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I Have Some Questions...
Most people know the headline of a leader’s story. Few know the path it took to get there. This podcast goes beyond titles, book launches and business wins, to explore the lived journey behind the thought leader.
Through deep, unhurried conversations, we uncover the moments that shaped them—the doubts, pivots, convictions, and quiet breakthroughs that built their body of work.
Each episode features authors, coaches, executives, and bold thinkers who have forged their own path. Instead of rehearsed talking points, they’re invited into a space where thoughtful questions unlock something more human. The result is a layered conversation that reveals not just what they preach, but how they became the kind of person who can teach it.
Because we believe the best stories aren’t always told—they’re revealed. And when brilliant people are given the right questions and the room to answer them fully, what emerges is insight you can feel, frameworks you can apply, and a deeper understanding of what it truly takes to lead, create, and contribute at a meaningful level.
I Have Some Questions...
131: Steve Toomey: "Are You Asking to Understand, or to Respond?"
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In this long-awaited conversation, Erik sits down with longtime friend and mentor Steve Toomey to unpack the art of curiosity, the discipline of presence, and the quiet power of asking better questions.
They explore why interest fuels insight, how empathy can both strengthen and sabotage leadership, and what it really means to be “faithfully present” in a divided world. From boardrooms to Teen Challenge, from StrengthsFinder revelations to St. Francis’ prayer, this conversation weaves leadership, faith, humility, and self-awareness into a compelling invitation:
Stop trying to win the conversation. Start trying to understand.
👤 About the Guest
Steve Toomey is a seasoned business leader, former commercial real estate executive, and lifelong student of faith, culture, and human nature. Known for his thoughtful questions and relational presence, Steve brings decades of leadership experience—paired with humility and reflection—into every conversation.
His influence spans business, ministry, mentorship, and community-building, where he’s consistently focused on one thing: understanding people deeply enough to serve them well.
🧭 Conversation Highlights
- Why curiosity—not intelligence—is the foundation of a great question
- The tension between offering advice and asking one more question
- How empathy can become a leadership crutch if not paired with accountability
- What Steve learned from 40 years of marriage about “fixing” vs. understanding
- Why culture change doesn’t happen through laws—but through faithful presence
- The surprising leadership breakthrough Steve had late in his career
- How knowing someone’s story increases compassion (and reduces judgment)
- Why comparison quietly robs leaders of confidence and contribution
💡 Key Takeaways
- Interest drives insight. The quality of your questions often reflects the depth of your curiosity.
- Empathy without accountability leads to stagnation. Both are necessary for real leadership.
- Most excuses fall into predictable patterns. When you recognize them, you can redirect instead of react.
- Comparison distorts contribution. Your value often lies in the very differences you’re tempted to dismiss.
- Faithful presence beats grand gestures. Culture shifts slowly—through consistent relational investment.
❓ Questions That Mattered
- What actually makes a good question?
- Am I asking to understand—or asking so I can respond?
- Who am I trying to serve in this conversation?
- What story might I be missing about this person?
- Am I comparing myself out of confidence instead of leaning into my strengths?
🗣️ Notable Quotes
“There are certain people I don’t find interesting… and I don’t ask good questions when I’m not interested.”
“There are a lot of things that aren’t our fault—but they’re still our responsibility.”
“If you don’t know someone’s story, it’s hard to be compassionate.”
“The line between them and us is much thinner than you think.”
“Just be faithfully present. You don’t have to fix everything.”
🔗 Links & Resources