How to clear out old "Waiting on them" items and leads that are no longer live

You open the Inbox, this screen says "Waiting on them" over a stack of conversations, and a lot of these are old and no longer of use. Some of these are from months ago, from people who never wrote back. How do I get rid of these? One performer called this screen one of his balls of tangled yarn, and that is fair. The answer starts with something the app never says out loud: it is not going to tidy itself.

Nothing ages out, archives, or closes itself

There is no 30 day rule and no overnight cleanup sweep. A lead you stopped working in March is still a live lead next year, and a conversation that landed in Waiting on them stays there until you or Otto records something that changes it. That is on purpose, because the app will never decide by itself that a booking is dead. It does mean tidying up is an action you take, not something you wait for. It is worth more than neatness: every lead still sitting in your Booking HQ is read again on future runs, so a season of dead gigs spends your Claude usage on history instead of live business. Your Claude usage limit: why it runs out, what uses it, and how to make it last tells you to archive old leads without telling you how. This is the how.

The dead end: there is no X on an Inbox row

The first instinct is to look for one. It is not there, so skip that search. A row gives you Open when the conversation links back to the original post and, when a draft reply is still attached, Edit, Open & copy, then I sent it or Not yet. That is the whole set: no dismiss, no archive, no X, no select all. An X you have seen on a card elsewhere in the app belongs to that board only.

An item reads as Waiting on them because its record carries a blocker, which the row spells out on its Waiting on line. It leaves that group when the conversation is recorded as replied, and drops into Handled.

Move a stale conversation into Handled

A row in Waiting on them never has a draft on it, because the moment a draft is saved the item moves up into Reply ready instead. So on these rows there is genuinely no button to press. (If the one you want is sitting in Reply ready, the draft path finishes it: Open & copy, send the reply where the conversation lives, then I sent it.) For a stale item, ask Otto in chat, naming the person: "Mark the conversation with Dana Whitfield as replied. I answered her in March and she never came back." Otto reads the same digest you are looking at, including the file behind each row, so it can find the right one and record that the reply went out. Give the real date if you know it, then press Refresh.

Only ask for that where you genuinely did reply, because it writes into your record. And you cannot make a conversation disappear. Otto will not delete it either, since "never delete the performer's data" is one of its fixed limits at every autonomy level, including Run it. The conversations are plain files in a conversations folder inside your Booking HQ, so you can delete them yourself in Finder or File Explorer, but only if you mean it: the history goes with the file.

Clear out old leads on the Gig Desk by setting the stage

The bigger pile is usually the gigs, and here there is a real control that happens to be hidden. Two of the eleven stages, Show completed and Lost, are the closed ones, and their columns do not appear by default, so on a fresh board there is nowhere to drop a dead gig. That is the mechanical reason a board fills up with inquiries that died last season.

1. In the right pane, click Gig Desk in the tab row. Older versions labelled this tab Leads, and some articles still call it that.
2. Be on the Board view rather than List.
3. At the top right, beside Edit lists, click the chip reading Show closed with a count next to it. The Show completed and Lost columns appear.
4. Drag each dead card into Lost, or Show completed if the show happened and is simply behind you. A confirmation reads Moved to Lost. Saved and verified. with Undo last edit beside it whenever the move can be reversed.
5. Click Hide closed when you are done.

From the List view instead: expand a row, click Edit gig details, set the Stage dropdown to Lost or Show completed, and click Save changes.

A closed gig stops counting as owed work, so it drops off the due list and out of your Today briefing even when it still carries an old follow-up date nobody cleared. What it does not do is remove the record, which stays in your Booking HQ and is still read on every future run. For that, archive it.

How do I archive a lead so it leaves the Gig Desk

There is no Archive button anywhere in the app. Archiving exists, it is safe and reversible, but it lives with Otto in chat. And one detail is easy to miss: Otto archives by the lead's folder name, not the client name printed on the card. Ask it to archive "the Henderson wedding" and it may find nothing.

1. Open the Settings tab and find Your Booking HQ. That field shows the exact folder path on your computer.
2. Open that folder, then leads inside it. Every subfolder is one lead, and its name is what Otto needs. If you would rather not go digging, ask Otto where your leads live and it will lay out the map of your Booking HQ.
3. Ask by folder name, with a reason: "Archive the lead in the folder henderson-wedding-2025. Reason: the date passed."

The lead folder is copied into an archive folder, the copy is verified file by file, and only then is the original removed, with a one line roll-up appended to archive/leads.md. It never deletes. To reverse it, ask Otto to restore the lead in that same folder and it returns exactly as it was.

The card is then gone from the Gig Desk and the record is out of everything Otto loads on future runs, which is the part that gives you your usage back. Two notes. Archiving a lead does not touch the Inbox, because gigs and conversations are separate piles. And if it fails with a permission or busy error, that is nearly always your Booking HQ sitting inside OneDrive, Dropbox, or a network drive whose sync holds the files open, or antivirus scanning it; moving your Booking HQ to a plain local folder clears it.

For a client who books you every year, park instead

For an annual gala or a repeat corporate client, ask Otto to park it: "Park the lead in the folder rotary-annual-gala until 2027-03-01." It stops counting as owed work until that date and wakes by itself when the date arrives. One limit: the card stays visible on your Gig Desk. Parking quiets a lead, it does not clear it off the board.

Is there a "clear everything older than 90 days" button?

No, and there is no multi-select. Every archive and every stage change is one record at a time. The nearest real thing is to ask Otto to show you which leads it would archive: it comes back with a proposed list and never acts on it alone, so you read it and say which ones you agree with. For a year of backlog, turn on Show closed and drag the obviously dead gigs into Lost in one sitting, then ask for that proposal on what is left.

If it still will not clear

If a card reappears after you move it, if an archive reports success but the gig is still on the board, or if Otto cannot find a folder name you can see with your own eyes, open a ticket at booked.kivimedia.co/support rather than trying again. Tell us the folder name, what you asked for, and the exact wording of what came back. A support bundle helps: it is in the Settings tab, scroll down to Generate Support Bundle.

Still stuck? Submit a ticket from this help center and we'll take it from there.