? Ask Paul: December 26 ⭐

Happy Friday and Happy Holidays! Here’s a short-ish edition of Ask Paul for this short week and extra-long weekend.
? The outlook for Outlook
Christian-Gaeng asks:

Since the Outlook team wants to relaunch the development of the new Outlook around AI, are there any indications that the classic Outlook will remain available beyond 2029? I can't imagine that large corporations will switch to a new Outlook with AI at its core.

So many thoughts.

The first of which is that there is almost nothing I dislike more than Outlook in all its forms. But most especially the classic desktop app that some can’t bear parting ways with for some reason. The new Outlook is a sort of gift that keeps on giving if all you want is drama because there will always be some feature that one person finds indispensable that isn’t in the new app, and we can just complain about it endlessly. It fills the gap nicely between other dramas real (Crowdstrike) and imagined (Recall).

But the combination of the new Outlook and AI? Oh. Chef’s kiss. That’s the unholy nexus of Hell right there. It’s almost too perfect.

Outlook has thus far weathered two major shifts: Internet email, which arrived just as Microsoft released the first version of the app, and chat-based collaboration as popularized by Slack. In the latter case, Microsoft of course created Teams and has seen incredible success, but it also did that classic Microsoft thing and didn’t leave Outlook users behind by figuring out ways for them to stick with their tool of choice and interact with those who were on the new thing. Also, the whole “One Outlook” thing makes sense in that having a single codebase for add-ons across all app versions is obviously the right choice. (Cue next round of complaining about web apps.)

Quick side-trip: Thinking about this, it’s pretty clear that the technology behind Loop is/was the connective glue that makes all that work. And that in the pre-AI era, we were suffering through a similar volume of regular updates all tied to Teams. Pre-pandemic, during the pandemic, and then for the first few years after, it was all Teams all the time. From my perspective having to cover the news, AI/Copilot is just the Teams playbook, but amplified.

Obviously, Microsoft is going to integrate AI into the new Outlook. Right? I mean, this is obvious.

As obvious, Microsoft is not going to integrate AI into the classic Outlook. This can be viewed cynically, it’s so easy, but pragmatically (this will come up again and again, I bet) it makes sense. Classic Outlook is essentially if not literally deprecated, and it will get security updates, but it also has an end date. Though there is arguably some precedent for thinking otherwise if you’re familiar with the history of OneNote, Outlook is too big and too central to the whole Microsoft 365 productivity story to co-develop two versions of this app for the desktop. There can be only one.

Another side-trip: Complaining about the new Outlook...