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Playfulness & Serendipity in Product Design

Some ideas for how we can design deeply meaningful experiences that leverage intimate customer data and insights without being creepy.

I spent three years at Microsoft with R&D teams working on a reoccurring theme: how do we leverage machine intelligence and vast customer understanding to create highly personalized and meaningful experiences — without being creepy?

While working on a conversational agent project looking to anticipate users’ queries and behaviors, we noticed that even a high degree of accuracy (90%+) wasn’t enough to offset the loss of trust from failed insights. In addition, the variable level of tolerance for data privacy and uncanny insights made this problem especially challenging.

It occurred to me that the problem wasn’t about accuracy or disclosure, but the expectation that technology is based on a practical exchange of information — it has to be either right or wrong. What would happen if it was OK for the insights to be wrong? What if the exchange was more playful and could lead to the user changing their minds about their perceived outcome?

These ideas led to a number of experiments dealing with new interaction form factors (physical, temporal, conversational) and serendipitous outcomes.

One project in particular I’d like to focus on is called The Serendipity Watch, which leads to unexpected connections with friends or a surprise family vacation.

Ammon Haggerty

Hi! I’m a 25+ year veteran of the IxD industry, with the majority of my career being focused on creative engineering (visual/UX design + front-end engineering). I’m VP of Design at Formation (, a software company that I co-founded. Prior to Formation I was a Principle UX Designer at Microsoft, worked in the creative agency world for 10 years, and worked with many startups.

I’ve also been a professional club DJ and have found boundless inspiration from music in my work. A longtime obsession of mine is building a detailed music classification system and discovery methodology.

The last major talk I gave was in 1999 at the Adobe Max conference (then Macromedia Max) to more than 1000 people. Since then my speaking engagements have been smaller and not as public (internal talks at Microsoft and BCG/DV).

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