What are the best questions to help start a new relationship or conversation?

By Andrew Sobel

After a recent live interview that I did with my friend and bestselling author Dorie Clark, a listener wrote in and asked this question: As an introvert I would love to know from Andrew what are the top three opening questions that he recommends to start a relationship/conversation?

It would be poor advice to say “Here are the three best questions—in all situations—to start a relationship.” It very much depends on the circumstances. So first, let’s set the stage.


When you first meet someone, your questions have three overlapping goals. First, to break the ice and get the conversation going. Second, to find things you may have in common that are connection points. Studies show that rapport (and specifically, likability) is accentuated by the feeling that you share commonalities or similarities. And lastly, to learn more about the other person.

Personally, I’m very focused on number two—finding things we have in common. So when I’m preparing for a call or meeting, I spend much of my time learning about the person I’m going to meet with rather than devoting hours to reading annual reports. This background will give me important information to help me connect and focus the discussion.

Take it slow—especially if you are an introvert. Don’t ask overly personal questions right off the bat. Start with something light. It could be as simple as “Has spring arrived yet?”, referring to where they live, or “How has your week gone so far?”

Nowadays, where so much communication is by phone or video conference, I often start with “Where are you calling from today?” or “Where are you based?” The answer can quickly lead to a follow up question that relates to where the person lives—for example, “Are you from that area originally?” or, “How would you compare living in New York to Chicago?” if they recently moved from one city to another.

If I find something in common in my background research, or on the spot as we talk—e.g., we both worked for the same company, grew up in the same city, went to the same school, have a friend in common, are involved in similar nonprofit activities, have a similar family situation, are involved in the same sport, and so on—I might linger on that for a minute or two by asking a follow up question.

I then like to move quickly to more substantive questions. If I see that someone has only been at their current company for a short period of time, I’ll ask about that—“I understand you moved to Acme fairly recently…I’m curious, how has your first year gone?” or even, “How would you compare the two cultures?” A little later in the conversation I might go deeper, and ask something like, “What are you working on right now that you’re especially excited about?” That’s a more “personal” question that draws out emotions not just information, and it can really get the other person engaged. During the conversation, if someone describes an experience or event to me, I sometimes ask, “What did you learn from that?”

Of course, if you’re meeting someone at a conference and you know absolutely nothing about them, you’ll need to start with very basic questions such as “What sort of work do you do?” or “What’s your connection with this event?” Good ice-breaking questions get the conversation started. They encourage the other person to talk. They refer to current events or happenings. They are also not personally intrusive or inappropriate (e.g., “That’s a gorgeous dress–who is it by?” It goes without saying, don’t make comments about someone’s clothing or appearance unless you are at a Halloween costume party! Save those remarks for your best friend).

Above all, any questions you ask have to be motivated by a genuine and authentic curiosity about the person you’re talking to. If they sound robotic or overly-rehearsed, you’ll risk coming across as insincere. Don’t be tense—remember, people love talking about themselves. Relax and smile when you ask these rapport-building questions, and then enjoy the conversation!


My newest book, It Starts with Clients: Your 100-Day Plan to Build Lifelong Relationships and Revenue has just been released. The chapter entitled Week 10: Use Power Questions  gives you the essential tools you need to develop your own Power Questions.

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