Nobody wants to be followed up with. Treat the follow-up as your cue, and make the touch leave the other person better off.
The idea
Do you want to be followed up with? Almost never. A follow-up only drags something back to someone's attention. Adding value means their life is a little better after they hear from you. In my coaching this was the first of our five fundamentals: a follow-up is the trigger, adding value is what you do. The reframe also takes the sting out of the fear. You stop worrying about being the desperate pest "just following up" and start asking what you can give. And the more value someone gets from you, the more mindshare you hold, and the slower it decays.
How to do it
When a reminder, a meeting or a calendar nudge says it's time, treat that as your cue to find something worth sending.
Ask what would make this person glad they heard from you: a detail they mentioned, an intro, some useful information, a gift.
Size it to the relationship. A "just thinking of you" counts. So does a gift.
Send it. Doing nothing is the least value you can add.
Example
Years ago I was recruiting a senior candidate who wasn't looking. We met at a cafe in Virginia on a perfectly frigid morning and agreed to "keep in touch." On the way out he mentioned his son was playing in a free-throw tournament. I wrote it down. Back at the office I started the standard thank-you email, closed it, and shipped him a basketball from Amazon with a short note. A week later he wrote back that his son used it every day, and introduced me to a respected marketing executive he'd known for 12 years. Small talk, good notes and $10 of rubber.
Watch out for
Don't let "value" turn into paralysis. The barrier to showing you care is absurdly low.
Ask whether the gift really needs your logo, or whether you are turning them into a walking billboard.
Meaningful, Relevant, Valuable: Check every touchpoint, gift or event three ways: will they remember it, does it connect to what they care about, does it actually improve their life?
The Five Fundamentals of Adding Value: Five rules from my coaching: follow-up is the trigger and value is the act, never do nothing, focus on the feeling, invest by priority, extend your personal monopoly.
Something Is Better Than Nothing: Any touch they can attribute to you beats silence. If you don't know what to say, say anything.
CAPITAL: Add Value: The second A in CAPITAL. Make each touchpoint meaningful, relevant and valuable, size it to the relationship, and deliver it personally, by connecting, by hosting or by broadcasting.