Most sales follow-ups read as "checking in" or "circling back" — the exact phrases recipients have been trained to ignore. The follow-ups that reopen deals have different structure. Here are the 4 types and the Claude prompts that produce each.
After the first no-response, most reps send the same generic "checking in" or "just wanted to bump this" email. Recipients have been receiving these for years and skip them automatically.
The follow-ups that actually reopen conversations look different: they provide new value, reference a new angle, or change the format. Each has a specific use case.
1. Insight follow-up. "Saw [X] happen — relevant to what we discussed about [Y]." Provides new context.
2. Resource follow-up. "Sharing this [guide/case study/data] in case it is useful — no need to reply." Removes pressure, demonstrates value.
3. Permission follow-up. "Should I stop following up?" Counter-intuitive — often reopens deals because it acknowledges the awkwardness.
4. Specific question follow-up. "One specific question: [X]?" Lower-friction than asking for a meeting.
Insight follow-up:
Write an "insight" follow-up email to [PROSPECT] at [COMPANY] who went quiet after [STAGE].
Last conversation context: [WHAT WE DISCUSSED]
A recent news event or trend relevant to their situation: [SPECIFIC]
Format:
- Reference the specific event/trend in line 1
- Connect it to what we discussed previously
- Offer one specific insight without pitching
- Close with low-friction reopen ("worth a quick conversation when timing works")
Max 80 words. No "circling back", no "wanted to follow up", no "thought of you". Permission follow-up:
Write a "permission" follow-up email to [PROSPECT] who has not responded to 3 prior touches.
Format:
- Acknowledge the silence directly
- Ask whether they would prefer I stop following up
- Make either answer easy ("a 1-word reply works")
- Close with respect, not desperation
The goal is honest engagement, not extraction. Max 50 words.