Featured on our Oct. 28, 1996, cover was GE CIO Gary Reiner, one of the five execs at the company who reported to chairman and CEO Jack Welch -- no slouch when it came to demanding results. Backing up our thesis was a study by MIT prof Erik Brynjolfsson, which found that customer-oriented strategies of our InformationWeek 500 companies at the time were "associated with the profitable use of IT. ... Other companies stressed control and reporting from IT, and they were not as profitable."

IBM Means E-Business

In 1998 there was no bigger interview in tech than Lou Gerstner. Even before Gerstner was officially named IBM CEO, the race to score the first sit-down interview with him was underway. And throughout Gerstner's first year, InformationWeek's Brian Gillooly and the late Bruce Caldwell campaigned Gerstner's handlers to convince them that InformationWeek was the right venue when he was ready to talk with the press. They succeeded. On the day of the big interview, Brian recalls having to head to a restroom at IBM headquarters to compose himself. The resulting article focused on IBM's new push into "E-business" and the billions of dollars and tens of thousands of employees it was shifting to deliver on that hardware, software and services strategy. The editors of InformationWeek's three main competitors, meanwhile, wrote a joint letter to IBM protesting its "unfair" decision to grant us the exclusive. They apparently didn't understand that such interviews are earned, not bestowed.


Remember the era of e-everything? E-commerce spawned e-retailing (or the dreadful e-tailing), e-trading (E-Trade once sent us a cease-and-desist order for using its trademark), e-vangelism and a rash of e-spinoffs. Add to that rogues' gallery the overarching theme of "e-transformation," which we put forth in a cover story that, in hindsight, was a paean to the irrational exuberance of the time. It was the Enron era. Emerging "e-marketplaces" promised to change the face of industries -- Enron in energy and telecom, Covisint in autos, Elemica in chemicals and RosettaNet in electronic components -- vowing to connect buyers with sellers in real-time bliss. E-marketplaces fizzled, and most of the companies went bust or morphed into more conventional supply-chain management vendors or standards bodies.

Software Morphs Into A Service!

We got the big trend right: Enterprises would increasingly deliver software as an online service. The moniker back then was "application service provider" rather than cloud or SaaS provider. But we hear about the same benefits almost 15 years later: Customers can implement software-as-a-service more quickly than on-premises versions and focus more on producing business results and less on managing software. What's surprising in retrospect is two of the main vendors that were touting this movement: Oracle and Microsoft. "All the major software companies are going to have to become ASPs," said Oracle CEO Larry Ellison. Microsoft's Steve Ballmer envisioned desktop and collaboration software becoming a service "over time." formed that year, but it would be another five years before it bagged a 1,000-subscriber customer. Spotting long-term trends is one thing; knowing when they'll take off is another.

The 12th Annual InformationWeek 500

Our 12th annual InformationWeek 500 was our biggest print magazine issue ever, a veritable phone book at 532 pages plus covers. The dot-com bubble was starting to bulge at the seams. It seemed as if technology advertisers, large and small, were printing money, and our sales team wasn't averse to collecting some of it. A look at our masthead in that Sept. 11, 2000, issue reveals more than 60 full-time InformationWeek editors, reporters, researchers, photographers, designers and other editorial staffers. We actually employed a full-time editor year-round just to help us produce that one InformationWeek 500 issue. (But no staff sous chef or massage therapist. The largesse went only so far.) The No. 1 company in that year's InformationWeek 500 ranking? 3Com, now part of Hewlett-Packard, followed by CIT Group, Compaq Computer, Avnet, Cisco, Reliant Energy, Sprint, Boise Cascade, Bristol-Myers Squibb and Arrow Electronics. As for the cover illustration, is that a crane suspended in midair latched onto the elevated 5 in 500? Perhaps even cranes defied gravity and other laws of physics in those lofty times.


InformationWeek strives for cover art that's attention-grabbing and edgy. But cute? There's no other way to describe the cover photo for our Sept. 25, 2000, article on IT pro burnout, featuring then-Credit Suisse IT manager Michael Miller with his son, Mikey, in a matching white shirt and tie. Our cover, "Balance Or Burnout," struck a chord with readers feeling the stress of runaway success. Jobs and bonuses were abundant in September 2000, but the Web had every company dreaming about tech-fueled riches, from dot-coms chasing IPOs to established companies spinning out Web operations. The romantic notion of trading long hours for a stock-option windfall was starting to collide with the reality of failed companies and strained relationships. Job hopping was rampant: A 25-year-old consultant described going to a "portal-software startup" for six months before bouncing back to his old gig. The tech bubble caused some of the burnout, but some of the pressure was here to stay. IT pros lamented how the Web demanded faster development cycles and constant iterations. And since most Web work was customer-facing, "people are given a task and then all of a sudden they have to wait for the marketing people," an IT manager bemoaned. Thirteen years later, and IT's still trying to get its relationship with marketing right.

