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

Vision, decisions, and leadership clarity—the ingredients for a team that executes, trusts, and innovates. 

In this episode, Damon invites Ross Romano—leadership coach, communications expert, and co-founder of the Be Podcast Network—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, “third 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. 

In this episode, you’ll learn:

• Why moving from “vision” to “decision” trips up even seasoned leaders—and how to fix it 
• The three “cons” of trustworthy leadership (conscientiousness, constancy, consistency) 
• A simple method for finding and refining your organization’s value proposition 
• How to escape the “should 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 out—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 

Timestamps: 

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 “third 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 leave—leadership and burnout 

42:15 – Ross’s magic wand: public opinion and resources in education 

47:27 – Community in schools—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.  

Resources & Mentions: 

• Ross Romano’s LinkedIn 
• Ross’s Show: The Authority  
• Ross’ Show: Sideline Sessions. 
• Book: Decisive by Chip & Dan Heath 

Podcast Contact Information: 

Website: www.learnit.com 

Email: podcast@learnit.com 

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