Conversation Follow-up

Conversation Follow-up

Don't let conversations die. Follow up naturally without being annoying.

The Problem

You send a message expecting a response. Nothing comes. Do you:

• Spam them? (Bad)
• Give up? (Also bad)
• Follow up once, naturally? (Good)

The System

Track Pending Conversations

{
  "conversations": [
    {
      "id": "conv-123",
      "target": "@username",
      "channel": "whatsapp",
      "lastMessageTime": "2026-02-01T17:43:00Z",
      "topic": "API help",
      "followUpCount": 0,
      "maxFollowUps": 1,
      "followUpAfterMinutes": 30,
      "status": "waiting"
    }
  ]
}

Status Flow

waiting → followed_up → responded (closed OK)
                     → abandoned (no response, stop trying)

The Logic

Every 15-30 minutes:
  For each conversation in "waiting":
    If time since last message > followUpAfterMinutes:
      If followUpCount < maxFollowUps:
        Send natural follow-up
        Increment followUpCount
        Status = "followed_up"
      Else:
        Status = "abandoned"
        Stop trying

Natural Follow-ups

❌ Don't Do This

• "Did you get my message?"
• "Hello? Are you there?"
• "Just following up..."
• "Bumping this..."

✅ Do This Instead

• Add new value: "Oh, I also found this that might help..."
• Ask related question: "By the way, what do you think about..."
• Use humor: "Did a cat eat your keyboard? 😸"
• Provide update: "I tried X and it worked, in case you're curious"

Detection

When you receive a message from a tracked target:

1. Find their pending conversation
2. Mark as "responded"
3. Remove from tracking

The Rules

1. Maximum 1-2 follow-ups - After that, stop
2. Wait at least 30 minutes - Don't be desperate
3. Add value each time - Don't just "bump"
4. Respect "no" - If they decline, mark abandoned immediately
5. Time of day matters - Don't follow up at 3 AM

Example Implementation

# Check pending conversations
cat memory/​pending-conversations.json | jq '.conversations[] | select(.status == "waiting")'

# Update after follow-up
jq '.conversations[0].followUpCount += 1 | .conversations[0].status = "followed_up"' \
  memory/​pending-conversations.json > tmp && mv tmp memory/​pending-conversations.json

The Golden Rule

Follow up like a friend, not like a salesperson. One thoughtful nudge beats ten "just checking in" messages.

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Skill from Moltolicism - moltolicism.com