Amazon's IT Agenda

Jeff Bezos never looked so buff. By November 2000, it was becoming clear that the IT infrastructure of fast-growing was, in our words, "in serious need of bulking up." To drive that point home, we superimposed Bezos's smiling face on the body of Charles Atlas and put a cartoon image of the Amazon CEO on the cover of our magazine. At the time, Amazon had doubled tech spending over nine months, from $102 million to $200 million. The money was going toward a new data warehouse, logistics and marketing software, Web infrastructure and a second data center. The upgrades were needed to support the company's booming Web-based retail operations, but they also became the foundation of a new business, Amazon Web Services. Amazon had just begun "decoupling" system components to let other e-commerce companies integrate AWS's site features into their own sites. By 2003, Amazon would draft a business plan for sharing more of its functionality as services through APIs. The next year, it introduced its first public cloud offering, Simple Queue Service. Today, Amazon still doesn't break out the revenue it generates from cloud and other IT-based services, but analysts put it above $2 billion annually.

Standing Strong

InformationWeek was holding its annual IT leadership conference on Sept. 11, 2001, when the World Trade Center and Pentagon were attacked by terrorists. Scrapping our agenda, we gathered our 300 attendees to discuss the day's events and just come together. We asked Owens & Minor CEO Gil Minor to get the conversation started, and he began: "I'm going to need some help on this one." His humble reaction captured the incomprehension and sense of loss everyone felt. Elsewhere across the country, IT leaders were springing into action. Those at insurance company Marsh, the Port Authority of New York and New Jersey, and law firm Sidley Austin helped their companies cope with lost colleagues and the destruction of major offices and IT infrastructure. The New York Board of Trade's trading pits were gone. The American Stock Exchange was the first company permitted to return to offices around ground zero. FedEx and Continental Airlines dealt with grounded planes. For their work, our Dec. 3, 2001, issue recognized the CIOs of those seven organizations as our Chiefs of the Year, a recognition that for 14 years we had given to one individual. The eighth person recognized in that issue was Wendy Faulkner. A VP of IT at Aon Risk Services, Faulkner had a soft-spoken way of leading people to work together, like offering a "we're not practicing our team-building skills" reminder to defuse tense moments with humor. Faulkner, a 47-year-old wife and mother of two girls, was killed in the World Trade Center attacks while attending a meeting at Aon's offices.

Troubling Discovery

We tackled the ugly problem of child pornography on workplace computers in the spring of 2003, shortly after two PC technicians at New York Law School who had discovered thumbnail images of naked children on a professor's laptop were fired after turning him in. What happened? One of the technicians, Dorothea Perry, may have angered her employer, Collegis, a service provider to NYLS, or the school by going to the FBI when she wasn't satisfied with the pace of the investigation. Despite good employment records, Perry and colleague Robert Gross were put on probation for minor workplace offenses such as tardiness, then fired. Perry and Gross sued Collegis and NYLS, alleging retaliation against them. Gross settled, but Perry entered a protracted legal battle that didn't go in her favor. Even so, their actions led to the arrest of law professor Edward Samuels, a guilty plea and jail time. The episode served as a warning to IT pros: If you encounter child porn, take action, but proceed with extreme caution.

The Programmer's Future

2003 was a year of soul-searching for IT pros. The tech bust had slashed the number of IT jobs from 2000's peak. Offshore outsourcing shot to prominence, and companies were ditching custom coding for off-the-shelf software. Just 18% of IT pros considered the career as promising as it had been five years before. Our Nov. 17 cover story on "The Future Of The American Programmer" encapsulated the angst through the lens of the profession most at risk. "The lower echelons of skill levels are going to be washed away," warned Archipelago CTO Steve Rubinow (later NYSE Euronext's CIO). Since then, the U.S. IT profession has survived outsourcing, and another recession, and is among the healthiest job segments. But Rubinow's prediction came true. About 432,000 people are now employed as programmers in the U.S., down from 700,000 in 2000. The dip's partly due to changing Labor Department definitions, but much of it is from a changing workplace that forced people to reinvent themselves or leave the profession.

You Call This Trustworthy Computing?

