Some of my clients feel they’re bad at conversation. This composite essentializes it:
First of all, I’m shy to go up to people. And even if they come up to me or we’re already meeting, I don’t know what to say after “hello.” I’m always afraid I have nothing to say that isn’t boring. And then there’s that deadly silence—so awkward. So I tend to avoid talking to anyone I don’t already feel comfortable with. I know that hurts me professionally and personally but I don’t know how to improve.
My clients have found these steps helpful:
1. Prepare a bit. What could you talk and ask about: family, work, current events, a hobby? Starting with small talk is just fine: It’s what helps people settle down.
2. Start with an environmental comment. I’m not talking about climate change but about the immediate environment: the room, the weather, the common reason the two of you are there. For example, “Hi, this is my first time at this meetup (or restaurant, conference, whatever.) You?
3, Ask an easy question, ideally one that finds common ground, as in the previous example. Another example: Let’s say you’re in your workplace’s breakroom, TGIF, or party. You might say, “I’m working on the Version 2.0 rollout. How about you?"
4. Listen carefully. Especially if you’re insecure in conversation, it’s tempting to think ahead to what you’re going to say next. But it’s important to listen well, curiously, and then ask a follow-up question or add something to what the person said, again perhaps finding common ground. For example, “It seemed that your tone got a little darker when you said you had a sister. Maybe I’m projecting because I’m having a hard time with my brother.” Then wait, give the person time to think.
5. Accept discomfort. At some point, you won’t know what to say or feel you said something mundane if not downright stupid. Your conversation needn’t score 100%. In fact, you could score a big, fat goose egg and you’ll survive. But if you can muster the grace to laugh at yourself or at least be quiet and allow the other person to fill in, all will be good or at least good enough.
6. When things get sticky. For example, you’ve put your foot in your mouth, the other person annoyed you, or you have no idea how to respond. It’s beyond this post's scope to address specifics but the generalizable point is: Cut your losses. For example, give a brief answer to a hard question. That’s the opposite of the natural tendency to talk and talk in hopes you'll dig your way out. Then divert attention by asking a question. If you’ve screwed up, it's often wise to laugh and say something brief like “I misspoke” and move on to something safe or ask a question. If you’re unhappy with something the person said, breathe to give yourself a moment so you don’t act reflexively. Then ask yourself, "Is it wise to confront or deflect?"
A conversation’s open-endedness can be scary: Where do you start? How do you continue? What if you get stuck? What if things get awkward? A conversation can be a bit like walking a tightrope. Fortunately, if you fall, you’ll get up, guaranteed. And if you follow at least some of this post’s tips, chances are you’ll not only get to the other side but have enjoyed the walk.