Ten Questions to Help You Start a Conversation

“In conversation, humor is worth more than wit and easiness more than knowledge” -George Herbert

How to Start a Conversation

Have you ever been introduced to someone but did not know how to start the conversation? Ever experience that awkward moment of silence not knowing what to say or worse, waiting for the other person to say something interesting?

No worries. Most of us have felt this way, especially at conferences and large conventions. Here are a couple of tips I’ve picked up over the years that you may find helpful.

First, keep in mind that a conversation is like a journey with the speakers going from one place to another. As with every journey, you must first learn how to take the first step and also figure out which direction you’ll be traveling.

An approach that’s worked well for me is similar to an approach I use when picking a jury during trial. Remember, I’m talking to 12 people I’ve never met before, and it’s my job to get everyone to talk about themselves so that I can learn more who my ultimate decision makers are. I need to know what they’re thinking and what makes them tick. To do anything less would be a disservice to my client.

I use the open-ended questions below to get the dance going. By the way, don’t try and use all these questions with the same person and at the same time. Instead, think of these questions as though they are ten arrows in your relationship quiver.

Learn these questions, and you can easily reach back in your mind and pull out the one question that’s perfect for your next ice-breaking opportunity. Remember, different questions apply to different situations so be careful with how and when you use them.

Hint- to develop rapport with the other person, it takes a bit more than just asking these questions. For example, after you ask your question, pay attention and be genuinely interested in the other person’s answer. Listen 70% of the time, make eye contact and smile.

Also make sure to use these questions in a natural and conversational fashion. Let the discussion flow and follow up the other person’s answers with new related questions. Nobody likes to be interrogated so let your human side shine through during the conversation.

So let’s get started. You’ve just be introduced to someone or, you’ve just walked into a room and are approached by a complete stranger.

1. What do you do for a living? How did you get started?

People enjoy talking about themselves so give them a chance to do just that. Let them share their story with you. Listen and learn more about the other person.

2. What do you enjoy most about your business or profession?

I like always to be specific when I ask this question. If the person I’m talking to is an author, I’ll ask something like, “What do you enjoy most about being an author?” or maybe, “What did you enjoy most about writing your new book, “Overnight Success?” as opposed to, “What do you like about your occupation?” See the difference?

Again, it’s a question that elicits a good, positive feeling. It will also get the conversation moving forward.

3. What separates you and your company from the competition?

This is a permission-to-brag question, and the answer will help you learn what the other person believes is special about her business. Again, be as specific as you can with “company” and “competition”. Sometimes this question may include not a company but an activity or charitable cause. Either way, this approach works very well.

4. What advice would you give someone just starting in the ABC business?

This is a mentor type of question. We all like to be perceived as experts in our field so let the other person shine a bit and possibly share some pearls of wisdom with you. [tip- when he or she answers this question, ask a follow-up open-ended question. For example, “That’s interesting, why is that so important?”]

5. What one thing would you do with your business (or life, interest) if you knew you could not fail?

This is a great way to find out what the other person’s true interest is. What are her dreams and goals?

6. What significant changes have you seen take place in your business or profession throughout the years?

This is a great question for someone a few years older than you. They’ve put in their time and usually enjoy sharing their opinions and stories.

7. What do you see as the coming trends in your business or profession?

This question asks the other person to speculate on the future. Think about this. Isn’t this a question that’s normally reserved for important guests on television shows like CNN? If the person happens to be an expert, you just might learn something from the answer. In any case, you’ll probably make them feel good about themselves just by asking the question.

8. Describe the strangest or funniest incident you’ve experienced in your business or profession?

People love sharing war stories so here’s their chance. Most people don’t get the chance to share these stories, and now you’ve volunteered to be their audience.

9. What ways have you found to be the most effective way to help others or to promote your business or profession (or issue you’re discussing)?

You’ll not only get good ideas to help you move forward with a project or business need, but you’ll also find out how this person thinks.

10. What one sentence would you like people to use in describing the way you do business or practice your profession?

You’ve just asked a question that most people are never asked. The other person’s answer will reveal quite a bit. They’ll also appreciate the fact that you care.

Conclusion

Use one or two of these ten questions to get your next conversation going in the right direction. Care about who you’re talking with and what they’re saying.

Be sincere and genuine. Make eye contact and stop looking down at your smartphone.

Finally and most importantly, enjoy the new relationship you just started!

Author: Mitch Jackson

I'm a California trial lawyer trying to fix the world one client, cause, and digital interaction at a time.

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