Readers at the time were so fed up with the nonstop security flaws in Microsoft's software that we decided to hit the company where it hurts: on its iconic Windows logo. Our Feb. 14, 2005, magazine cover featured the logo covered with roaches, centipedes, beetles and other arthropods, under the headline "Bugged Out!" It was a pivotal time for Microsoft. Our cover story by John Foley reported that a week earlier, Microsoft had released a dozen software patches, many of them deemed critical, to fix 17 vulnerabilities found in Windows, Internet Explorer, SharePoint and Office -- essentially, the crux of the company's software portfolio. Chairman Bill Gates was due to speak within days at the RSA Conference in San Francisco. While customers gave Microsoft credit for making progress on security, most criticized its three-year-old "trustworthy computing" strategy as a frustrating work in progress. Fortunately, Microsoft was able to turn things around. At RSA it introduced security patches and service packs for a broader range of products, in the form of Microsoft Update. Its rally around software development best practices resulted in more-secure code overall, and Microsoft expanded its security capabilities through acquisitions.

ERP Gets A Complete Makeover

We've always prided ourselves on the quality of our cover art and other graphical images. Our July 24, 2006, "lipstick on a pig" cover, a not-so-subtle poke at vendors' superficial efforts to remake their ERP software suites, was a particularly big hit with readers. The related story by senior editor Rick Whiting -- "You Look Marvelous: But is there more to next-generation ERP than lip gloss and eye shadow?" -- detailed product enhancements from SAP, Oracle and Microsoft. We received lots of requests for the cover artwork, by illustrator Mick Coulas (Google Mick's name for a sampling of his other work), which readers said they wanted to hang on their office walls. Wrote one reader: "Our vice president of sales has kept your July 24, 2006, issue on his desk since he received it. After reading it cover to cover, he left it for all to see because -- well -- he just loves the cover art." In a 2008 online poll in which we presented reproductions of 50 of InformationWeek's best magazine covers over two decades, readers voted the porcine princess their all-time favorite. Marvelous indeed.

What's The Greatest Software Ever Written?

InformationWeek's "The Greatest Software Ever Written" drew on writer Charles Babcock's decades of experience covering software development. Because Charlie judged software breakthroughs "in their historical context," everyone could debate the list and supply alternative candidates. It quickly became our most-read online article to date, and in the days that followed about 300 readers shared their opinions, in an unexpected outpouring of memories. (That rich discussion, alas, was lost in a content management system changeover a couple of years ago.) The Apple Lisa, not the Mac operating system (No. 8), should have been on our list, wrote Michael Bell at Medco. Why not John Kemeny's Basic instead of Java (No. 5)? asked Oscar Shultz at CSC. The Morris worm (No. 12) shouldn't have been on the list at all, said another reader. Babcock laid out clear criteria. He wasn't interested in science projects; the code not only had to be technically brilliant, but it also had to be widespread in the real world. Excel made our list (No. 9), but not Windows or Word. And No. 1? That was BSD Unix, for its impact on the Internet and Linux, and for the philosophy behind it that software "should be a freely available extension of man's intellectual powers -- a force that changes his place in the universe." Software expert Ed Yourdon, author of the Yourdon Report, called our list "a darn good starting point, if not the last word."

Why The iPhone Won't Make Apple A Player In Business IT

We were wowed by the iPhone from the start. We put it on our cover after its unveiling and wrote that Steve Jobs "made a wake-up call from a phone that doesn't exist," since you couldn't buy one for six months. We knew from people's euphoric reaction that it would force IT to get more serious about mobile computing. But we grossly underestimated how Apple would ride the bring-your-own-device movement and make iPhones a mainstream business tool. We quoted one IT leader who said that giving employees an iPhone was like giving them a PlayStation. We acknowledged some top execs would bring them to work and demand to use them, but we didn't see BYOD going way beyond that to include swaths of employees. The "app for that" ecosystem? We didn't see that coming, either. So we left readers with this gem: "There's reason to suspect the iPhone's business impact could be similar to the Mac computer's: much admired, indispensable for visually intensive niches, but not the mass-market tool on which companies run."

The Search For Microsoft Researcher Jim Gray

On Jan. 26, 2007, Microsoft distinguished engineer Jim Gray sailed out of San Francisco Bay on a lone voyage to the Farallon Islands. Neither he nor his boat, Tenacious, were ever seen again. Gray's disappearance sent shock waves through the tech industry, setting off a frantic, 16-day search that included the use of large-database technologies that Gray helped pioneer. Colleagues and other volunteers pitched in using satellite imagery, data modeling and Amazon's Mechanical Turk engine to search for clues. In the end, his fate remains a mystery. Gray's wife, Donna, commissioned a sonar search of the seabed for the wreckage of her husband's boat, a search that turned up a few matching 40-foot wrecks, but none of them her husband's.

