Entrepreneurs

10 Conversation Starters For Entrepreneurs Seeking Deeper Connection

There’s never a reason to run out of conversation topics. The news, the weather and whatever other people are doing could be talked about at length, in most scenarios. Those topics, however, are dull. No one learned anything meaningful about anyone else by making small talk. For entrepreneurs seeking deeper connection with people they meet, the magic lies in asking deep questions and then exploring the answers without judgement.

Roel Vogels is founder of Scenario Cards, an ecommerce brand that provides powerful “What if?” questions, developed by psychologists, that help their customers let go of their worries and insecurities. Inspired by his own journey with burnout, Vogels’ mission is to help people explore deeper conversations and start living their true purpose without the need for a life coach. The conversation starters are used in 70 countries, by customers creating mini coaching sessions within friendship groups.

The Find Purpose box of Scenario Cards includes versions of these ten meaningful conversation starters, to help you establish a deeper connection and get closer to your purpose.

1. If you could learn the answer to any one question, what would you ask?

What would you want to know if the power of knowledge was in your hands? Life’s great mysteries: explained. “You could follow up and ask why the answer to that question is important for you to know,” said Vogels. “It’s likely that your answer will reveal something you truly care about or show an area within your personal development where you’d like to accelerate your growth.”

2. If you died tomorrow, what would be your biggest regret about what you didn’t do in life?

When faced with the prospect of dying tomorrow, suddenly everything gets perspective. “We often postpone or ignore our core deepest desires for the sake of success or a career.” Vogels said that, “having a limited time left to live helps us reprioritise what it’s really all about.” Exploring this question within a group might uncover what really matters.

3. Upon release from a ten-year prison sentence, how do you spend your first day free?

The answer to this question is a true reflection of how you want to spend your time. Follow up questions, said Vogels, include, “When released, where would you run to? What would invigorate and revivify you? How do you know it would?” They remind you that you can choose how you live.

4. If you could change anything about your childhood, what would you change?

Since you were young there have been new inventions and new technology. But it’s deeper than that. “Your childhood shaped your personality,” said Vogels. “Answering this question will help you acknowledge why you are who you are today as well as what parts of your childhood you’re ready to let go of.” Make peace and moving on.

5. What would you write in a message to your future self?

Who do you want to be a year from now? Vogels says that this practice “will help you understand your core principles and beliefs.” The answer may reveal the advice you most need to hear. Once you know the advice, you know what you need to change. Asking this of friends can provide the accountability to become who they want to be.

6. If you lost your ability to communicate tomorrow, what would you share today that you haven’t told someone yet?

“Sometimes we hold back our truest words because of fears, projections and insecurities,” said Vogels. “This question will help you realise the burdens you need to relieve or the love you need to express.” Who needs to know what? Work it out, say what you need to say, and be free.

7. If you had all the money you could ever need, how would you live differently?

Asked in a group, this question is fun. One person describes their dream life and another incorporates some elements. The money is endless, after all. Vogels wants you to “remove your excuse of not having enough money to live your true purpose.” Instead, define your dream reality and take steps towards living it.

8. If you could change one thing about the world, what would you change?

“Answering this question will reveal a cause you deeply care about,” said Vogels. Perhaps it’s one you hadn’t considered until now. Your friends will likely have different answers, so you can see the variety of your missions. Take it one step further, said Vogels, and “consider how you could contribute to making that change happen yourself.”

9. If you could be a fly on the wall listening to any conversation, which conversation would you choose to hear?

What went on behind closed doors that you’d have loved to have known about? What exciting plans, what world-changing launch? Perhaps something that would simply be funny to overhear. “This scenario reveals our role models,” said Vogels. “It gives us the people we most want to imitate.” Eavesdropping isn’t the plan but for this one thought experiment, it’s okay.

10. If you could borrow one trait from any animal and use it to upgrade our species, which trait would you borrow?

The roar of a lion, the speed of a cheetah or the chameleon’s ability to blend in? “Underlying this question,” said Vogels, “is a reflection on what’s missing inside yourself.” It hints at the part you want to upgrade. Understand the deepest desires of you and those around you with help from the animal kingdom, no psychotherapist needed.

Ten scenario questions, developed by psychologists, to help you understand yourself and connect with others. Spark mini-coaching sessions and understand your friends and colleagues on a different level. Keep the conversations fun and open and see where they lead.

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