How to Be a Great Conversationalist

At what age do we learn to have better conversations with others? At what age do we learn to have better conversations with ourselves?

Better conversations involve meaningful connection. They can be invigorating. And they can help us recognize our shared experiences, as well as the diversity of perspectives that make the world an interesting and confounding, place.

But better conversations can also be scary. They force us to get real with ourselves and others, real quick. Starting, and especially maintaining, a great conversation takes patience, practice, and skill. In our current world, where sound bites often gain more traction than substance, knowing how to converse in a meaningful way can feel like a lost art.

The good news is we can learn to be a better conversationalist at any time, and anywhere we happen to find ourselves…as long as we are willing to employ a few helpful strategies.

1. Know why you are talking

We generally communicate because we are trying to manage information (give or get more information), or we are wanting to influence others (to either begin/stop doing something). So great conversationalists always know why they are conversing, and they are self-aware enough to know that the other person also has a goal in the conversation as well.

2. Be intentional with your message delivery

Shifting from ‘auto-pilot’ mode to self-awareness mode means being intentional with your message by looking at your content (what you say), and your delivery (how you say it). Content that is intentional uses clear sentences with short descriptions, and involves the speaker communicating from their own experience by by using “I statements.” Delivery that is intentional involves an awareness of emotions, body language, tone of voice, and the level of trust in the relationship.

To be more intentional with your message, and to have that message received as you intended, it helps to ask yourself a few questions:

  1. What am I wanting to think, feel, do, and be after this conversation?
  2. How will the other person think, feel, do, and be after this conversation?

3. Practice concentrated listening

Concentrated listening involves listening with mindful awareness to what the other person (or our inner selves) is saying. This is a skill that takes time and practice to cultivate as many of us tend to listen with only one ear, and anticipate a break in the conversation for when it’s our turn to talk.

To cultivate more concentrated listening of ourselves (inner listening) and others (outer listening), it’s actually less about ‘listening to’ and more about ‘listening with.’:

Listening ‘with’ means we listen with our whole bodies and not just our ears. This means looking directly at the person who is speaking. It also involves using our senses, such as intuition, to pick up non-verbal cues. We also try to place ourselves in the other person’s shoes and ask ourselves, “how must this person be feeling right now?” Read my blog article on the three strategies of effective listening here.

4. Cultivate curiosity

Being curious is what separates an okay conversationalist from a great conversationalist. When we get curious about others, it challenges us to focus our attention outward and to learn something new. Everyone appreciates feeling seen and heard, and when you are expressing curiosity to another person you are communicating you are interested in who they are and what matters to them.

The greatest way to cultivate curiosity is through asking questions. However, not all questions are created equal.

Close ended questions usually invite a one-word response…usually a ‘yes’ or ‘no.’ Leading questions are usually just vehicles to confirm what we already assume and usually begin with, “…don’t you think…?” But open-questions are the ones that invite connection and a response. And the best open-ended questions begin with the words ‘what’ and ‘how’ [Ex: What did that situation/relationship/experience teach you?). The best questions that cultivate connection also gain information about a person’s thoughts and feelings. They sometimes reveal a new perspective and invite an honest sharing of thoughts, feelings, and information.

Being a great conversationalist can feel a bit like a lost art. That said, with the above four strategies, and some patience and practice, we can tap into our communication abilities and have quality conversations characterized by meaningful connection. Learn more about developing your levels of self-awareness in conversations by checking out my article “Why Self-Awareness is Important in Conversations.”