End check-ins with "no need to respond." Taking away the obligation makes people feel cared for, and they reply more often.
The idea
"I would love to hear the latest update!" Few lines fill me with more dread. It's homework. Any message that expects something back puts weight on the other person, and obligation is the enemy of enthusiasm. So drop the weight: add "no need to respond" (or just NNTR). You're telling them the thought was the whole point. Ironically, people reply more, because now replying is a choice. And the replies you do get tend to be better.
How to do it
Write your check-in, share or update.
End it with "No need to respond" or "No reply needed."
Sprinkle in something about you, so they have something to answer if they want to.
Example
My friend Scott was getting crickets from his business contacts. Over coffee we read his messages: all well-meant, all asking for updates or feedback. He switched to sharing something useful, like an article or a quick tip, ending with "No reply needed, just thought you'd find this interesting!" The replies started coming, many of them asking how he was. Tony Cappaert, my Contactually cofounder, ends about half his check-ins this way and says it's like magic.
Script
"Hey, just thought of you this morning. Hope all is well. No need to respond."
"No reply needed, just thought you'd find this interesting!"
Watch out for
Using it on a real ask. If you need something, say so and give them an easy out instead.
Bonus in the AI era: a bot would never volunteer to reduce engagement, so NNTR also reads as human.