Questions to Ask for Better Conversations

Every day we engage in conversations rooted in ritual and social norms. With no conscious effort, we shift from one role to another. One minute, I’m a husband happily cooking breakfast with his wife.

Shortly after, I’m meeting a client for lunch as a trusted advisor. And at the end of the day, I’m having cocktails with a friend as a confidant.

No matter who we’re interacting with, our emotions, wants, worries, and judgments are embedded in each conversation.

We mostly shape-shift on autopilot, giving no thought to our personal conversational patterns.

But when we pay attention to these patterns, we become more objective observers, reducing negative judgments about ourselves and others and creating space in our minds for navigating uncomfortable interactions.

Thirty years ago, I studied Voice Dialogue with Dr. Hal Stone and Sidra Stone. Voice Dialogue is the psychological concept of the internal self, developed through socialization.

According to the Stones, we adopt different personalities to cope with the vulnerabilities and complexities of life.

In every interaction, we must not only navigate the roles and words of others, but we must navigate ourselves. It’s no surprise that interactions go awry and confound us.

When I was young, I adopted a mediator self to navigate tensions within my family. To stop violence against my mom or sisters, I tearfully jumped into “let’s stop fighting” mode.

That coping mechanism served me well then, but later in life, I learned that it wasn’t always useful as a default pattern. When I needed to stand up for myself, I learned to adopt a confident and assertive persona, not a mediator.

The more I studied Voice Dialogue, the more I learned to appreciate emotional and social intelligence, self-awareness, and cognitive behavioral therapy because they all help us become more mindful of who we are and want to be in conversations.

By learning to focus our attention and practice, we can develop a centered aware presence and show up as our best selves.

To uncover the patterns of thinking that serve or hinder us in conversation, we can ask ourselves four questions.

Each question gives a window into conversational dynamics and patterns so we can better navigate confusing or fraught interactions.

1. What Roles Can You Observe in Your Interactions?

Each role we play with others involves intrinsic power issues, and real and perceived power dynamics play out, unspoken and unacknowledged. Those dynamics can enhance or hinder conversations.

An admired leader named Alicia recently attempted to understand a new team’s thinking about decisions on essential changes. She hoped to encourage them to think more deeply and creatively.

But her team interpreted her deep dive as an attempt to be a micromanager. The power they assigned to her voice created an unnecessary miscommunication.

In any conversation, ask yourself what role you are playing, and pay attention to the power dynamics. As a boss, are you coming off as arrogant or humble? As a direct report, are you presenting as judgmental or respectful? As a friend, are you critical or supportive? As a parent, are you fearful or loving?

Become a keen observer of your role, your personality patterns, and the inherent power dynamics of your interactions. Begin a practice of noticing without judging yourself. As a neutral observer, you can unhook from unhelpful patterns and consciously change your approach.

2. What Story Are You Bringing to the Conversation?

We thrive on the stories we adopted from our families and cultures. They facilitate connections, and when we hear stories that resonate with our patterns of thinking, our brains fire up. We experience neural coupling, an uptick of dopamine, and a positive shared experience.

No matter the role we play—mother, father, sibling, leader, or friend—every interaction is a complex collection of stories and potential connection.

Stories are vital, and unfortunately, they can also trap us in fear, worry, and conflict. Our emotions are a physical manifestation of our thinking. When someone opposes our beliefs, we can become emotionally triggered and react on autopilot.

I like the image of a spiral catching our triggers and reactions. At the bottom of the spiral are feelings of fear, contraction, and judgment. At the top are connection, love, and an open mind. The stories we tell and hear drive our emotions between those two extremes. An angry reaction is rooted in a story about unfairness, sadness is based on a story of loss, and so on.

Our stories help us navigate life, but we suffer when our ego is caught in their grip. We don’t have to give up our stories. We just have to be aware of them, recognize them, and consciously choose those that serve us and reject those that don’t.

Practice paying attention to your stories and how they are affecting others. Track them, listen to their voices, and watch yourself moving up or down the spiral. How would your thinking and emotions change if you didn’t accept your story as the truth?

3. What’s Fact vs. Fiction in a Conversation?

Our stories consist of facts and opinions. That might seem apparent, but fact and fiction become a perplexing, tangled web because our stories are so crucial to our identities, our egos, and the roles that we play. It’s not surprising that they often lead us astray.

Opinions, on the other hand, arise out of the collection of beliefs that we adopt throughout life. Unlike facts, our opinions are complex, personal, and uncertain. Our egos, roles, and personalities are very comfortable with our opinions, which comprise a big part of our thoughts. We readily defend them because we identify so closely with them.

But when we investigate our opinions, we slowly detach from them and reveal our more profound—and often unconscious—thoughts so we can make conscious choices about their value.

We can use four fundamental components of opinions—desires, concerns, authority, and standards—to transform our thinking, allowing us to change a difficult conversation into a collaborative one.

During a troubling conversation, ask:

• What desires and wants are part of this conversation?
• What concerns about the future are affecting my thoughts related to this issue?
• What power issues are impacting this conversation?
• What standards am I using to make this judgment?

What could you learn that would change your approach to a challenging interaction?

4. What Questions Can I Ask to Understand Others Better?

We unconsciously advocate for and defend our positions because we’ve long been trained to “have the answer.” Advocacy is far more common than its underappreciated sibling, inquiry.

To change that dynamic, begin to listen to how you and others advocate in conversations. What is your tone when you offer your perspective? When questioned, are you defensive or open to other ideas? How do you react when others advocate their position forcefully?

Instead of giving up our opinions, we can practice open advocacy. Closed advocacy is when we blindly attempt to convince others and defend our “right” answer.

Open advocacy is holding our opinions more lightly and sharing the thinking under the surface of our stories, creating space for deeper understanding.

Open inquiry is the art of asking sincere, respectful questions to seek understanding. It’s a secret key to creating mutual learning and collaboration. Good questions open minds and hearts, and they deepen conversations.

When we inquire about others’ desires, concerns, issues of power, and standards, we invite them into collaborative, creative interactions that are far more fulfilling than the alternative.

Practice being a better observer of the ways you and others advocate in conversation. Try defaulting to inquiry, rather than advocacy. You might be surprised at what you learn.

Asking these questions over time and observing your roles, stories, opinions, and interaction styles will dramatically increase your awareness and conversational skills and guide you to having more conscious satisfying conversations—and a little more peace.