055: Why Do We Struggle to Have Meaningful 1:1 Conversations?

In this solo reflection, Erik unpacks a persistent and nuanced leadership challenge: why so many people struggle with deep, direct, one-on-one conversations. Drawing from personal experience, client work, and even his marriage, Erik explores processing styles, conversational pressure, and how leaders can adapt to create more inclusive, thoughtful dialogue—especially in high-stakes, fast-paced environments.

❓ The Big Question

Why do so many people struggle to go deep in one-on-one conversations—and what can we do about it?

💡 Key Takeaways

• The pressure to “respond well” often overrides true listening and participation.
• Fast processing isn’t better—it’s just one style. Leaders must make space for diverse processing speeds.
• Asynchronous communication (like Loom or voice memos) can unlock deeper, more thoughtful responses.
• Creating psychological safety includes honoring people’s preferred modes of reflection and response.
• Curiosity + adaptability = a powerful combo in meaningful conversation.

🧠 Concepts, Curves, and Frameworks

• Processing Style Awareness: Some people thrive on-the-fly; others need time to reflect. Know the difference.
• Asynchronous Dialogue Design: Tools like Loom and voice notes support thoughtful exchange without time pressure.
• The “Need to Respond” Trap: When people focus on what to say next instead of listening, conversations stall.
• Rules of Engagement Questions: Asking how someone prefers to communicate or process can be a game-changer.
• Spoken vs. Written Fluency: Most people communicate better verbally—but tone and facial expression matter.

🔁 Real-Life Reflections

• Erik’s marriage taught him how different processing styles can create or dissolve conversational friction.
• He’s learning to notice when someone disengages—not as resistance, but as a signal they need more space.
• Leaders often assume people should “just speak up”—but many need the right conditions to fully show up.

🧰 Put This Into Practice

• Ask team members: “How do you best process things—on the fly or with reflection time?”
• Test using Loom or voice messages for complex or sensitive topics.
• Give others the option: “Would you rather hash this out live or exchange thoughts asynchronously first?”
• Audit your 1:1s—are you giving space, or dominating the pace?
• Consider how your own processing style shapes your expectations of others.

🗣️ Favorite Quotes

“There’s a large portion of the population that wants to marinate before they give you their truth.”

“Just because someone can’t react quickly doesn’t mean their input isn’t valuable—it just comes differently.”

“Maybe the friction in your 1:1s isn’t resistance. It’s the pressure to participate before they’re ready.”

“Creating space is leadership.”

“We’re better speakers than writers—but we rarely design for that truth.”