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HBO and The Ringer's Bill Simmons hosts the most downloaded sports podcast of all time, with a rotating crew of celebrities, athletes, and media staples, as well as mainstays like Cousin Sal, Joe House, and a slew of other friends and family members who always happen to be suspiciously available.
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When a team member keeps asking “why?”, it can feel like you’re dealing with a questioning attitude rather than simple curiosity. Those moments can be frustrating—but they’re also revealing. Most of the time, persistent “why?” questions point to something deeper: a gap in clarity, alignment, or vision.
In this episode, Scott unpacks why *the why* matters so much. The “why” is the **fuel of the vision**—it motivates your team, brings unity, and helps everyone understand the purpose behind every decision. When a leader doesn’t clearly and consistently communicate the why, people start to fill in the blanks themselves… and that’s when attitudes shift.
You’ll learn how to answer the why in a way that builds trust, how to discern when a question carries hidden frustration, and when to take the conversation private rather than addressing it in the room. Most importantly, we talk about leading proactively—*cascading vision, not just decisions*—so your staff feels informed, aligned, and supported before changes roll out.
We also walk through our team’s **Honesty Policy**, a framework for communication that creates trust, invites healthy conversation, and eliminates relational fog. It calls us to speak the truth “to the last 10%” in the right way, at the right time, to the right person. **We have zero tolerance for gossip.**
If you want a staff culture marked by clarity, unity, maturity, and trust, this episode gives you the tools to lead those conversations with confidence and calm.
⏱️ TIMESTAMPS
00:00 — When “Why?” Questions Become Something More
01:18 — Curiosity vs. Questioning Attitudes
02:08 — The Public Move: Answering the Why Clearly
03:01 — Why the Why Is the Fuel of Vision
04:15 — Casting Vision Instead of Cascading Decisions
05:10 — Preparing Your Why Before the Meeting
06:14 — The Private Move: Addressing Attitude 1-on-1
07:33 — Giving the Benefit of the Doubt First
08:42 — How to Use the Honesty Policy in Real Conversations
09:57 — “Last 10%” Conversations That Build Trust
11:21 — Questioning Spirit vs. Healthy Pushback
12:48 — When Misalignment Becomes a Grace-Lifting Issue
14:10 — Why You Must Address Small Problems Early
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