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This is a guest post by Brad Anderson, Corporate Vice President, Enterprise Client & Mobility.

Every year I meet with hundreds of IT Pros and IT leaders to talk about the day-to-day needs and requirements of the industry. I come away from these discussions excited to take their feedback and apply it to the products and services we’re building – and sometimes I leave those meetings with a couple new tales of IT woe.

You know the types of stories I’m talking about – big mistakes from end users or system malfunctions that are, perhaps unintentionally, pretty funny.

With this in mind, we’re launching a new storytelling contest called “Tales from Tech Support.”

We want to hear your stories – the ones that are so unbelievable, so terrible, and (in retrospect) so hilarious that they just have to be shared.

The contest begins today, and you can submit your stories here.

Share your story between now and February 15, and then, once all the submissions are in, I’ll sit down with a team here at Microsoft to select the top finalists. Once the finalists are chosen, we’ll open it up to an online vote to determine who wins the grand prize.

Also, during every week of this contest there will be a random drawing to give away a Microsoft Band and $50 Starbucks card to someone who submitted an entry.

The grand prize at the end of the contest will be a Surface Pro 3 + keyboard.

Just keep a couple things to keep in mind when writing your stories:

  • Personal names should be first name only, and don’t call out the name of the company or your employer (hopefully this is obvious)
  • All stories must be true and appropriate (again, hopefully this is obvious)
  • It will take up to 24 business hours for new entries to appear in the gallery
  • This is for United States residents only
  • Full contest rules are here
  • And don’t forget the privacy policy

We want to have some fun with this, but there is another goal as well:  All too often these kinds of stories are rooted in poor or complex design of the products and services being used, and we want to fix these kinds of experiences. Consider this personal example:  When I started in this industry, I worked on the front lines of Customer Support. One night, while working a graveyard shift (midnight to 6:00am), a customer called in tears. He was replacing a failed disk system and, when he went to re-mirror a set of disks for fault tolerance, he configured the mirroring in the wrong direction. He had no backup and had just mirrored an empty disk over his disk with data. The user experience never should have allowed that. On a lighter note, I had a customer call and ask about the cup holder that kept extending from his PC J.

The IT profession will always be a great source of stories about human error and the gap between technological sophistication and technology usage.

I can’t wait to read your stories and follow them on Twitter via #TechTales. Good luck!