From Small Talk to Big Impact
The Art of Asking Engaging Questions

Mastering the art of asking engaging questions is critical when networking. Shifting your focus from self-promotion to genuinely understanding the other person’s interests, challenges, and goals unlocks the potential for meaningful conversations and building deeper connections.

Asking the right questions is a powerful technique to initiate a conversation and gain valuable insights into the person. It’s time to move beyond generic questions like “How are you?” or “What do you do?” Instead, create thought-provoking questions to prompt people to share unique experiences (think restaurants and travel), aspirations, and perspectives. This approach allows you to uncover shared interests and establish a quick rapport to build mutually beneficial relationships.

Here are three tips to help you ask more engaging questions:

Show Genuine Interest:

When asking a question, ensure it comes from genuine curiosity. Inauthenticity will ruin any potential for building a meaningful connection. By demonstrating a sincere interest in the other person’s experiences, you increase your chances of establishing a positive connection.

Favorite question: What’s new and exciting in your world?

Listen Actively:

Once you’ve asked a question, practice active listening by absorbing their response. Avoid interrupting with your own thoughts or experiences. Instead, show engagement through non-verbal cues like making good eye contact, nodding your head, and ask insightful follow-up questions. Active listening enables you to gain a deeper understanding of the other person’s needs, aspirations, and challenges.

Key: Train your mind to listen with your eyes.

Focus on the Other Person:

Networking success hinges on shifting the focus from self-interest to the needs of others. By centering your questions around their specific interests, challenges, and goals, you lay the groundwork for cultivating lasting relationships. The key is in being genuinely interested in the other person rather than trying to sound interesting.

Favorite question: Who are you looking to meet at this event?

The art of asking engaging questions is an essential skill to create successful relationships and lasting connections. It’s a skill you can plan and prepare for, and like everything else we do, practice makes perfect. By genuinely showing interest, actively listening, prioritizing the needs of others, you will unlock valuable insights, establish deeper connections, and achieve greater success in your professional and personal life.

So tell me, what’s your favorite question to ask a new connection?

Derek Dickow specializes in turning people who think they hate networking into Power Connectors. He hosts networking events, leads 1:1 executive training, and offers corporate bootcamps designed to help organizations maximize success through networking. Derek knows that confident networking is a skill anyone can learn — and everyone needs. Download Derek’s free Networking Guide here.


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