231: How Great Leaders Make Tough Calls (And Sleep Like a Baby After) | Ross Romano
Release Date:
October 20, 2025
Release Date: Oct 18
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.
What 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
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 “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.
