How to Build Trust by Asking Powerful Questions

Jun 18, 2024

When trying to build relationships, it’s crucial to move beyond the standard “How are you?” and “What do you do?” Yet, many of us hesitate to ask more meaningful questions for fear of turning people off. So, how do you engage in deeper conversations without negative outcomes?

Understanding Perceived Risk

The fear of asking someone a “real” question is often magnified by our social conditioning. Our brains naturally seek comfort, which makes deviating from normative small talk seem risky. The worry is that the other person will be annoyed or that it will hinder the building of trust. However, this perceived risk is generally much higher than the actual risk. The worst-case scenario is typically just a brief uncomfortable moment—if someone dislikes a question, they might simply decide not to continue the conversation.

The Reality of Actual Risk

In reality, the actual risk of asking deep, genuine questions is quite low and, surprisingly, rare. I remember one instance when I was riding in an Uber and decided to engage the driver in more personal questions than usual. By the end of the ride, he expressed that out of the 7,500 rides he had given, I was the first person who made him feel truly heard. This reaction might not be universal, but it underscores the potential impact of taking a social risk.

The Importance of Taking Risks

As facilitators and leaders, it’s our responsibility to assume some level of social risk to foster meaningful interactions. If attempts to deepen conversation consistently fail, it might be necessary to reassess your approach. However, engaging in this kind of iterative dialogue often leads to surprisingly positive outcomes. For example, at a networking event, using name tags that invite people to share their favorite conversation topics can significantly lower the barriers to engaging in meaningful discussions.

So, I encourage you to take the leap—ask the deeper questions. You may find that 97% of the time, people are eager to discuss topics that truly matter to them. And who knows? You might just end up having a conversation about someone’s love for Pluto, despite it no longer being classified as a planet.