S6:E2 What Am I Missing? Leading Through Change with Jeff Messer

What happens when ten years of experience tells you one thing and someone on your team sees it differently? On this episode of Timeout with Leaders, cyber risk leader Jeff Messer shares how asking better questions helps leaders build trust and guide teams through change. He also reveals the sales skill he still uses to make cybersecurity risks feel real to the people making business decisions. What am I missing is a great question for each of us to ask ourselves, to stay grounded, present and willing to grow perspective. We don't have to have all the answers!

One Win at a Time | Nathan Hunstable, CIO of CEC Entertainment What happens when you lead with conviction, embrace vulnerability, and refuse to be anyone but yourself? We're kicking off a new season of Timeout with Leaders with Nathan Hunstable, CIO of CEC Entertainment, whose energy, authenticity, and passion for people are hard to miss. Nathan reminds us that great leadership isn't about having all the answers or the title behind your name. It's about showing up, building trust, and creating opportunities for others to succeed. Join us for a refreshing conversation about the human side of technology leadership, the courage to be yourself, and why sometimes success starts with just one win at a time. 🎙️ Welcome back to Timeout with Leaders. Let's get into it!

In this episode of Timeout with Leaders, hosts Kevyn and Tyler sit down with Andrew Wilder, the Chief Security Officer at Vetcor. With over 18 years of experience at a global giant like Nestlé, Andrew shares his journey of transitioning from a high-pressure corporate environment to a leadership role that prioritizes family and human connection. The conversation dives deep into: Modern Leadership: Why Andrew shifted from being a "technical manager" to an empowering leader who embraces failure and "crazy ideas." The Human Element in Tech: A candid discussion on the impact of AI, the importance of "presence" in a digital world, and why the next generation should consider both high-tech and skilled trades. Life Lessons: Andrew shares the powerful impact of the poem "A Father’s Lament" and how it reshaped his relationship with his children. Cybersecurity & Boards: Practical advice for new CSOs on how to present effectively to boards using the "noses in, fingers out" philosophy.

What if fear isn’t the thing holding you back… but the signal that you’re exactly where you need to be? In this episode of Timeout With Leaders, Tyler White and Kevyn Rustici sit down with entrepreneur, creative, and visionary Ray Myers — a man who’s built multiple businesses, stepped into acting, music, and even storm chasing. But this conversation goes deeper than credentials. It’s about the internal battle every leader faces. Ray breaks down the mindset shift that separates those who stay stuck… from those who move forward anyway: 👉 Run toward the danger. From overcoming self-doubt to leading through uncertainty, this episode unpacks the real work behind confidence — not motivation, not hype, but action. In this episode, you’ll learn: Why fear disappears the moment you take action How to reprogram your inner dialogue The truth about entrepreneurship no one talks about The difference between passion and purpose How great leaders handle uncertainty and pressure Why most people fail before they even start Confidence isn’t something you wait for. It’s something you build — one action at a time. ------ Connect and Follow 👉 Subscribe on YouTube for full episodes and clips Timeout with Leaders Podcast 👉 Connect on LinkedIn for more leadership insights https://www.linkedin.com/company/timeoutwithleaders/ If this episode gave you value: Follow the podcast for more real conversations with leaders Share this episode with someone building their career Leave a review to help us reach more people #TimeoutWithLeaders #Leadership #Entrepreneurship #Mindset #Confidence #OvercomeFear #GrowthMindset #HighPerformance #Podcast #BusinessPodcast #RunTowardTheDanger #SuccessHabits

What does it take to lead with discipline, resilience, and purpose across every season of life? In this episode of Timeout with Leaders Podcast, we sit down with Phil McKibbin, a leader whose journey spans elite athletics, service aboard a nuclear submarine, and executive leadership in professional sports. From lessons learned through pressure-filled moments in the military to building a 30-year career in technology leadership, Phil shares what it really takes to grow, lead, and stay grounded. This conversation goes beyond business. It is about character, consistency, and becoming the kind of leader others can trust. In This Episode, You’ll Learn: Why discipline beats motivation every time How to lead without needing a title The mindset required to grow into leadership Lessons from high-pressure environments How faith and daily intention shape leadership Why This Matters? Leadership is not built overnight. It is built in the unseen moments. The extra hours. The hard decisions. The choice to lead with integrity, even when it is difficult. If you want to grow as a leader, this episode will challenge how you think and how you show up. Connect and Follow 👉 Subscribe on YouTube for full episodes and clips Timeout with Leaders Podcast 👉 Connect on LinkedIn for more leadership insights https://www.linkedin.com/company/timeoutwithleaders/ If this episode gave you value: Follow the podcast for more real conversations with leaders Share this episode with someone building their career Leave a review to help us reach more people #Leadership #PhilMcKibbin #TimeoutWithLeaders #BusinessPodcast #Entrepreneurship #GrowthMindset #HighPerformance #LeadershipDevelopment #Resilience #Discipline #FaithAndLeadership

