Ask deeper questions to create connection

How often do our teams, family members, or collaborators end up misunderstanding each other even when we think we’re being perfectly clear? In this episode, we dive into the high cost of miscommunication and what it takes to become a “super communicator” in a noisy, divided world. We’re joined by Pulitzer Prize-winning journalist Charles Duhigg, whose new book “Supercommunicators” unlocks why our conversations so often miss the mark—and offers a toolkit for breaking through confusion and building true alignment.

Together, we explore how clarity, empathy, and attention are more crucial than ever, especially as our workplaces and lives move online. From hospital handoffs to debates with Uncle Gary, we unpack the vital art of matching the right kind of conversation, listening deeply, and decoding the signals that don’t show up in written words. If you’ve ever walked away from an exchange realizing you and your counterpart were simply talking past one another, this episode is for you.

Five Key Learnings from This Episode:

1. Assumptions are the enemy of understanding. We can’t assume others interpret our words as we intend; confirming mutual understanding is essential—even in routine exchanges.
2. There are three types of conversations—practical, emotional, and social. Misalignment around which conversation is taking place is often the root cause of frustration and disconnect.
3. “Matching” the conversation builds trust. Super communicators detect what kind of conversation someone needs and mirror it—acknowledging emotion when present, before pivoting to solutions.
4. Deep questions invite deeper connection. Asking about values, motivations, or experiences (rather than just surface details) opens the door for more meaningful dialogue.
5. Non-linguistic cues are powerful—but different channels require different strategies. Tone, posture, and facial expressions matter, but in written or digital communication, politeness, clarity, and rereading from the receiver’s perspective become the superpowers.

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