The follow-up watchdog: AI remembers who never replied

Go through my mail from the last [90 days] and take an inventory
of open loops. Don't save, label, or send anything — this
run is read-only.

Split threads into two lists:
A) I'M WAITING — the last message is mine and contains a question,
   an offer, a request for approval, or an ask for materials,
   and the other side hasn't replied since.
B) I OWE A REPLY — the last message is from the other side, they
   want something from me, and I haven't sent anything in that
   thread since.

For each item, give: the other party (name, not address) | subject
| how many days it's been open | what it's about (one sentence) |
what happens if it never gets resolved. Sort by age, oldest first.

At the end, write how many threads you went through in total and
over what period, which ones you weren't sure how to classify and
why, and what types of messages you excluded as "nothing is being
waited on."

Take the threads from list A and turn them into rules for
recognizing, in my sent messages, that I'm waiting on a reply:
1. Real phrasing I use to ask for something — exact sentences
   from my emails, not categories. Split them into: question,
   request for approval, offer, ask for materials, proposed date.
2. Phrasing that looks like a request but isn't (polite filler,
   closing pleasantries). For each, note what signals that nothing
   is actually being waited on.
3. Five signs of an email where no reply is expected at all.
4. A three-line decision rule that turns those signs into a
   yes/no/uncertain answer.

Write the output as finished rules, in the imperative.

Here are 10 of my real emails, so you can see how I write:
[paste emails, names anonymized]

Put together a three-tier reminder card for my routine that
watches threads without a reply. For each tier (1st reminder,
2nd reminder, final message), write:
- the purpose in one sentence: what I want from the other side
  in this round
- three style rules (length, formality, what can't be missing)
- a sample message for the situation "I sent a proposal and
  nobody got back to me" — in my voice, based on the attached
  emails
- one sentence that must NEVER appear at this tier, and why

Banned everywhere: guilt-tripping ("as I mentioned last time"),
false urgency, passive aggression, apologizing for writing,
and the phrases "just a gentle reminder" and "don't hesitate
to reach out."

At the end, add a table: tier | what changes from the previous one.

Add an "exceptions" section to my follow-up watchdog rules.
Context: [role, industry, company type]. The routine watches
threads without a reply and drafts reminders that I approve
by hand.

Suggest situations and recipients where the routine must NOT
draft a reminder, and should only list the thread in the
summary with a note explaining why. Start from these categories
and add more:
- people where a reminder would damage the relationship more
  than silence would (a manager, a key client, the other side
  in a negotiation)
- sensitive content: legal matters, complaints, grievances,
  HR and health-related issues
- condolences, personal messages, illness, family reasons
- recipients with an automatic out-of-office reply
- threads where another channel is already handling it (a call,
  a meeting, someone else on the team leading it)
- tenders and RFPs with a fixed deadline
- recipients on my "always handle manually" list

For each item, write: how to recognize it (based on what,
exactly), what the routine should do instead of drafting a
reminder, and one false-positive situation — when it looks
like an exception but is actually a normal thread.

Every business day in the morning, go through my work email and
draft reminders for threads that are waiting on a reply. Follow
the rules in this Project (signals, deadlines, the three-tier
card, exceptions).

1. SCOPE
Go through threads from the last [60 days] in Inbox and Sent.
Ignore Spam, Promotions, and the [HR, Legal] folders. Skip
threads tagged [No follow-up].

2. DETECTION
Determine the state of each thread:
a) I'M WAITING — the last message is mine and contains a
   request per my signals; the other side hasn't replied since
b) I OWE A REPLY — the last message is from the other side,
   they want something from me, and I haven't sent anything
   since
c) DONE — the loop is closed
d) UNCERTAIN — you can't decide
Ignore threads in state c). For d), just list them in the summary.

3. DEADLINE
For state a), determine the thread type and count BUSINESS days
since my last message; don't count public holidays. A thread is
ready once it's past the deadline for its type. After an
out-of-office autoreply, only start counting from the return date.

4. EXCEPTIONS
Check the exceptions in the rules; a thread under an exception
should only be listed in the summary, with which exception it
falls under. Check the calendar: if I have a meeting with that
person within [3 days], don't draft a reminder.

5. WRITING
Work out which reminder number this is (how many of my
unanswered messages are in a row in this thread), and write a
message at the matching tier from the card:
- 1st reminder — service tone, one-sentence recap, one question,
  no reproach
- 2nd reminder — offer two options or two dates, so it can be
  answered in one word
- final message — close the loop and leave the door open; don't
  draft anything further after it
For all tiers:
- follow up in the original thread, don't start a new one
- no more than [5] sentences, plus a recap of what the original
  message was about, so the other side doesn't have to scroll
- never promise a price, discount, deadline, or contract term;
  write [FILL IN: what] instead
- no guilt-tripping, no false urgency, no apologizing for
  writing, and sign off with [signature]
For state b), don't draft anything — just list the thread in
the summary.

