Calendar AI hasn't solved my problem (yet)

I’ve been thinking a lot about AI tools in meetings, probably due to lingering discontent with the reinforcing feedback loop of platform decay.Footnote 1Cory Doctorow, “How monopoly enshittified Amazon” (opens in new tab) (archived Jun 2026). For example, Apple was just announced to have acquired an AI calendar appFootnote 2iOS 19 could bring AI to the Calendar app per just-revealed acquisition (opens in new tab) (archived Dec 2025) (9to5Mac). that will surely reappear at tomorrow’s WWDC, Copilot offers lots of calendar integrations, and a quick Kagi search reveals dozens more AI-enabled assistants that promise to book meetings faster, handle conflicts automatically, and generally optimize my work day. But I don’t think these tools are solving the right problem for me!

First, I don’t want a digital assistant that makes it easier to manage meetings, I want one with sufficiently aligned autonomy to know when not to have one in the first place.[As a leader, you can fact-find in many ways, each with effects of different magnitude on system equilibrium. Calling a meeting is an official act that signals a certain blunt-force finality, and these optics change how participants think about, talk about, and do the work you want to discuss. This is a useful foil to the “see risk, book meeting” strategy that you’ll often see deployed on autopilot. Plus, over-communication is a failure mode.Footnote 3Amazon, Teams and interactions (opens in new tab) (archived Jul 2026). And second, these AI applications make it easy to book meetings just in time,Footnote 4Lean manufacturing (opens in new tab) (archived Jun 2026). so it looks like they solve a critical bottleneck for the people in 30+ hours of meetings every week. But The Principles of Product Development Flow offers a fun counterargument:

… it is important to go beyond the popular but simplistic idea that the capacity of the bottleneck controls system flow. In fact, flow through a bottleneck is affected strongly by the process that precedes the bottleneck. The upstream process determines the variation in the arrival rate at the bottleneck, and this affects the queue. Managing the process upstream of the bottleneck is a valuable tool for improving flow at the bottleneck.

So we shouldn’t merely stop at the meeting bottleneck, but rather look upstream for higher-leverage process improvements. And what’s upstream of a meeting request? Precisely all the unspoken, unwritten context that’s hard to feed an AI assistant! For instance, it might not capture the preference falsification (opens in new tab) inherent in business relationships or the adverse selection caused by the resulting social capital dynamics;If you’re honest with yourself, you probably don’t want to meet with everyone who wants to meet with you! And the converse holds too, if you’re being extra honest. how many “could’ve been an email” meetings you’ve been party to recently; situations where your counterparty hasn’t Read The Manual; or times where nobody’s really sure why there’s a meeting in the first place. This is all stuff I think about sometimes, but how do I get the AI assistant to recognize it?

While we wait for AI to catch up, what I’d really like is a RothianFootnote 5Alvin E. Roth (opens in new tab) (archived Sep 2025). clearinghouse that matches meeting requestors with subject-matter consultants.Footnote 6See “What Have We Learned From Market Design” (opens in new tab) (archived Dec 2025). This would thicken the market so that I can delegate effectively; it would enable deferred-acceptance matching schemes, which are strategy-proof and therefore improve business transparency; and it’d even allow batch-accepting invites so that nobody has to reprioritize whenever someone higher on the org chart needs to squeeze in a new meeting.Footnote 7The convenience of the marginal meeting time slot is strictly negative. People pick the best times first, so last-minute stuff either lands on Fridays at 4:30 pm, or you’ve got to reshuffle your entire calendar to free up time earlier in the day. The high-order shock wave this sends through the org’s calendars actually is a legitimate use case for an AI calendar assistant, but even so it’d only treat the symptom. We’ve basically independently recreated the sprint, but for meetings!

If in some distant future you’ve vibe-coded your way into founding a B2B SaaS company based on this idea, all I ask is that provide a requisite shoutout on your About page!