The 9 Cut Through Questions
The Art of Open Ended Questions.
We all know those conversations where you walk away feeling like you really connected with someone. I love those. They are moments when you go beyond the surface and get a glimpse into who someone truly is—their story, dreams, and struggles that shaped them into the person they are today and give you an inside look at where they are going. But I’ve realized that connection doesn’t just happen by chance. It happens when you ask the right questions.
This list of questions almost always leads to deeper conversations. These nine questions have been game-changers, whether with a close friend or a new acquaintance. Let me share them with you.
1. What’s your story?
Allowing someone to share their childhood, career, or pivotal moments. It gives them space to define themselves from experience.
2. If your next five years were a chapter in a book, what would the chapter be about?
This question sparks creative thinking about the future. Are they pursuing a dream, creating something new, or enjoying the moment? Their answer reveals their passions, goals, and vision for the next phase of life.
3. What would you do if you weren’t afraid?
This question reveals a desire they’ve held back due to fear. It’s powerful, tapping into hidden wants they may not admit to themselves.
4. What has gone really well in your life so far?
Sometimes, people get so caught up in what’s wrong that they forget to celebrate what’s right. This question is like a little flashlight—it helps people shine a light on their wins, big or small.
5. What’s a lesson you learned the hard way?
This is one of the best questions to bring someone down to earth. People often share stories of failure, heartbreak, or tough decisions, but there’s always a silver lining. In those stories, I see their resilience and growth.
6. What’s the best thing about being you?
This question is unexpected and can catch people by surprise. However, I appreciate it because it encourages them to reflect on their uniqueness. Their responses are straightforward yet meaningful—such as their kindness, curiosity, or sense of humour.
7. What’s something you wish other people knew about you?
This question is fascinating because it allows people to share something they might feel misunderstood. It could be a hidden talent, a part of their personality, or a struggle they don’t discuss often. It’s a window into the part they don’t usually share.
8. What’s your favourite thing to do in the world?
Everyone lights up when they talk about their favourite thing. Whether it’s a hobby, a place, or just spending time with loved ones, their answer reveals what brings them the most joy. And who doesn’t love hearing someone talk about what makes them happy?
9. What’s one mistake you learned the most from?
This question often leads to some of the most honest answers. Mistakes are part of being human, and how someone talks about them tells me a lot about their character. It’s not just about the mistake—it’s about what they took away from it.
Let me know what questions you have the most success unwrapping the complex humans we encounter.
Cheers,
NB.