Use moments in their life, from new jobs and kids' milestones to illness and loss, as reasons to reach out between your regular check-ins.
The idea
Between your regular check-ins, things happen in people's lives, and each one is context for reaching out. There are the recurring dates (birthdays, anniversaries, the anniversary of buying their house), the one-time occasions (promotion, new job, a baby, a bar mitzvah), news about them or their company, and the hard stuff: a death in the family, an injury, a divorce. Don't only show up for the good news. People are often loneliest when they're struggling, and that's exactly when business talk should be off the table.
How to do it
Decide which kinds of events you genuinely care about. Track those.
Follow your top people on the platforms they actually use so you hear the news.
When something happens, reach out personally.
For hard times, leave business out of it entirely.
Example
I've updated my thinking here. The book says to remember birthdays and anniversaries. Now I'd tell you to track only what you care about. A birthday message from someone who couldn't care less about birthdays is noise. I've caught myself nodding along about F1 races and IPOs, completely lost, because I'd somehow made someone think we shared that interest. Exhausting for me, mechanical for them. After you meet someone, ask: what do I want to remember about this person in a year? Track that.
Watch out for
The pile-on. Big news brings a flood of social media activity, and your note can become one more drop in it.
Crisis Outreach: In hard times, say you're thinking of them, don't ask for updates, and make a specific offer instead of "let me know if you need anything."
The Happy Almost-Birthday: If you're someone who likes celebrating birthdays, send your wishes the day before, when you aren't one of 200 messages.
Time-Shift Your Congratulations: When someone changes jobs, send the congrats and then add the notes nobody else sends, one month in and again at one year.
The Social Media Signal Review: Set a two-minute timer, scroll one app looking only for real life updates, then close it and reach those people off-platform.