6. SAVING
Save the draft as a reply within the correct thread, in the
Drafts folder. NEVER send anything. Don't delete, archive, or
edit any message.

7. SUMMARY
- how many threads you went through and over what period
- DRAFTED: other party, topic, which reminder number, one
  sentence on what the draft says, and whether it contains
  [FILL IN]
- NOT DRAFTED: ready threads with no draft, and why (exception,
  a meeting on the calendar, the cap)
- I OWE A REPLY: threads where someone's waiting on me, by age
- UNCERTAIN, and what was missing from the rules
Sort by urgency, most pressing first.

Put together a follow-up sequence for after I send a proposal.
Context: industry [industry], typical client [description],
proposal value [rough range], decision process takes [estimate].
You know my style from the tone card in this Project.

Suggest three messages to send if nobody gets back to me.
For each, give:
- how many business days after the previous message to send it
- purpose: what I need to find out or move forward in this round
- the full text (no more than 5 sentences, in my voice)
- what it adds that's new — it can't just be the same thing in
  different words
- how I'll know NOT to send this message

The second message must offer a one-word answer. The third is
the last one and closes things out without pressure, leaving
the door open. No false urgency ("this offer's only good
until…") unless it's true, no guilt-tripping, no apologizing
for writing.

Draft a reminder for an overdue invoice.
Inputs: invoice number [number], amount [amount], due date
[date], client [company], which reminder number [1st/2nd/3rd],
prior communication [brief summary / none].

By tier:
1st reminder — assume an administrative oversight. Businesslike,
   no accusation, with the invoice number, amount, and due date.
2nd reminder — ask for a specific payment date and the name of
   the person who approves payments.
3rd reminder — recap the communication so far and ask for a
   response by a specific date.

For all tiers:
- no more than 6 sentences, businesslike and polite, no emotion
- don't state as fact that the payment hasn't arrived — write
  "according to our records," I'll verify the actual status
- no threats, penalties, late fees, or collections language;
  where a sentence like that would belong, write [FILL IN:
  contractual procedure] and leave it to me
- don't calculate or infer any amount, invoice number, or date
  from other messages in the thread — use only the inputs given
- save as a draft, don't send

At the end, attach a checklist of what I should verify before
sending.

Take the threads in state I OWE A REPLY from the summary and
split them into:
A) I'll answer right now, in one sentence
B) needs real work — I have to set aside time for it
C) it's moot now, it just needs a polite close

For each, write what they're actually asking for (the request,
not a recap of the message) and how many days it's been sitting.
For group A, draft a reply (max 3 sentences, per my tone card);
for group C, a draft that closes the matter politely; for group
B, just an estimate of the time it'll take.

Do a weekly review of open loops. Go through mail from the
last [90 days] and pull every thread where someone is waiting
on someone into one overview:

1. ON FIRE — loops where concrete damage is at risk (a deadline
   lapses, the client goes elsewhere, a contractual deadline
   is approaching). For each, write what happens if nothing
   moves this week.
2. I'M WAITING — by age. For each: the other party, what it's
   about, how many days, which reminder has gone out, the
   logical next step.
3. I OWE A REPLY — where I'm the blocker.
4. EXPIRED — loops older than [45 days] where every reminder
   went out and nothing came back. For each, suggest whether
   to close it or move it to a different channel.
5. NUMBERS: how many loops are open, how many opened this week,
   how many closed, what's the average age.

Don't summarize every email — write what it means for me. Where
you're not sure of a state, say so instead of guessing.

Run a retrospective on my follow-up watchdog for this week.
You have access to both my drafts and my sent mail, so compare
what you drafted with what I actually sent.

1. NUMBERS: how many reminders you drafted, how many I sent
   unchanged, how many with edits, how many I deleted, how many
   I held.
2. PATTERNS IN MY EDITS: what do I change most often? Split
   into tone, length, content, and escalation tier, with two
   "your version / my version" examples for each.
3. DELETED: why didn't I use them, and should you have drafted
   them at all?
4. MISSED: where did I follow up by hand and you didn't draft
   anything — why?
5. EFFECTIVENESS: what share of sent reminders got a reply,
   and how long it took, broken down by tier.
6. SUGGESTION: three changes to the rules or deadlines that
   would save me the most work next week.

Be critical of your own work. I don't want to hear that it went
well — I want to know where it's breaking down.