One of the challenges of building a network is finding ways to maintain meaningful conversations with the people you might. My solution to this is to plan ahead, to be opportunistic about opportunities to reconnect, and tto be empathetic enough to guess at what that person might be struggling with.
On to the list . . . .
1. "How did [that thing that is important to you] turn out?"
The idea is to follow up with someone at around the time you expect something big to be happening in their world. This requires careful listening and good notetaking but it's way more meaningful then emailing them along with everyone else they know when they post some big news on LinkedIn (or wherever) after the fact.
Pro tip: When you are talking be on the look out for comments like: "We're hoping to launch our API in January" or "The project I'm consulting on is ending in a few months and I'll be thinking of my next move around then" or "I'm working on something that will hopefully close by the end of the summer".
2. "It'd be great to compare notes."
The thought here is to look for something that you and they are both doing - for example, advertising in a certain channel or creating analogous partnership models - and suggesting that you learn from each other. This requires paying attention to their world and being thoughtful about their potential challenges so it's a tough one. It's worthwhile, thought, since sharing and learning creates real bonds.
3. "Saw this event and thought it might be interesting for you."
In New York there are at least a half dozen weekly newsletters listing dozens or hundreds of events a week. While they're clearly doing everyone a real service by consolidating those notices into a digest, even the digests are tough to keep up with. Giving one or more of the newsletters a close scan always yields a couple nice and useful nuggets for people I've met. Even better is when you spot someone's name or company in one of the notices; great to email them and say "Whoa. Big time!"
One to avoid: "Hey, did you see that your main competitor just went public?"
While sharing industry news can be valuable, sharing this sort of news really isn't. You can be fairly certain that the person you're emailing has heard this tidbit and you're putting them in a tough position in terms of how they can respond. They're not going to reveal their company's funding plans and nothing good will come of them commenting on the competitor's decision. It's kind of like telling someone that their ex-boyfriend or girlfriend just got married. How do you respond to that?
And another: "Just wanted to say hi and see what's up."
Totally and utter waste of everyone's time.
Follow me on Twitter: