Life is filled with competition, from the highly stylized and advertised (beauty pageants, the Olympics) to the small and largely unnoticed (the runner down your street working to beat her personal best or the local kids' soccer tournament). In the IT industry, we usually measure competitive success in terms of money or market penetration. For example, you might remember the hoopla when Microsoft Exchange Server became a billion-dollar product, or consider the continuing arguments over whether iOS or Android is the best mobile OS based on metrics such as number of units shipped or unit revenue.

I want to propose a different type of competition: What's the worst software in the world? More specifically, what's the worst software in the Exchange Server world? To illustrate some guidelines, let me tell you a story about a real contender.

My girlfriend is smart and technically literate, but not an IT person. The other day, I got a series of instant messages from her asking me questions about file recovery in Intuit's TurboTax. She was working on her taxes using the standalone TurboTax program, which crashed. When it crashed, she lost all her work-several hours' worth. How is this possible? In their infinite wisdom, the folks at Intuit have decided that TurboTax, unlike practically every other productivity application in the entire world, shouldn't automatically save its work.

To be fair, there's an article in the TurboTax knowledge base that mentions this, but . . . seriously? It's 2012, and your application doesn't prompt users to save their data or do it invisibly in the background? Congratulations; you've been nominated for the Worst Software in the World list. After this experience, I'll go out of my way to recommend not using TurboTax, now or ever. (Honorable mention goes to Intuit's Quicken for Windows, which is bug-ridden, unstable, and unnecessarily difficult to use, which is why I don't use or recommend it any longer, either).

Her story outlines the judging criteria for the Worst Software in the Exchange World contest. (OK, maybe it's not a contest because I can't imagine anyone would want to win.) To "win," an application should score well in some or all of the following categories:

  • It should present a significant risk of data loss when used normally, either due to flaws in its design or major bugs.
  • It should have a measurable and detrimental effect on performance or stability.
  • It should have an ugly, uncomfortable, or unpleasant UI.
  • It should work only intermittently for its designed purpose.
  • Its documentation or support should make it difficult to work around any of the preceding problems listed.

I'm accepting nominations via email between now and April 15. In the April 19 UPDATE column, I'll present the nominees and put the winner to a vote. You can nominate older versions of software (e.g., you can say, "Version 3.4 of product X is the Worst Software in the Exchange World because . . ." even if the current edition is an updated version) but nominations of current product versions will receive preference.

What will the winner receive? I guess that should be a separate category of suggestions or nominations, but please keep them a) clean, and b) legal.