The All-Too-Common Scenario
You're at a company networking event, holding a paper plate of appetizers. You introduce yourself to Maya, a manager from the Product Development team whom you haven't met.
“How’s the new widget project going?” you ask, trying to sound interested.
“Oh, it’s keeping us busy,” Maya replies. “We’re mostly just waiting on the final compliance reports from legal before we move to the next iteration.”
You nod. Compliance? Iteration? You feel your mind go blank. You’ve hit the conversational wall that happens when surface-level small talk runs out. You want to build a real connection, but you don't know how to bridge the gap between your world and hers.
The key to connecting isn't mastering complicated topics; it's mastering deep questions. Top communicators know how to steer a dialogue away from bland facts ("How are you?") and toward what people genuinely care about.
The Power of the Deep Question
Most shallow questions only ask for facts, like "Where do you work?" These often lead to conversational dead ends.
Successful conversationalists use questions that ask people to share their values, beliefs, judgments, or experiences. These types of inquiries invite connection. When you ask a deep question, you are helping the other person feel more connected and drawing yourself into a learning conversation.
When you transition from questions about facts to questions about feelings, you unlock the mindset necessary for true connection.
10 Questions to Build Real Connections
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"How do you spend most of your time?" This subtle rephrasing avoids the common, often judgmental question, "And what do you do?" It’s a gracious way to learn about their job while reinforcing that you are interested in who they are, not just their title.
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"What's the best part of your job (right now)?" This transforms a question about facts (their role) into one about values (what they enjoy). By focusing on "the best part," you encourage a positive demeanor.
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"Are you glad you chose this field/career path?" This invites the other person to reflect on their choices and feelings—a question that encourages a deeper conversation than simply describing their work.
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"What’s one thing you hope to accomplish this year that isn't on your official performance review?" This question pushes past corporate mandates and gives them a chance to share a personal goal or dream. It taps into their aspirations, which helps build trust.
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"What’s a major challenge you overcame recently that you felt proud of?" Asking about experiences where they overcame a challenge invites stories of growth and achievement. People love sharing their own accomplishments.
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"What do you enjoy doing outside of work that you never thought you'd try?" This is a gentle way to probe their interests and hobbies. By asking about unexpected hobbies, you might tap into areas where they are proud to have learned something new.
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"When you're dealing with a difficult situation, what kind of support do you usually need—advice or just an empathetic ear?" If a colleague is venting, this question is powerful. It clarifies the conversational goal and shows you are listening closely and want to meet their needs.
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"What was your favorite part about growing up here / attending that school?" If you know where they are from (or went to college), shift the focus from the generic fact to their experiences and preferences. This makes the reply more personal and engaging.
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"If you could pick one value that drives your work decisions, what would it be?" This is a direct inquiry into their core beliefs. Understanding someone’s internal logic is a key to connecting.
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"What makes you feel most grateful right now?" This invites the discussion of personal values and positive beliefs. Sharing personal information about experiences and beliefs causes people to feel more connected.
The Secret Ingredient: Follow-Up Questions
A deep question gets the conversation rolling, but the follow-up question keeps it alive.
Follow-up questions are powerful because they are a strong signal that you are genuinely listening and want to know more.
For instance:
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Them: "I'm most proud of how our team handled the last project deadline."
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You (Follow-up): "What specifically did your team do that made you feel proud of that effort?"
When you ask someone how they feel and then immediately follow up, you are building a moment of true connection.
By mastering these simple questions, you will appear as a confident and charismatic "big cat" in the professional world.
To discover the other "little tricks" that the most successful people use every day to perfect the art of communication, check out our book, Communication That Wins.