In my last newsletter, we talked about the importance of face-to-face conversation, and how critical it is to your success as a trusted advisor. We’ll continue that discussion by understanding the point of your conversations, and role context plays.

To become a master conversationalist, your starting point is straightforward, but perhaps not always simple: Appreciate the singularity of each moment in your conversations. Any moment in a conversation has an irreversible quality and historical importance in determining how that conversation will play out. How you respond to the conversation determines your role: protagonist or antagonist, hero or villain, supporting or opposing. Your response also determines how your client responds.

Every conversation is unique and represents a snapshot in time. Grasp the reality that this conversation—as it is at this very moment—will never present itself in the same way again. When you do, you realize that the dynamic nature of events and people does not allow for repeat performances. Be sure you take advantage.

Professor Diana Tamir, PhD reminds us that “during a conversation, it’s important to know where the other person is, but it’s also important to take them into a new direction—to say something that’s going to surprise and interest them.” Words that are said in the first take (constructive or destructive, thoughtful or flippant) will be remembered and woven into the fabric going forward. A master conversationalist understands the critical role of timing in any discussion—because timing influences context, emotion, and openness.

Here’s an example I shared in my book, Defining Conversations:

Terry, a business owner, sat down with a business associate to discuss forming a partnership. He couldn’t understand why his would-be partner, who had also become a friend, wasn’t keen on the idea—until his friend started talking about his pending divorce. He had grown pessimistic about any agreement and the overly optimistic promises that held them together. He was simply not in a place to enter any new partnerships at that moment. Without this context, Terry might have been offended, and their relationship would have suffered.

Try to ensure your conversations with clients explore context, not just content. This story illustrates the importance of asking ourselves how the conversation we are engaging in fits into the overall context of the other person’s reality. There may be a reason a client is pushing back on a recommendation.

According to M.I.T. Associate Professor Evelina Fedorenko, “Language is about getting meanings across, and that often requires taking into account many different kinds of information — such as the social context, the visual context, or the present topic of the conversation.” Defining conversations happen when they happen for a reason. Understanding the context and the specific timing is the first mission of the great conversationalist. You need to address a situation as it is in the moment; to do so requires appreciating how you arrived at a particular point. The following questions can help home in on the importance of a particular conversation:

  • “Why are we having this conversation right now and not a month ago, or a month from now?”
  • “How did I get to where I am? What events or circumstances have led me to this conversation?”
  • “How does this conversation fit into the bigger picture?”
  • “Should I be having this conversation right now?”

The goal is to understand the point. As alluded to earlier, heightened awareness comes with the realization that this exact scenario will never repeat itself again. This awareness leads to a raised esteem for what someone is saying and why. Does the other person feel the situation has gone too far, or are they trying to prevent something worse from developing? Are they worried, offended, hurt, or fed up? Do they see this situation as an indicator of future developments? The answers to these important questions are impossible to understand without hearing the contextual story that led up to this particular conversation. Put simply, you cannot discover the fruits of conversation until you first find their roots.

There are two timelines at play in every situation—one chronological and the other visceral. Both are important in determining where you are at in a particular conversation. The chronological timeline helps you understand the backdrop to the story, while the visceral timeline helps you understand your client in terms of emotion invested and emotion spent. Intuitively you will want to ask yourself if this conversation is happening at an emotional peak or nadir. If you are too early or too late on the visceral timeline, you (and your client) will probably not get the results you hoped for.

Understanding the contextual story and the emotional needs of your client constitutes your safety vest as you enter the waters of turbulent conversation. If a conversation revolves around some form of disagreement, negotiation, or injury, it becomes vital to guide your sense of curiosity toward comprehending that client’s context, story, and emotional need. You will rarely misstep in a conversation if you do so.

Blaise Pascal remarked that the branch can never grasp the meaning of the whole tree. Assume the tree represents the sum of your life and what it will become, and each branch represents your important and pivotal conversations. The fruit harvested from these branches are the resulting gains in relationships and outcomes from each conversation. It may be helpful to envision your next important conversation as a branch on your own tree of life.

The best conversationalist is fully present in each conversation. Being fully present begins with a curiosity around the genealogy leading to the particular conversation: “Why am I here right now? What led me to this point?”

When playing the role of responder in an important conversation, you might say, “This feels really important—you must have given this a lot of thought.” This response may flush out the timing aspect of the conversation and indicate where it fits into the larger scheme of things in your client’s mind. What you hear will help you determine exactly where that client is at in terms of events and emotions.

Understanding this context creates a layer of appreciation and consciousness, enabling you to bring a more agreeable sense of meaning to your conversations, as well as a sense of personal importance to the other party.

Ask yourself how your next client conversation fits into the larger picture of that person’s life and well-being, as well as your own. By doing your best to capture the meaning of the moment, you will discover the first point of conversation—timing and context, and the fact that this moment can never again repeat itself. This understanding naturally and gracefully moves you toward understanding the other person’s point of view.