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The semi short answer is that we've been developing our mobile apps which has seen the bulk of mobile adoption, and the old mobile web version of the site was used by a decreasing number of people, and we announced that we intended to bring it closer in line to our mobile apps for a consistent experience well before the changeover. We let people preview the new version and solicited feedback, but the problem was i guess we didnt get enough feedback early on (i guess some people didnt bother trying until it actually switched too). There was also some internal pressure due to the looming google changes where we heard that they would penalize us if we didnt have a proper mobile web experience.
Needless to say, while we think a lot of things went well, it didnt go as smoothly as we hoped, and as I mentioned, we certainly aren't perfect but we're definitely learning. The real issue is that we're a very small team and while we can afford to have two versions of the main site, we cant do that for everything (it would just cascade out of control for every change) - so we had to pick and choose what we could tackle. We walked out of the planning meetings saying, "okay, we know that we cant maintain both, but if we're going to do this, we need to get user feedback and act quickly." But the biggest takeaway there was that when we migrated to the new mobile web, it took us longer than we expected to roll out the fixes that people were asking for. That speed and sense of urgency is critical and in hindsight, we needed to be more agile about rolling out fixes (even if temporary) quickly to get users what they needed.
After the fact, (and even ongoing) we had a good internal discussion, asking the same questions i listed above, and had a retrospective to ensure that we work faster at incorporating people's requests and feedback.
There's nothing here!