How To Talk To Anyone – 10 Foolproof Questions for Great Conversations

  • Published on:
    June 20, 2022
  • Reading time by:
    5 minutes
How To Talk To Anyone - 10 Foolproof Questions for Great Conversations womenontopp.com women on topp

No matter what role you hold in life personally or professionally you will inevitably find yourself in a situation talking to a stranger. Sometimes you click immediately and hold lengthy conversations with ease; other times, you feel so awkward that you’re searching for any reason to exit.

We tend to prefer what we know and stick to what’s comfortable, so it can be difficult to venture into conversations with unfamiliar people. Our brains decide in the first seven seconds of meeting someone whether we like them or not. We are hardwired to judge whether someone is more like or unlike us; the more “unlike” we determine them to be, the more we want to withdraw from being around them.

As a result, we have to make a conscious decision to override our unconscious brains. And the good news is that we can do this simply by telling ourselves (usually internally, not out loud!) to stay “open and curious”.

If you are willing to remain open and curious during a difficult conversation, then you’ll discover more ease and enjoyment with even the most awkward people.

When we let curiosity, rather than judgment, drive our conversations, we uncover information that was previously hidden. We travel a conversational path that is surprising and that allows us to connect with the other person in unexpected ways. Openness and curiosity become a playing field on which the words of our conversation have a friendly engagement. Conversations become less work and more fun.

To stay open and curious, we have to withhold judgment. We have to choose to listen to the other person with the goal of connecting to her, and we connect by asking great questions that we care about knowing the answers to.

Are you ready to try? Here are 10 questions that I keep in my back pocket (of my mind) when I’m meeting someone new. I encourage you to test out a few that seem interesting during your next work party or networking event – or even at home around the dinner table with family or friends.

Remember – the question is just the starting point. It’s up to you to keep the conversation going by letting your curiosity drive it!

10 Foolproof Questions for Great Conversations

1. What’s the most encouraging thing that’s happened to you this week?

This is my #1 question because it gets the other person thinking about a positive event in her life. I don’t think we share enough of our wins with one another because we fear sounding like a braggert, so this question invites the other person to safely celebrate herself because you want to celebrate with her.

2. What goal are you working toward right now?

As a coach, I’m always interested in knowing where people are headed. This question opens up the imagination and dream centers of our brains, and it gives me an opportunity to encourage the other person to keep going (and we all need a little encouragement!).

3. What’s the best advice you’ve received?

People like to feel useful and contribute value, whether to an organization or within a relationship. This question is a small way that you can ask a new contact to share some of her favorite wisdom with you.

4. What problem are you trying to solve (in life or business)?

I’m a natural problem-solver so I love asking this question to see how other people are processing their own obstacles and determine if I can help in some way. Be careful, though! Most people don’t want unsolicited advice. If someone is open to sharing her current dilemma with you, consider how you can best support her rather than rush to solve the problem. 

5. What’s inspiring you right now?

We all need a little inspiration in our lives, so why not get some from the people around us? I never fail to learn something new when I ask this question because the answer gives me insight into the person herself (what types of things inspire this person?) and also because her response may lead me into a new direction for myself.

6. What are you reading (or listening to)?

This is an easy question to start a conversation, but I suggest using it only if you have a response of your own because it’s also the most likely question the person will ask in return. 

7. What are you really good at?

This question is best asked once you have already started a conversation and discovered some background information about the person’s interests, hobbies, and job. It’s another invitation for her to share something she’s proud of without fear of sounding arrogant. 

8. What’s the most surprising thing that’s happened to you recently?

When we’re struggling to keep a conversation going with someone we don’t know well or don’t feel connected to, this question can open up a whole new range of topics. The answers can be humorous, uplifting, or even reveal a discouragement that the person recently faced. Tossing this question into the conversational mix gives you a chance to really enter into the other person’s world by tapping into empathy.

9. What are you feeling most excited about right now?

We give people a great gift when we enter into their joys, and this question can boost both your moods.

10. Why?

No matter what question you lead with, the best way to keep the conversation going is to follow up with “why?”. Asking why not only keeps you open and curious, it also leads the conversation well beyond surface level. When we ask “what inspires you?” and then investigate why that particular answer is inspiring, we engage the more compassionate parts of our hearts and form deeper connections with other people.

Remember, all humans have a deep need to be seen, heard, and understood. When we enter conversations truly open and curious about the person in front of us, and when we ask questions that matter, then we both get the pleasure of connecting. And who knows? You just might make a new friend.

Nicole Devereaux

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