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The Essential Entrepreneurial Skill: Initiating Conversations

Recently, I've finally started breaking out of my comfort zone. Instead of waiting until everything is perfectly prepared to have coffee chats with others, I now proactively reach out whenever I feel there's a resonant topic or something worth discussing.

From Corporate to Entrepreneurship: The Communication Shift

For entrepreneurs, this is a crucial skill. In corporate jobs, who you communicate with is often arranged by your boss. But in entrepreneurship, you must proactively expand boundaries and initiate conversations. Whether it's with software developers or potential customers, you need to genuinely listen to their needs and understand what product features they want.

The Importance of Small Talk

Small talk ability is especially important here. It tests how quickly you can grasp the situation, understand emotions, and how to start a conversation. There are two key points: you can't make people uncomfortable, and you need to keep the conversation flowing smoothly.

I didn't have much training in this during my upbringing. In East Asian education systems, there's more emphasis on studying and exams rather than proactive communication and building trust. But after working on products, I realized this "natural familiarity" ability is essential. Whether it's customers, suppliers, or partners, if you don't proactively initiate conversations, they will never happen.

From Fear of Rejection to Taking Initiative

Initially, you might feel shy and hesitant to speak up. But based on my experience, once you've proactively arranged more than five coffee chats, you'll find it's not that difficult. The worst outcome is just being rejected, which is the same as not trying at all. Plus, there's still a 50% chance the other person will agree.

This way, you can not only get closer to customers but also gain deeper insights into industry trendsā€”information that's extremely valuable.

Practical Advice

Getting Started

  • Don't wait until "everything is ready" to begin
  • Take initiative when you have resonant topics
  • Start by practicing with five coffee chats

Communication Points

  • Genuinely listen to others' needs
  • Quickly grasp situations and emotions
  • Avoid making people uncomfortable while keeping conversations flowing

Mindset Adjustment

  • The worst outcome is rejection (same as not trying)
  • 50% success rate is worth the attempt
  • Every conversation is a valuable learning opportunity

Conclusion

In the entrepreneurial journey, proactively initiating conversations is not just a skillā€”it's an essential mindset. The transition from passive waiting to proactive action, from fearing rejection to enjoying the communication process, is a necessary path for every entrepreneur.

Remember: if you don't proactively initiate conversations, opportunities will never come your way.