How To Connect With Anyone You Just Met With 5 Questions

All my life, I’ve began asking myself, “Whom can I connect?” I am naturally hard-wired to see the world as a web of relationships and I get excited by the prospect of connecting people within my web. Not because they will like each other, but rather because of what they will create together. The mantra I operate in is “1 + 1 makes 3. Or 30. Or 300. ”

Entering a new career transition as an entrepreneur and leadership coach/consultant, I am constantly finding ways to build connections and find ways on how I can be for them and against them.

I came across five types of questions that have helped me to improve my emotional connectivity with people. I hope you’ll find the following helpful in building your relational intelligence.

1. Establish Common Ground

Are you able to quickly identify things in which you have in common? Whether that is, your blood type, month you were born, ethnic background, alma mater, organization you work for, hobbies, mutual friends, my number one objective is to start a conversation based something we share in common. This ignites our conversation and helps to take it to the next level. Finding common ground is the lubricator of the relationship engine.

Simply, start looking around. What do you notice in the other person in which you can ask questions to create resonance and commonality? Here’s some examples.

  • “Those are nice looking glasses. Looks exactly like the design I’m looking for. Where can I purchase them?”
  • “It really sucks to wearing a tie when it’s sweltering, isn’t it?”
  • “Isn’t the iPhone 6 so convenient for situations like this?”

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2. Ask Questions the Other Person Wants to Hear

This is second nature to master connectors. They are Jedi-masters when it comes to listening between the lines. They intuitively know what the other person wants to be asked.

Here’s a normal response from an average questioner:

  • Person A: “How did you spend your long-weekend holiday?”
  • Person B: “I visited Hawaii with my family on Friday and had a fantastic time there.”

Now, here’s a normal response from an exceptional questioner:

  • Person A: “How did you spend your long-weekend holiday?”
  • Person B: “I had a three day off-site visit with family. What about you?” 

Did you catch the difference? In the second scenario, Person B intuitively knew that Person A brought up the question because Person A wants to share his/her experience. That’s why Person B gave a general reply and quickly turned around with the same question to Person A. If you really think about it, a lot of the questions people asked are questions they want to be asked.

Here’s more examples:

  • “Honey, did you hear? Our neighbor Jim’s went to Hawaii again.”
  • “Were you involved in student clubs while you were in college?”
  • “What are the best books you are reading?”

In the first question, the person’t isn’t confirming whether you know that Jim went to Hawaii. The question implies a desire, “I want to go to Hawaii too.” In the second question, “the person isn’t really asking for which clubs you’re involved in college, but rather this person wants to share about his/her student club experience during college.” Same logic for the third question. The person is more interested in sharing his thoughts on the best books he is reading. Exceptional connectors intuitively know this because they are always others-focused.


3. When You Ask, Use “Half Open-ended Questions”

Generally, there’s two type of questions. A closed-ended question and an open-ended question. Here’s an example of these two type of questions:

  • Closed-ended Question: “Is working at your job hard?” (Either you respond with “yes” or “no”)
  • Open-ended Question: “How is working at your job?” (The person can freely respond)

We ask these questions all the time. When we meet people for the first time and ask closed-ended questions, the conversation may abruptly halt and create awkward moments. When you use open-ended questions, the question is so big and abstract that the person responding may have difficulty sharing “how much” information.

Instead, employ the “half open-ended question” method. This is when you create more specificity into the open-ended question method. Here’s a few example:

  • “What’s your favorite thing about working in your current job?”
  • “What’s the hardest thing from taking this class?”
  • “What makes this season the busiest time in life?”

A small thing like adding a bit more specificity can make all the difference.

4.Use Questions to Elicit Interesting Episodes

Master connectors learn from one of the most commonly used interview strategies today: behavioral interviews. Instead of asking “general questions” such as ”

  • “What’s your strength?”
  • “What’s your dream job?”
  • “What’s the most important thing you have learned from your role as a customer service rep?”

A lot of times, these questions are often responded with quite abstract terms. Rather, behavioral interviews focused on specific, concrete examples of the past that demonstrate certain qualities. Here’s a few examples:

  • “Can you tell me about an experience in your current role where your strength came to limelight?”
  • “What’s your current role at work? Tell me a success story of one of your accomplishments this year.”

One caveat is ensuring that you focus on both tact and tone. These questions can often sound intimidating. So, it’s important to sound genuine and interested, not like an interrogator. When you use this method here’s a few examples of what it might sound like in a conversation:

  • “Oh. I see. Interesting. So what specifically happened after that?”
  • “So what happened to that guy after it happened?”