The loss hit home with InformationWeek's editors because some of us knew Gray personally. Editor-at-large Charles Babcock crossed paths with Gray several times in his coverage of database technologies, and as an avid sailor in his own right, Charlie brought that expertise to bear in the poignant cover story he wrote. (Donna Gray thanked Charlie for his personal touch in reflecting on her husband's legacy.) InformationWeek's John Foley may have been the last journalist to interview Gray, a winner of the prestigious Turing Award, before he vanished. Gray's words in an email exchange with John were prophetic: "There are just not enough gurus to do all the things that can be done."

Three Scenarios For How Microsoft's Open Source Threat Could End

Microsoft's Steve Ballmer was quoted in 2001 as saying that "Linux is a cancer that attaches itself in an intellectual property sense to everything it touches." Years later Bill Gates would equate the open source movement to communism. In our cover story of May 21, 2007, editor-at-large Charles Babcock reported that Microsoft was still at it, asserting that 235 of its patents (it wouldn't quite say which ones) were being infringed by the Linux operating system, OpenOffice application suite and other open source code -- and implying that it was ready to haul customers of that offending software into court. Our magazine cover "Play By Our Rules Or The Penguin Gets It," featuring a gun held to the Linux penguin's head, poked fun at Microsoft's tough guy stance. It was our homage to National Lampoon's famous "If You Don't Buy This Magazine, We'll Kill This Dog" cover of January 1973. Wrote one reader: "Kudos and huzzahs on the May 21st cover. I haven't seen a more enjoyable cover since National Lampoon. Thanks for the chuckle."

Outgunned: How Security Tech Is Failing Us

It was IT's dirty secret: Spending millions of dollars on security products such as firewalls, antivirus and intrusion detection bought companies little more than ticks in an auditor's checkboxes. Greg Shipley, a respected security consultancy CTO, laid that secret bare in a parting manifesto before joining In-Q-Tel to help the U.S. government spot innovative tech startups. The result: our cover story titled "Epic Fail." Some vendors cried foul, but Greg backed up his thesis with extensive testing of five major antivirus suites that showed detection rates of no better than 30%. His message that you can't buy security came with an action plan. Spend on controls in line with threats. Get realistic about detection. Reward innovative vendors. Know when tech isn't the answer. Since then, the strategy of focusing on risk, process and awareness training has caught on.

IT Is Too Darn Slow

IT is too darn slow. This idea came to us as we talked with CIOs. Manpower trying cloud development. FedEx reinventing its data centers. The FBI using agile development. IT leaders saw their teams slowing down their companies and agencies. Why? Cloud computing and consumerization had raised expectations, but the biggest reason was that IT had become an indispensable customer-facing resource. Readers responded. Companies got what they paid for, some said, pointing to underfunded or outsourced IT shops. Some worried that IT was just chasing new fads. Others rallied behind our call to action. One IT manager said he sent our story to his vacationing boss to read on the beach. One CIO agreed with our call but said his C-level peers were a bit too happy to show him the article. Another CIO put this cover on her office wall, a reminder to all who entered.

Hana and Exalytics: SAP's Hype Versus Oracle's FUD

SAP had been talking up its Hana in-memory database for years, promising "breakthrough performance," "dramatic simplification" and "never-before-possible applications." Hana intends to replace conventional databases, so no surprise that Oracle, the No. 1 seller of databases, was sowing seeds of fear, uncertainty and doubt about the new technology. Who was right? Our article parsed fact from fiction, reality from twisted interpretation. SAP and Oracle had their nits with Doug Henschen's article, but both conceded it was fair. Their battle is still raging, with SAP recently claiming that Hana is ready to run core transactional applications such as ERP. Our "Hype Vs. FUD" piece is still widely cited as the most detailed technical and market comparison of two very different deployment options for tens of thousands of customers.

General Motors Will Slash Outsourcing In IT Overhaul

It's what happens when you combine years of experience covering an industry with years of experience building relationships with the industry's heaviest hitters: Our exclusive story on General Motors' plans, in the wake of a government bailout of the company, to hire thousands of IT employees in the U.S. and reverse its historical reliance on outsourcing. News organizations nationwide jumped on the story we broke. We called it like we saw it: CIO Randy Mott was guiding a high-risk plan that crams a daunting amount of change into a three-year window, at a time when the company was still in a precarious recovery from bankruptcy. That CEO Dan Akerson would take on that level of risk showed just how essential having the right data and technology is to GM's future.