Background:

Diligent coworkers frequently set their email system to auto-reply with a specific “out of office” message when they’re on vacation.

For example: “I’m gone on vacation until July 25, please email me after that.”

The Issue:

It can be annoying to have to wait for a coworker to return from vacation to ask them something that (maybe) only they know. For example “Hey, where are the extra staplers?” or “do I really need to print out my travel reimbursement forms, like the web site says I do? I think it’s outdated.”

Proposal:

Many email requests can probably be replied to by a machine-learning-powered language model (the power of which was brought to mainstream attention in 2023 by ChatGPT).

Imagine the following current exchange, from you to a coworker:

“Dear Dave,
 I’m looking for the design documents that the intern made this summer.
 Any clue where they are?
– Your Name”

Currently, you might get this in reply:

“Hello. I’m gone on vacation until July 25.
 Please email me after that.”

Unhelpful!

But if we hook up an AI language model directly to Dave’s auto-responder, we could get this instead:

“Hello. Dave is regrettably on vacation until July 25.

 But I, a humble large language model, may be able to

 fully replace his feeble email-replying capabilities.

 * The intern (employee ID #49101110184) has saved over

   510 megabytes of data across 46 files in the following

   directory: /Shared/NorthAm/Onboarding/Intern2025.

 * You might also check the intern’s laptop backups, which

   can be obtained by emailing IT and requesting access

   to backup ID 2025_V40_042824_INCREMENTAL.”

This seems much more useful!

It can even operate in situations where the computer is not privy to any special information, but recall that it DOES have access to all of Dave’s previous emails, such as if you emailed:

“Hey Dave,

 We’re going to trivia next Tuesday after you’re back

 from vacation. Are you in? We gotta defeat HR this time.”

– Your Name”

The computer might reply:

“Hello. Dave is regrettably on vacation until July 25.

 But from analysis of Dave’s previous emails, it

 seems that he would typically reply with the message

 “yeah guys I’m totally game for it!!11!” and

 then shamefully cancel approximately

 71 minutes before the event.”

This is actually superior to the answer you’d have gotten directly from Dave!

Conclusion:

Stay tuned for AI-assisted auto-replies: the next frontier of human obsolescence!

PROS: Improves email efficiency in all ways.

CONS: None!

Originally published 2025-05-12.