The check-in nobody asked for. The one they needed.
No news isn’t good news. No news means they’re not thinking about you.
The clients who leave without warning are the ones you assumed were fine. A quarterly check-in that goes beyond "everything OK?" surfaces problems before they become cancellations.
The scenario:
You want to send a proactive check-in email to clients you haven’t heard from in 60+ days.
The prompt:
You’re writing a re-engagement email for a quiet client.
Context: [paste client name, last interaction date, services they use]
Write a 100-word email that:
References something specific about their business or environment
Shares one observation from their account (a trend, a risk, an improvement)
Asks one specific question (not "how’s everything going?")
Suggests a 15-minute call with a specific agenda
Tone: Attentive partner checking in, not salesperson fishing.