Microsoft’s had a variety of weird and wonderful consumer devices over the years that haven’t gone so well. Jon Friedman, now chief designer of Office 365, has been at the center of Microsoft’s notorious product failures, including the SPOT watches from 2004, ultra mobile PCs, the KIN phone, and the unreleased Courier device. At Microsoft’s Build developer conference this week, Friedman reflected on his personal career at the software giant and why some of these products weren’t successful.

“We were ahead of our time, Bluetooth phones weren’t really around, the smartphone hadn’t really taken off,” explains Friedman, discussing the Smart Personal Objects Technology (SPOT) watches. Microsoft released these SPOT smartwatches in 2004, powered by a FM radio sub-carrier technology to deliver news and information to a wearer’s wrist. “We had a good experience, we learned a lot,” says Friedman. “We gave up a little too early I would say, it was a side project and Bill Gates loved it.” Gates even referred to it as “a computer on every wristop,” but ultimately the project ended four years later in 2008.

Friedman then moved on to something new at Microsoft, the idea of small tablet-like PCs. These PCs were available 12 years ago, before the iPhone and iPad. “We had this great idea, it was the 7- to 10-inch slate device, super thin, instant on, always connected, capacitive touchscreen for $400,” explains Friedman. His team needed 300 people in two years to go build these devices, but instead it got 20 people for six months because Windows Vista was launching and Microsoft wanted to cram the touch unfriendly operating system onto these devices. “So of course it becomes this resistive touchscreen, super-fat PC, two hours of battery life, and $1,200,” reveals Friedman. “I designed some really crappy software that run on top of it so you could actually touch Windows Vista, so that was that.”

After the ultra mobile PC flop, Friedman joined a new incubation team inside the Xbox team. “We were working on a social mobile phone, KIN, it was on the market for a whopping six weeks,” jokes Friedman. “My mom bought one, I feel really bad about that. I think we sold about 8,000 of them.” Microsoft launched the KIN phone with Verizon, but it didn’t last long because the company was in the middle of pivoting its Windows Phone strategy to focus on a single operating system. “It actually was quite cool, this was the beginning of cloud computing,” explains Friedman. “There’s a lot of wonderful things about it, but Windows Phone was kind of pivoting and KIN and Windows Phone didn’t have a clear strategy. At some point in time it made sense to move forward with one platform.”

Microsoft’s next incubation project involved a dual-screen digital journal, codenamed Courier. “Courier was really about bridging the divide between the analog world and the digital world,” explains Friedman. Concept videos and images leaked of the dual-screen device, and it captured the imagination of the internet and became popular without ever being a real and functional product. “We’re still working towards pen and ink, we’re still building this idea of bridging the divide,” says Friedman. “The reason Courier got killed was that it was another side project, it was another thing we were playing with and it didn’t have a clear developer story or clear platform story.”

Steve Ballmer killed courier and he visited the offices of the team responsible to explain why, but ultimately the device had a good user story but not a fully supported platform behind it. Friedman explains that the cancelation did decimate a culture inside his design teams, and that the company “lost a lot of great talent at the time.” Friedman claims both Courier and KIN were canceled at the same time, in the same week. “It was a bit of a devastating moment in my career.”

Friedman is still at Microsoft and he’s now responsible for the design of Office 365. Friedman held a similar talk at a design conference in Seattle two years ago, but this is the first time he’s spoken at Microsoft’s own conference about past product failures. The timing of Friedman’s talk is ironic as Microsoft is now rumored to be working on a Courier-like device for taking digital notes. The mysterious device has been spotted many times in patents from the Surface team, and reports suggest it will include dual displays with a unique hinge and a special notepad app to mimic writing like a real notebook.

It’s not clear if Microsoft’s mysterious Surface device, codenamed Andromeda, will ever make it to market, but Friedman’s talk does show that the company is aware of its past failures and is trying to learn from them.