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Start With a Question - Candid Kam

Start With a Question

Many of you know my husband Sunny, but what you may not know is that he is the King of Questions. He loves to inspire conversation with a question, whether at a dinner table or over coffee at a conference. Getting others to discuss their learnings is a great way to break the ice and develop a deeper connection with individuals. Sometimes, these conversations can even lead to learning more about those around you, including your own children. 

We celebrated our son, Sahib’s 22nd birthday on Wednesday and went out to dinner at Gabriella’s Steakhouse in Red Bank. First, the food was amazing—definitely get the garlic bread if you ever visit. As we all settled in to wait for our appetizers, Sunny began with his question for our kids: 

  1. What is the greatest lesson you have learned this past year? 
  2. What was the most monumental moment of the year? 

Since we have conversations often, we wanted to limit the timeframe of the question. As we went around the table, we landed on our middle son, Rohan, who began university this past year. He is not usually the talkative one—seriously, have you met Shaan?—but he is extremely thoughtful. When it came time for his turn, he spoke about the relationships he had built this past year in school. He had made many new friends and felt that there were so many different characteristics he admired in each one. 

His learning was that each person in his life had qualities he admired, and he was conscious of spending his time with those who added value to his life. 

WOW—now as a mom, I got teary-eyed, and I know Sunny was extremely proud in that moment. We learned then the depth of his thoughts and how our 19-year-old was developing into such a sensible young man. Sometimes broody but always kind and thoughtful, he had learned an extremely important lesson already in life—to choose the people around you wisely and to ensure that those in your circle add value to you. 

A simple question can help you learn so much about someone, even if that’s your own child. It was interesting to hear that the boys mentioned how much their friends enjoyed it when Sunny asked them questions and sparked deeper conversations with the kids. There is a sense of intentionality in the conversation, and it makes people really think about what their life means to them. 

Now, I know what you’re waiting for—what about the other question? Rohan’s most monumental moment of the year was making these new friends in Boston. He felt it made the most impact on his life and provided the greatest lesson. His high school friends were nice, but here, he was wiser with his choices and built a community of like-minded individuals who added value to one another. 

Like I said, I’m really proud mom here. So, what can we all learn from this? The next time you go to dinner, whether it’s with friends you’ve known a lifetime or a new acquaintance, think about starting the conversation with a question. Some of our favorites include: 

  1. What is the greatest life lesson you have learned? 
  2. Who do you know that I should know? 
  3. If you could go back and change one thing in your life, what would it be and why? 
  4. If you could instantly become an expert in any field or skill, what would it be and why? 
  5. If you could have dinner with any person, living or dead, who would they be and what would you want to discuss with them? 
  6. What’s a piece of advice or life lesson you’ve received that has stuck with you over the years? 

Please share any of your favorites in the comments on this article; we’d love to add to our list. You will be surprised at how much you will learn about people, even those closest to you, that you had no idea about. We don’t usually go this deep, and sometimes that’s what is missing for deeper connections and bonds. Take the time, start with questions, and be a curious listener—you’ll be surprised at all that you can learn. 

For more content like this, be sure to follow IT By Design on LinkedIn and YouTube, check out our on-demand learning platform, Build IT University, and be sure to register for Build IT LIVE, our 3-day education focused conference, August 4-6, 2025 in Jersey City, NJ!

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