There was an obvious “creep factor” in Amy’s first attempt at speed dating. But that didn’t deter her from, as she puts it, “honoring the genuine goodness” of the rest of the group. Amy’s like that. She’s earnest in giving other’s sincere praise (even when they may not deserve it.)

Her girlfriends, on the other hand, weren’t so generous. They worried about being rejected. Even worse, being rejected by a guy that was below their standards. And what should they say in those quick five minutes? How would they make a good impression? It turns out their anxiety led to inert conversations with both sides talking about themselves.

Their approach isn’t uncommon.

Researchers from Harvard listened to conversations in places like bars and trains and found that two-thirds of the time people spoke about their personal experiences. It’s as if they were stuck in a never-ending job interview trying to sell themselves. I’d say that my only flaw is that I work too hard. That kind of self-promotion is not only exhausting, but it also keeps our relationships in shallow infancy.

Amy was determined to make her experience different. And while most of the men opposite her received candid praise; only a small fraction made the “datable” list. The difference? They asked questions. “I’ve learned some men don’t know how to ask about others,” she says, “it’s rare for a guy to do that well.” But when they did? “It felt inviting.” 

Amy’s datable list consisted of Conversational Designers—the kind of people that have mastered the art of elevating others by sincere inquiry. When psychologists followed speed daters like Amy they found out that “people who ask a higher proportion of follow-up questions have increased date success.” That means more second dates—regardless of their cologne count or comb-overs! Further, “people who tend to draw out more information from their conversational partners are better liked”. So cancel your Tinder account and say good-bye to your parent’s basement fellas!  

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The How Are You Habit

Stop me if you’ve heard this one. An acquaintance saddles up behind you in the checkout line. It’s been a while so the moment has come to re-socialize. (An eye-rolling moment for any self-respecting introvert to be sure). But regardless of your social disposition, all of us have adopted a hackneyed routine. And it’s time to stop. 

…we have to get real about our insincerity and authentically engage in other people’s lives. 

“Hello Jana”, you say with an affected smile. “How are you?”

“I’m good.” She responds, “How are you?” 

Did you catch it? Three little words that have set the tone for the rest of the conversation. How are you? It’s a question she didn’t really mean. And an answer you don’t honestly give. We could have blood oozing from our eyeballs by the latest pandemic cocktail and we’d still respond the same.

This greeting has become a perfunctory introduction and if there’s ever been a need to invigorate our real-world relationships, it’s now. Thankfully, there is a better way. But we have to get real about our consistent insincerity and authentically engage in other people’s lives. 

This means expunging the how-are-you-habit and replacing it with something called Observant Inquiry. As the name suggests this approach requires you to take a stand and flat out ignore the questions “How are ya?” or “How’s it going?” Don’t worry, it’s not rude. In fact, the line is so common they don’t even realize they asked it. Instead, you respond by affirming the individual with a positive observation and then follow up with a genuine question. It’s conversational elegance:

• “Hey, Anita how’s it going?”
• [Observation: Steve you’re here early again!] 
• [Inquiry: How do you manage your time so effectively?]

• “How are you Max?”
• [Observation: Jana the last time we spoke you mentioned a new design project.]
• [Inquiry: How is that going?]

• “Hey, Jared what’s up?”
• [Observation: Yin, your ideas at lunch were insanely creative.] 
• [Inquiry: Tell me more about your creative process?]

• “How’s it going?”
• [Observation: Mom, you were so kind to send your last text.] 
• [Inquiry: How do you keep others in mind when life gets so hectic?]

Question-based kickstarters like these esteem others and—if that’s not reason enough—make you far more likable. That’s not only important for those who rely on dating the old-fashioned way like Amy, but for each of us in our daily interactions. The trick, according to Amy, is “going in with your eyes wide open.” Because Observant Inquiry requires a little forethought—especially in daily circumstances like the gym, office, or coffee breaks. But let’s be honest wouldn’t our world would be a far better place if we spent just a few seconds considering the positive qualities of our co-workers? 

Here are a few ways to ensure your Observant Inquiry is sincere:

1. Before your next important meeting write the name of one person. Consider what makes them special and what you can learn from them.
2. When doing your daily planning identify a single Observant Inquiry for someone you know you’ll see that day. Write it down.
3. When you catch yourself criticizing someone ask yourself if it’s really true? What is one quality can you honestly affirm.

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The Question doesn’t have to be perfect

Dr. David Cooperrider had has spent a lifetime helping individuals and companies craft questions in a positive way. As he explains it, most often people are obsessed with the exact phrasing of a question. When the reality is the mere presence of sincere inquiry creates the fertile dialogue that sow the seeds of change. “It is not so much is my question leading to a right or wrong answer,” says Cooperrider, “but what effect is my question having on our lives together.” Questions foster a special bond by creating a joint learning experience.

Observant Inquiry validates others quickly and acknowledges their distinctive individuality. And according to multiple meta-studies, it’s a healthy bet they need this validation. All of us, after all, are in some way wounded. Making each encounter a peak experience may lead us to what Amy learned while speed dating. “It’s amazing how quickly you can connect with people.”