5. Leverage the Power of Research

We live in a world where transparency is the currency of relationship and information is free on the internet. Whether it’s a blog, Facebook, Twitter, or Instagram, this creates an opportunity for master connectors to do pre-work to ask the right questions when you meet the person for the first time.

Whether you are preparing for an interview, going out on a date, or preparing for a networking session, I always spend 30 minutes to an hour to really research the person. I immediately think about what do I share in common? Also, I might follow the person beforehand and read their tweets to see what kind of information this person is interested in.

My Favorite Books on Building Social Intelligence:

Question: Which areas do you plan to focus on to upgrade your connection skills?

  • I love this Paul because sometimes I’m really bad at this and I don’t know what to say or what questions to ask, however, I know it’s important because it’s those starter questions that lead to the bigger questions and the deeper relationships! I like the idea of the half-opened question, I’ve never thought about questions like that before. I’m going to try them out.

    • Definitely. Let me know how it works brother.

  • This is a great list. I find it really difficult connecting with people I first met; I can come off looking cold. I’m going to give some of these suggestions a try!

  • Sharing this with my team at church! 🙂

    • Thanks Lorna! Hope they find it helpful!

  • Alex Tran

    Great read. Definitely going to try this out. I want to transform my conversational skills – no more awkward conversations in the elevator!

  • elles

    great article

  • You have nailed it. I have been wanting to find something that just “said it” about connections. Each of us needs to “walk across the room” (Hybels) by faith and start the conversation. These 5 points give us some material to get those conversations going.

  • Hazel Dahl Behrens

    I’m a pastor in three small rural churches. I’m going to focus on asking questions to elicit interesting episodes in hopes to learn more about history of their church and their relationship with church.

  • Bill Rothchild

    Nothing new here if you’ve been working at improving your conversational skills over a long period of time.

  • Sue Kinrade

    Bill, I am with you on that, these things cannot be learned by rote, but by experience and actual usage. Debating societies and old fashioned after school clubs were the start of understanding the art of communication. If you were to take the type of syntax right off these pages and not be able to couch them in day to day usage you stand a chance of seeming like a stalker in training!

  • Akin

    I try often to relational, maybe there are bits of these I need to apply to become more powerful and all. It still comes down to one thing listening and personally listening more is something I need to deal with and be used to. Thanks for this Paul.


    Great tips! I am a recruiter and am used to asking questions all day. But, when it comes to marketing my brand, I tend to loose sight of the “art of asking” to gather the right information. Thanks again!

  • Excellent advice as always. Typically things go best when we are others-focused rather than focused on our own ambitions. I personally strive to find a shared value because that usually allows for a deeper connection and typically try to avoid surface level questions because what we talk about will inevitably shape the other person’s perception of who we are. Don’t just say something to make conversation, what we say says something about who we are.

  • kentvincent

    All good approaches, although I’d be a little wary of framing too many of these discussion questions like job interview questions along the lines of “tell me about a time when…” You’ve just unwittingly aligned yourself with all the “behavioral” interviewers that your guest would like to paddle with a wet noodle. i do like the follow on questions along the lines of “what did that guy/you do”? Everyone likes to hear an empathetic reaction to things we or those closest to us had to deal with in extreme circumstances, and the follow on dialog can bond us even further.

  • Andrew Linderer

    I’ve been working on all of these, though I didn’t have this framework to work from. Thanks for puting this together Paul. The interesting episodes are the hardest for me because, like a couple people in the comments have mentioned it’s tough not to sound like an interviewer. Your tone is the key to making this type of question work. Timing is also important. It’s better to start with a half opened or an area of common ground. Maybe a couple of those before you dive deep with an interesting episode. Great article Paul.

  • Lynn Hare

    These are great ideas. The other kinds of questions I add are follow-up questions based on their reply to these initial questions. Follow them down the path where the conversation naturally goes. Use reflective listening skills in the form of further questions of genuine interest.

  • IMFellowship

    Basically, you are encouraging us to move out of the all-to-common self-centeredness. How many people I have met and began asking them questions, and when parting after a half hour or more realize they know nothing about me? It’s so good to grow in expressing our interest in others! Thank you, Paul.

  • GrimmEngineer

    Or you could just be yourself, instead of the false “date-mode” a lot of people go into…