> How do you know what to say?, usually I can start the conversation but I don’t know where to take it after. Some ideas: Ask what they’re passionate about. Talk about what you’re passionate about. Say you’re trying to improve yourself and ask if there is anything they’ve learned lately about life that you should know. Ask for their advice/opinion on a recent problem you’ve faced or something that surprised you recently.

>How do you get over the feeling that you are wasting their time? First, hold up a mirror: do you feel your time is wasted when someone talks to you? Second, everyone benefits from bonds and talking enables trust. Even if the relationship is temporary, it brings comfort. Think of two people at an airport going out on different planes. Even a short conversation with someone makes them trust enough to let the other watch their heavy luggage while they go to the bathroom.

>Finally, how do you end the conversation when you're still going in the same direction or waiting at the same place? Yeah, this is always a little awkward. You can just say something like “It’s been nice talking to you. I’m going to go back to reading my book.” Sometimes I’ll make a polite fib like saying I’ve got to think about an important presentation or have some pressing emails that I need to read.