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231: How Great Leaders Make Tough Calls (And Sleep Like a Baby After) | Ross Romano

Release Date:Μύ

October 20, 2025

Release Date: Oct 18

Vision, decisions, and leadership clarityβ€”the ingredients for a team that executes, trusts, and innovates.

In this episode, Damon invites Ross Romanoβ€”leadership coach, communications expert, and co-founder of the Be Podcast Networkβ€”into the Learn-It-All hot seat for an honest conversation on leading with values, making tough calls, and helping teams get unstuck. Ross shares stories from his coaching work with startup founders, corporate leaders, and education professionals, revealing why organizations falter (hint: it’s not always about execution) and how matchmaking between vision and action creates lasting results. Together, Damon and Ross break down value propositions, β€œthird options” beyond binary thinking, and the three key traits every leader needs to build trust and loyalty.

From defining clarity in chaotic industries to the unique burnout and motivation challenges facing education leaders, this episode is packed with actionable tools, candid advice, and inspiring stories for anyone facing a high-stakes leadership pivot.

What You’ll Learn:

  • Why moving from β€œvision” to β€œdecision” trips up even seasoned leadersβ€”and how to fix it
  • The three β€œcons” of trustworthy leadership (conscientiousness, constancy, consistency)
  • A simple method for finding and refining your organization’s value proposition
  • How to escape the β€œshould I stay or should I go” trap with creative career pivots
  • Why not losing passion, but feeling unable to make a difference, drives education pros outβ€”and how leaders can change that
  • Ross’s playbook for empowering teams as organizations scale
  • How the Be Podcast Network builds impact and connection in education and leadership communities

In This Episode:

  • 00:00 – Why you always reserve the right to change your mind as a leader
  • 01:28 – The challenge of translating vision into decisions
  • 03:43 – Why most leadership mistakes start with a fuzzy vision
  • 05:50 – Step one: clarifying audience pain points and values
  • 08:53 – Finding real differentiators in a crowded market
  • 11:36 – How often organizations should reassess their value prop
  • 14:22 – Ross’s journey into education and impact
  • 18:12 – Corporate vs. education leadership coaching: core challenges
  • 21:28 – A β€œthird option” career coaching success story
  • 27:52 – The three traits of leaders people want to follow
  • 31:08 – Where leaders struggle most (and Ross’s surprising answer)
  • 33:36 – Founders, delegation, and letting go of control
  • 37:34 – Why education leaders leaveβ€”leadership and burnout
  • 42:15 – Ross’s magic wand: public opinion and resources in education
  • 47:27 – Community in schoolsβ€”and what we all can do better
  • 48:01 – Building and growing the Be Podcast Network
  • 55:08 – Ross’s proudest impact for startups and storytelling
  • 59:09 – Key takeaway: What if it works?
  • 01:00:20 – Where to connect with Ross Romano
  • 01:01:21 – Final thoughts: Advocating for yourself as a leader

About Ross Romano

Ross Romano is a leadership coach, communications strategist, and co-founder of the Be Podcast Network, a powerhouse of 50+ shows serving education and leadership audiences. With deep experience coaching mid-career professionals, startup founders, and enterprise leaders, Ross specializes in helping teams and organizations get unstuck by aligning values, vision, and team dynamics. He’s passionate about impact in education, coaching corporate pivoters, and building communities for changemakers. Μύ

Resources Referenced:

  • Ross’s Show: Μύ
  • Ross’ Show:
  • Book:

Want to Learn More?:ΜύΜύ

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