TIP ONE: ASK DEEP QUESTIONS
A deep question asks someone about their values, beliefs or experiences. Rather than asking someone about the facts of their life (“Where do you live?”) it asks how they feel about their life. (“What’s the best part of where you live?”) Studies show that people love answering deep questions, because it gives us a chance to share something meaningful about ourselves.

“Like when I’m on a train, talking with people commuting to work, I might ask them, ‘What do you do for a living?’ And then I might say, ‘Do you love that job?’ or ‘Do you have something else you dream of doing?’

We only really feel connected to someone if we believe they are listening – and so it’s essential that we prove we’re listening. One easy way is follow-up questions: They show we’re paying attention (and will help the other person to like and trust you.) Another technique, particularly for tough conversations, is looping for understanding: Ask a question (preferably a deep question). Repeat back, in your own words, what you heard. Then – and this is the step most people forget – ask if you got it right.  

But when someone exposes authenticity, and we don’t respond in kind, a conversation can feel one-sided. People might feel unappreciated or judged.

So it’s important that we engage in ‘reciprocal authenticity’: When someone says something real (“I went to my son’s graduation this weekend, and it was amazing”) reply with something similarly authentic (“Oh, wow. I can’t wait for my kids to reach that stage – but, I’m also a little sad they’re growing up.”) Meaningful connections come from sharing authentic parts of ourselves.