Crafting conversations for deeper connection

Two people sit under a tree on camping chairs watching a sunset and talking.

It takes skill and intention to treat others with the consideration they desire, and in today’s world, this understanding and effort have never been more important. At the heart of meaningful interactions and relationships is the recognition that everyone desires to be seen and heard – to be acknowledged and valued not just for what they do but for who they are.

David Brooks, in his enlightening book “How to Know a Person: The Art of Seeing Others and Being Deeply Seen,” responds to an epidemic of blindness (part of the loneliness epidemic) – an epidemic of not being seen or heard. This invisibility contributes to a society where sadness, rudeness, and fragmentation are becoming increasingly common. Brooks points out that true connection, the kind that counters this epidemic, involves social skills often left untaught and undervalued. He highlights that meaningful connection is vital not only for individual well-being but also for the health of our communities and societies at large.

Brooks introduces us to the concept of “question-askers,” a minority in our society, who possess the rare ability to make others feel special and understood through their genuine curiosity and attentive listening. This select group, comprising only about 30% of people, lights up others’ lives by inviting them to share their stories, thereby creating spaces of deep listening and engagement. This form of interaction is not just about passing time but about building connections that go beyond the superficial – it’s about recognising each other’s humanity.

Here are four of Brooks’ insights on creating good conversations, essential for fostering this deep connection:

1. Attention is an off/on switch, not a dimmer. True attention is an all-or-nothing commodity. In conversation, giving someone your full, undivided attention is foundational.

2. Be a “loud” listener. Show your engagement not just through silence but through affirmative sounds and gestures that convey you’re actively following and appreciating the other’s words.

3. Encourage storytelling. Don’t let the person you’re talking to remain a mere observer of their own story. Encourage them to dive deeper and share more, making them the author of their narrative.

4. Ask great questions. The essence of a good conversation lies in the questions asked. Great questions (or prompts) are open-ended, thought-provoking questions and encourage storytelling.

Here are some that he suggests for when getting to know someone more deeply (not necessarily what you would ask a complete stranger!).

  • Tell me your favourite unimportant thing about yourself.
  • If this five years of your life is a chapter, what is the chapter about?
  • What would you do if you were not afraid?
  • If we meet a year from now, what will we be celebrating?
  • What has become clearer to you as you have aged?
  • What’s working really well in your life?
  • How do your ancestors show up in your life?

He believes that asking such questions gets a person out of their daily life to look at bigger or deeper matters.

I have been working on some questions to ask of my own:

  • What happened last time you surprised yourself?
  • What’s the gift you have that is not getting fully used?
  • What have you said NO to recently with great conviction?
  • What idea have you changed your mind about recently?
  • If you could wave a wand and magically transform something in your world, what would it be?

In developing my own questions and prompts, I have set myself an intention to have two questions/prompts ready for conversation starters when I catch up with people. I extend that intention to mindfully and deeply listen for any vulnerabilities that might be present in the stories I hear. Additionally, I aim to ensure I am respectful and creating a safe space for people as they reveal more of themselves to me. I intend to be equally willing to reveal more of myself to them, as they get to ask me similar questions.

In the context of the Self unLimited philosophy, such conversations are not just about enhancing personal relationships but also about shaping your workscape relationships. By seeing and hearing others, we not only enrich our personal lives but also create a more meaningful, connected professional environment.

Every interaction is an opportunity to make someone feel seen and heard, to create a moment of connection that counters the root causes of the loneliness epidemic. David Brooks, says “great seeing is a creative act that changes relationships and might even change societies.” It’s about making the choice to engage with intention and depth, to see and celebrate the person in front of you. This is the path to a richer, more compassionate world.


What intentions will you set for yourself in crafting conversations for deeper connections in your workscapes?


Helen Palmer, Founder of Self unLimited, believes deeply in the power of connection and the art of meaningful conversation. By advocating for the practice of intentional listening and thoughtful questioning, she aims to foster workscape environments where individuals feel seen, heard, and valued. Through her work with Self unLimited, she encourages others to explore their own narratives and connect with the world in more profound and fulfilling ways.


(Amended) Photo by Harli Marten on Unsplash