Regardless of how much time is invested in reading, researching, and listening to some excellent communicators, it seems to me that communicating well will always be a challenging task. And as the journey continues in an attempt to equip Gen Z and emerging adults, the obstacle becomes even greater when recognizing the reality that although technology is creating a hyperconnected society, the art of conversation might be diminishing as a consequence.

As a recognized introvert, I do not always enjoy the banter of small talk but can relish opportunities for engaging conversations with others; however, I am frequently finding myself rather bored with attempted conversations with students. Whether this is a symptom of a generation who is uninterested in engaging in conversations with me and the topics I choose, or whether it is more symptomatic of our culture, I must voice concern over an apparent deficit in conversational skills. Granted my experiences may be unique, but if they are not, then those of us who currently have opportunities to influence emerging generations should consider becoming more intentional with our coaching in the art of conversation.

I offer that we consider how to instruct emerging adults in handling light conversations such as they might encounter on job interviews or in first-floor relationships where discussions typically revolve around news, weather, and sports to more in-depth conversations where they develop the essential skills of humble inquiry and listening well. Adding to these beginner level of conversations, I will also posit that we consider how to educate emerging adults on what John Ortberg has called courageous conversations. Current reading has led me to offer four categories of what I would describe as courageous conversations and they include challenging or tough conversations, empathetic conversations, lingering conversations, and the most important of all, spiritual conversations.

In Dare to Lead, Brene Brown acknowledges that many leaders are avoiding tough conversations that can be vital when offering honest, productive feedback. Expanding on this thought, Brown shares of Roosevelt’s ‘in the arena’ moments when we are called to courage and that daily practices are critical for supporting us in what Brown calls the rumble. “A rumble is a discussion, conversation, or meeting defined by a commitment to lean into vulnerability, to stay curious and generous, to stick with the messy middle of problem identification and solving, to take a break and circle back when necessary, to be fearless in owning our parts, and as psychologist Harriet Lerner teaches, to listen with the same passion with which we want to be heard.” So, if we desire to stand courageous in our conversations, we need to be willing to rumble with hard things.

In addition to engaging in the tough conversations, Brown appreciates the need for trust during those conversations which often surfaces through connection and empathy. Simon Sinek echoes the importance of empathy in Leaders Eat Last, when describing Special Forces Operations in Afghanistan and the critical role empathy had in serving as an asset to the pilots protecting troops on the ground. Sinek reminds readers that successful organizations where members are “willing to push hard and take the kind of risks they do” demonstrate this achievement often through empathy. Brown and Sinek inspire organizations to add “empathy to our courage toolbox” so that courageous conversations can take place because sometimes there are bad moments and “it’s not our job to make things better. It’s just not. Our job is to connect. It’s to take the perspective of someone else. Empathy is not connecting to an experience, it’s connecting to the emotions that underpin an experience.”

Once we’ve invested time instructing emerging adults in navigating the tough and empathetic conversations, we might focus our attention on how to linger with our conversations. Addressing this concern of modern society to hurry through our interactions, we might be wise to consider how to listen well, humbly inquire, and invest time so that lingering conversations become a more natural part of our routine.

Lastly, addressing one of the most important conversations critical to a flourishing life is the one Don Everts calls a “spiritual conversation” which is “a conversation with anyone about their faith or lack of faith (e.g. discussing the sermon, instructing your kids; learning why your friend doesn’t believe in God).” This essential conversation will be discussed in the next post, but I would like to offer the opportunity to increase the list here of the types of conversations you would consider courageous by adding to the comments below.