This week on So Many Questions..., Kendall talks with author and designer Joshua Graves about why tough conversations are so hard, how kindness differs from “niceness,” and the tools we all need to navigate conflict with more clarity, compassion, and confidence.

Joshua shares stories from his upbringing in the South, how workplace dynamics and power structures shaped his communication style, and what he learned while researching and writing his book. They explore generational shifts in communication, boundaries vs. requests, and how to listen without losing yourself.

They also talk about mindfulness, trauma-informed approaches, why younger generations communicate so directly with leaders, and why giving yourself grace might be the most revolutionary practice you can adopt.

In this episode:• Joshua’s path from jukebox-obsessed kid to designer and author• How culture and power dynamics shape how we handle conflict• “Nice” vs. “kind” — and why the difference matters• Why difficult conversations feel so scary• How to listen with presence (without disappearing)• Setting boundaries that protect you• Generational shifts in workplace communication• Why many people fear talking to people in power• How to prepare for a tough conversation• What gives Joshua hope right now• Joshua’s powerful question of the week

About the book:
We Need to Talk: A Survival Guide for Tough Conversations offers practical, human-centered tools to help anyone approach high-stakes conversations without scripts, gimmicks, or forcing yourself into “fake” authenticity. A quick, accessible read packed with real stories and flexible frameworks.