(nytd 2008-2010)
I believe the Holy Three are Python, Go, and Java. Personally the fact that Go is on there totally invalidates the list for me. It upset a lot of other people, too, because it's not very widely used in the org and is just a pet favorite of one of the higher ups. Was a serious source of friction.
For what it's worth, I agree with almost everything else you said.
I really do hope they streamline a bit of the bloat in tech. It's a real shame. So many dev hours wasted in meetings. So many PMs who know more about the intricacies of Kanban and JIRA ticketing but nothing about the product. There's a lot of talent there, though. I think it can be done.
You asked for it. :) If any of these are inappropriate for you to answer, I understand. Thanks much in advance:
1) The Innovation Report came out in 2014. Per the article (and corroborated by other things I've read), it changed attitudes at the Times because "You couldn’t read that report and think that the status quo was an option." People there still thought the status quo was an option as late as 2014! Is it just standard incumbency psychology - where the incumbent power in an industry lives in an echo chamber, is tied down by vested interests, and can't see change coming - or is something else going on?
2) I've read a few internal reports, leaked and released. All repeat how great the NY Times is -'the best in the world', 'the greatest', etc. - over and over. It was in the Innovation Report, which was supposed to be only for top management to read. These reports aren't marketing to the public (and NYT marketing doesn't use that message nearly as much as the internal reports I saw) and these aren't stated missions ('our goal is to be the world leader in ...'); it looks like flattery in internal communications. It seems like an odd bit of narcissism. What about the culture requires them to tell themselves how great they are? Are they that insecure? Usually highly successful organizations don't need to say that to each other; they know. OTOH, maybe my sample size is too small and it's not really an issue.
3) It still seems to me that they are still a newspaper (emphasis on that old medium, paper) making accommodations to the electronic medium, rather than a news publication on the Internet. Stories still are told almost entirely in text, which was a limitation of the old medium but not the new, and images and video usually are decoration rather than a primary means of story-telling. Even two-bit bloggers will, rather than describing something, just show it to the reader: 'The building is rundown: <img>'. I read a story that described how some innovative high school dance program started class each day with (a dance and song?) - why not just show me a video? Occasionally they have helpful graphics, but they talk like that's a special event rather than a norm of the medium and usually it's a separate story - 'the graphics story' - they can't seem to tell a story integrating different mediums as needed. What is going on? Are they just stuck? Will they let go of the old medium before it's too late?
EDIT: A few edits
I much prefer the largely text medium, even in the digital age. One can consume & process content immensely faster with text than inages and video.
I prefer whatever is more efficient too, and text is great. For example, generally speaking, I prefer text to a video that is longer than maybe 30 seconds, because reading is random access and I can skip to what I want.
But as a universal statement, I'm pretty sure the above comment is factually inaccurate. Certainly for large classes of information, visuals are more efficient. For example, a graph of year-by-year unemployment rates in the 20th century is far more efficient than a list of numbers and years. Similarly, a photo can convey information that would take pages and pages of text.
Graphs are also extremely specific, and very easy for people to misinterpret/get misled by. The specificity of graphs also means that most forms of information cannot be conveyed that way, and so it is a limited tool.
The NYT does incredible work. It just needs to take a hard look at it's digital side and trim a lot of the fat. There's a lot of churn and little long term vision. Unfortunately layoffs / firings are rare in the tech org but buyouts and their ilk are widespread in the newsroom.