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Based on the most helpful WSO content, here are some pleasantly surprising questions that professionals have appreciated during coffee chats:

  1. Personal Career Choices:

    • "What led you to a career in investment banking?"
    • "Why did you choose to work for [specific firm]?"
    • "What has been your favorite experience or deal in investment banking so far?"
  2. Personal Interests:

    • Steering the conversation towards their hobbies or interests outside of work can be refreshing. For example:
      • "I noticed on LinkedIn that you're into [specific hobby]. How did you get into that?"
      • "What do you enjoy doing when you're not working?"
  3. Unique and Thoughtful Questions:

    • "What surprised you the most about transitioning from an intern to a full-time role?"
    • "What advice would you give to someone navigating the networking and interview process during college?"
  4. Human Connection:

    • Asking about their personal journey or challenges can make the conversation more engaging:
      • "What’s one thing you wish you knew before starting in IB?"
      • "What’s been the most rewarding part of your career so far?"
  5. Avoiding the Usual:

    • Professionals often appreciate when the conversation moves away from repetitive work-related topics. For instance:
      • "What’s a book, podcast, or show you’ve enjoyed recently?"
      • "What’s a memorable vacation or trip you’ve taken?"

Remember, the key is to show genuine interest, actively listen, and connect on a personal level. Avoid overly technical or aggressive questions, as they can come across as showy or off-putting.

Sources: Good questions to Ask in Coffee Chats for Investment Banking, What Do You Even Do During Coffee Chats????

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