It's a little more than that; it also incorporates silence detection so that it waits for the caller to finish talking before 'Lenny' plays its next line.
It does seem natural that it is a recording with silence detection. What about the process of choosing these specific set of dialogue? It is definitely not chosen arbitrarily as lenny's response blend pretty well with marketer's question. I was imagining some analysis on marketer's most used conversation were done.
The lines are exactly the same for each caller, played in the same order, on a loop. The recordings are obviously tailored for telemarketer scripts, and to string them along and make them think a conversation is going, but there's no dynamic analysis going on.
If that's what you're saying, I apologise for misinterpreting!
https://toao.net/595-lenny
https://www.youtube.com/watch?v=lryrm2CVaVg&list=PLduL71_GKz...
https://www.reddit.com/r/itslenny/