Dec 12, 2022Liked by Steven Sinofsky

Personal (but related) story: in 2018 I released a new version of my app that had been developed over 20 years at this point for different platforms and had many customers using it who had been with me over that entire lifetime. At this point I had ~400k monthly actives on a few different variants of the app. The new version, 5 for iOS, was the culmination of a lot of years of thought about the product and was, to me, the definitive version.

My customers hated it, they were upset about it, and let me know in no uncertain terms that I had screwed up. So I mea culpa’ed and immediately switched to version 6, which I launched in late 2018. It was different from version 4 but not as drastic. An evolutionary change instead. I still had customers say it was a massive departure and complain, and then I’d patiently answer all their questions and their rants and ask them to try it and they liked it better. Didn’t matter though as I shed lots of users either because they didn’t move to the new product or left my products altogether. The net effect is that for the first time in my professional career I had to find a job working for someone else. (Four startups in 20 years. Lots of happy users, no exits for me. It’s harder than the survival bias will make you believe.)

I spent a lot of time thinking about that and thinking about how Apple can get away with it and Microsoft can’t. Apple always forces users forward, and they are constantly evolving, but that evolution, for the most part, comes in tiny little drips. We almost don’t see it happening until suddenly we look back and realized how different it is. (Not all the time but they are really good at step change.) Microsoft, in my mind, has a different problem: MS is so conscientious about backward compatibility that any departure feels massive. Customers just don’t expect it and are unhappy when a large change occurs, even if it isn’t really a large change. (Our greatest strengths are our greatest weaknesses.)

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Thank you for sharing your story. I really appreciate the experience you went through. I tend to agree with your observations about the differences between Apple and Microsoft.

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