Every inbox has two kinds of finished conversations. The ones that ended because they were done, and the ones that ended because you stopped writing. They look identical. Nothing in your inbox marks the difference — which is why the second kind quietly piles up.
This finds the second kind. It takes about ten minutes, and you do not need to install anything or know what an API is.
You need the threads in front of Claude. Pick whichever is easiest for you:
- Email: connect your mail account to Claude, or export the last 90 days as a file and drop it into the conversation.
- Instagram or LinkedIn DMs: open the twenty or thirty most recent conversations, copy them, and paste them in. Yes, by hand. It is ten minutes once.
- A spreadsheet you already keep: even better. Drop the file in.
What a right answer looks like: Claude tells you how many separate conversations it can see. If it names a number, you are ready.
Where this goes wrong: if Claude says it cannot see any files, you are in a browser chat window rather than a session with access to your stuff. Open the folder or connect the account first, then ask again.
Say this, in these words:
Go through every conversation here. I want a list of the ones where the other person wrote back at least once, and then the last message in the thread is mine, and nothing has happened since. For each one give me: who it is, the date of their last message, what they actually said, and how many days of silence there have been. Sort it by the longest silence first. Do not write any messages yet.
What a right answer looks like: a short table. Names, dates, their words, a day count. When I counted mine, there were fifteen.
Where this goes wrong: if you get back a general summary of your inbox instead of a list, the word that is missing is list. Ask again and say the word.
This is the part you do not hand over. Go down the list and mark each row as one of three things:
- They asked me something and never got an answer. These are not follow-ups. These are debts. Pay them today, and apologise for the delay without explaining it.
- They said yes to something that never happened. Write one sentence that offers the thing again, with a date in it.
- It genuinely ended. Plenty will be this. Close them and stop thinking about them.
What a right answer looks like: most rows land in the third bucket, and that is fine. The whole point is the handful in the first two.
Where this goes wrong: letting Claude write the messages for you. It does not know what you promised, it will sound like a sequence, and people can tell. The list is the machine's job. The sentence is yours.
This is not a follow-up system, and it is not discipline. Discipline is what everyone recommends and nobody sustains. This is a list you can regenerate in one question whenever you want to know where you left people — which is a different thing, and it works on the days you are not at your best.
Written by Conrad Caffier. I keep a file of every DM conversation I have running. When I finally counted it, fifteen of the people who had written back to me were waiting on me — including one who had asked a direct question and never got an answer.