Marc Spector (Associate Producer for Shep at WOR from 1974 to 1974) writes:

Did Jean spend hours preparing the show or did he write a couple of words on a scrap of paper on his way into the studio? The answer is really: both of the above. Jean lived his show--it was really him. Therefore, his prep was just living and remembering and recalling things from decades or minutes before the 10-inch machine started rolling. But, in truth, the latter was what really happened. I remember Jean asking me what I thought of something right before we walked to the studio. He would write my answers down on a scrap of paper and that would be the basis of the show. He would do the same with the studio engineers who he used regularly for such material. He wanted to make sure the show was about what real people wanted to hear--not ivory tower stuff. It was his blue collar background, I suppose. Most of those guys really never 'got' Jean but they played along. Only a couple, like Herb Squires, really knew they were a part of something very special.

The show was absolutely, 98% unscripted. Don't let anyone tell you otherwise. Jean could never have done what he did with a script. He wasn't a radio star - he was a monologist. He loved to talk about what was on his mind - although it was 1974 and still a very G-rated broadcast world. As for the clock - it was my job (or Leigh's if she sat in on the session) to keep Jean informed of the time remaining for the show. This was a VERY important component of the job. He wanted a '5 minutes remaining' visual and one a bit sooner (although I cannot remember if it was 2 or 3 minutes). He would seamlessly and flawlessly (most of the time, anyway) wind it down to perfection right at the close of the theme. Listen carefully to how far out the show would be just 2 minutes from the end and how it wound up so perfectly only 120 seconds later. He was good. I will say, though, that we did mis-time a couple of shows while I was there. Ended it a minute early. Big problem. Oh, well it could have been too long which would have been a bigger problem. While I did the show, it was most often broadcast in a 9:15 slot. As you know, WOR did a 15-minute live newscast from the studio across the hall every hour up until the beginning of our show. I do believe that this (the 9 PM show) was the last live news show of the day and that they did not do one following our show, so timing was really important as they had no live announce to make up for errors. WOR did broadcast an hourly BEEP and shows ended right on that beep. The News would immediately follow the BEEP. Anyway, the mis-timed show was a rare event but it did happen.