I want to revise and expand on The Shy Connector, which seems to have become a perennial resource. I was thinking about the kinds of things I have a hard time with and that other people might want help with too. Does this resonate with you, and can you add more?

Creating opportunities for serendipity: I’m choosy about the events I go to because networking can be draining just as much (or more, even!) than it can be energizing. I don’t really go to coffee get-togethers just to hang out. It doesn’t feel natural to me to possibly interrupt someone else’s train of thought for a question or an idea. That said, I often don’t mind overhearing other people’s questions, and sometimes I end up chatting with them about that.

Because it takes a lot to tempt me out of the house, I work harder on creating online serendipity through blogging and social networks. I spend time reading about other people’s interests and sharing my own. It does tend to be limited to the people who participate online, though, which means a tiny fraction of the possibilities.

Starting conversations: You know those people who will happily strike up conversations with strangers they meet on the bus or in an elevator? Totally not one of them. I find it difficult to start a conversation with someone for no particular reason. I prefer to have the excuse of a conference, an event, or a question.

I hardly ever start conversations with new people, but I’ve discovered a handy trick of jumping right in the middle of one. If people have read my blog, or if I’ve read theirs, then we can continue the conversation from those points. If we’ve attended a lecture together, I can use that as a starting point as well. As I do more of this, I might get more used to starting conversations to find out what people know.

I also get around this by pulling people into existing conversations. If I see someone else (usually another introvert!) hovering around the edge of a conversation I’m in, I use body language to invite them closer, and direct a few questions their way. I also hover around the edges of other conversations, which is a great way to not have to start one.

Continuing the conversation past small talk: If I go to an event and end up having one unmemorable small talk surface-level conversation after another, it’s quite draining. I like digging to find what people are really interested in or what they’ve learned, but it’s sometimes a struggle to get people out of the name-job-and-serial-number swap.

I find small talk a little easier for acquaintances and friends (naturally), because I can take advantage of the notes I keep on people’s interests and ask after those instead of talking about the weather. With people I don’t know, I try to take the lead in the conversation by asking questions. This means I can avoid the somewhat dead-end-ish “So, what do you do?” and use questions like “So, what are you passionate about?” or “What’s your story?” If I’m lucky, that gives me enough information for follow-up questions, and I can weave some self-disclosures into other questions or ideas to even out the conversation.

Managing my energy during events. A buzzing event can be overwhelming. A multi-day conference, even more so. I can tell when I’m getting tired and networked out: I start glazing over or feeling pressed in on.

I’ve learned to take my breaks unashamedly. Excusing myself is one way to do it. The women’s bathroom is often a quiet place to retreat to. Other times, I’ll go for a walk. In a pinch, I can hover on the periphery of a conversation that I don’t need to participate in, or take out my paper notebook and update my notes, or pretend to answer e-mail while clearing out my brain.

Following up afterwards. Okay, so I’ve met people and they’re potentially interesting, but then what? If I don’t bridge the gap between that and the next conversation, then it’s just conversation practice and the slim chance of being remembered in case we bump into each other again.

It helps to realize that most people suck at this too. You know those exchanges of business cards and contact information? I tend to follow up with more people than people follow up with me, and that goes for extroverts too.

I try to make it easier by giving myself homework during the conversation. If I think of a relevant book, for example, I might promise to send the details and a short description. If I’m at a conference, I might promise to send my notes. Then I have a built-in excuse for writing.

Building the connection from there. Because I rarely go to events or hang out in cafes, I tend to not bump into people much. However, it takes quite a few conversations to build a connection. Some people are comfortable inviting other people for follow-up lunches or coffees. I’m still getting the hang of that myself.

Blogging makes it easier for people to get to know me. I link to my blog in my e-mail signature, and try to share notes of events as another way to create value. If other people blog or post on Twitter, I subscribe to their updates too.

So that’s what I’ll work on helping other people with:

• Creating opportunities for serendipity
• Starting conversations
• Continuing the conversation past small talk
• Managing my energy during events
• Following up afterwards
• Building the connection from there

Can you think of other things that might be challenges for introverts too?