The smallest possible touchpoint, and the one I've seen work best: 'Hey! You came to mind this morning. Hope you're doing well!'
The idea
I used to think maintaining a relationship meant loads of research, Cutco knives and courtside seats. Tasshin's guide to friendship calls the simpler move a "smooch": a plain "just thinking of you." Hollywood agent Ari Emanuel sends "Can I help? All good? You need anything?" to hundreds of contacts a day. Four or five years ago I'd have called that too simple to work. I'm a convert. Even the slightest "I care about you" speaks to everyone's deep desire to be seen, and it has generated an incredible amount of business for my clients.
How to do it
Open your texts, call history, LinkedIn messages or sent email.
Scroll down a few pages until you hit someone you had a good connection with but haven't talked to lately.
If you have something specific to say, say it. If you draw a blank (most of us will), send the script.
Send three.
Example
Picture your phone buzzing mid-inbox with the name of someone you had a great coffee with months ago: "Hey, you just came to mind this morning. Hope you're great!" Feels pretty good. Yes, this works on business contacts too.
Script
"Hey! You came to mind this morning. Hope you're doing well!"
"Hey! You popped into my head today. How are you?"
"Thinking of you. Hope all's well!"
Watch out for
Sending the same line to your whole list every month. Space it out per person.