To begin with, Signet would do a lot of the heavy lifting: contact the recommenders for the awards, find out which events the candidates will probably be at, and track the schedule of who should get what when. We set up a shared folder in Google Docs (which turns out to be a great tool for this sort of thing), with one master spreadsheet of the tentative overall schedule, and one spreadsheet per event of the awards we really expect to do. These per-event spreadsheets would typically get finalized about a week before the event, at which point Signet would send an email summarizing the list.
Once the email went out, we (the heralds) would put together The Cards. Everything ran based on decks of 3x5 index cards. We set up a simple template in Word: each card was essentially a copy of the row in the spreadsheet, including the person's name, the award, a few brief notes reminding who they are and what they've done, and the scroll information. We also added cards for things like expected presentations, quests and other items of business, as well as the two cards that were always included: Welcome Newcomers (which was a high priority this reign) and Thank Musicians (which was always included, although only relevant about half the time).
In parallel with this, tpau, in her capacity as Keeper of the Big Bling Box (a large tackle box full of little comparments holding different medallions and tokens) would take a look at the spreadsheet, and make sure that the Little Bling Box (which actually went with the Royalty) had any medallions that might be needed. (In practice, most Orders have someone pass on a medallion, but we ran on the assumption that we might need to provide everything.)
We would then print two copies of the card deck, one for the Heralds and one for the Royalty. I would prepare a proposed order for the docket along the lines that TRM prefer, typically an hour or so before Court. (Multiple "acts" punctuated by the big awards, for better dramatic tension.) They would review and tweak that to get the final docket; at that point, we would go through both decks, all of the scrolls and all of the cutsheets, and put them into matching order.
The Royal copy of the cards would go into the Little Bling Box between them, so they could keep track of what was coming up next. (Ideally, they would get this deck in advance, so they could review the docket while traveling, but that didn't always happen.) The Herald copy would be given to one of the chancery heralds standing behind the thrones (usually tpau or hfcougar). She would have the cards and a pen. Going in order through the stack, she would hand the next card to the Herald, who would do the item of business and hand it back; she would then number it. If things went askew from the expected schedule, we would shuffle the card to later in the stack. (We also tried to usually have a few blank cards, in case something came up in the middle of Court.) The numbered cards then got transcribed, after the event, as the Court Report. (For particularly long Courts, we occasionally printed a third copy of the cards, so that the Head Lady in Waiting could use it to pace the retainers.)
All in all, it was a fair amount of prep work (and OMG we went through a lot of index cards), but the process works quite smoothly, and is relatively tolerant of things shifting in mid-Court. By taking the tracking-what-happened job off the shoulders of the Herald who is actually yelling, it allowed us to be a hair calmer in Court (not quite as many things to keep track of). It takes some discipline, but so long as you set aside enough prep time, it's a good model...