In this episode of Timeout with Leaders, we sit down with Carlton Dossman, Corporate VP at Microsoft. Carlton shares a leadership philosophy centered on harmony over balance, emphasizing being mentally present for the moments that matter in both family and business. From his early sales days at ADP to executive leadership at SAP and Microsoft, he reflects on the shift from individual performance to empathetic, high-impact leadership. He highlights the importance of constant reinvention, learning agility, and staying curious in a rapidly evolving world. Carlton also discusses leading at scale through trust and accountability, focusing on the what and why while empowering teams to own the how. Ultimately, he defines success through legacy—creating meaningful impact as a mentor, leader, and role model for his family and the thousands he leads.

Unlock the secrets of mental toughness and spiritual growth with Jim Rose, VP of Operations at Pilot Flying J. This episode serves as a masterclass in resilient leadership, challenging the idea that we are victims of our environment and proving that true power lies in mastering the internal landscape. Key Insights Include: Mind Over Circumstance: Why elite leaders focus on controlling their internal response rather than trying to manage uncontrollable external variables. The Vulnerability Accelerator: How embracing transparency and doing "hard things" fosters deep interdependence and builds unbreakable trust within teams. The "Crack in the Earth" Analogy: A practical framework for navigating tough conversations and resolving conflict before it scales into a crisis. The Power of Solitude: Why intentional isolation and mindset shifts are necessary tools for nervous system regulation and personal transformation. Conquering the Plateau: Strategies for maintaining a growth mindset when progress feels stagnant and using discomfort as a catalyst for dreaming bigger. Whether you’re a high achiever feeling stuck or a leader looking to fortify your team's culture, Rose’s blueprint emphasizes that resilience is a practiced discipline. Listen now to discover why pushing past your comfort zone is the only way to align your performance with your potential.

Redefine the essence of influence with Aftab Banth, founder of Deep Trail and former security leader at TikTok. This episode dismantles the myth of leadership-as-control, offering a roadmap for transitioning from high-stakes executive pressure to a leadership style rooted in inner peace and radical self-awareness. Key Insights Include: Regulated Leadership: How mastering your internal emotional responses transforms leadership from a dictatorial exercise into a source of calm, steady impact. The Vulnerability Pivot: Lessons from Banth’s transition from the tech C-suite to purpose-driven mentorship, proving that authenticity is a leader's greatest asset. Micro-Acts of Legacy: Why small, intentional acts of kindness and community support create a ripple effect that far outlasts professional ego or titles. Tactical Mindfulness: Practical habits for staying grounded—including reflective thinking and presence—that allow you to lead with clarity even in high-chaos environments. Beyond the Transactional: Shifting your focus from surface-level success to emotional intelligence, ensuring your influence is felt both in the boardroom and your personal life. Perfect for the leader tired of traditional power plays, Banth’s philosophy serves as a guide for those ready to lead with purpose, empathy, and genuine fulfillment. Listen now to learn why the most important person you will ever lead is yourself.

Step into the dojo and the executive suite with Amir Khawaja, Senior Director at Discover Financial Services and co-founder of Black Belts and Boardrooms. This episode explores how the discipline of martial arts provides a high-performance blueprint for corporate leadership, resilience, and emotional intelligence. Key Insights Include: • The Sparring Mindset: How the physical adaptability required on the mat translates into confidence and quick decision-making under corporate pressure. • Trust Through Mastery: Why delivering your best work is the ultimate foundation for building organizational trust and professional influence. • The Power of Limitations: Understanding how self-awareness and acknowledging your boundaries can actually become your greatest leadership strengths. • Tactical Mindfulness: Simple, grounding habits—like daily journaling and overcoming negative self-talk—to maintain clarity amidst organizational chaos. • The Empathy Edge: Balancing technical competence with humility to lead teams with authenticity and mental agility. Whether you are a seasoned executive or an aspiring leader, Khawaja’s philosophy demonstrates that true mastery is a holistic pursuit of mind, body, and spirit. Tune in to learn how to bridge the gap between physical discipline and professional excellence.

Dive into the career journey of Zach Lewis, CISO and CIO of the University of Health Sciences and Pharmacy, as he explores the intersection of technical resilience and the "human" element of leadership. This episode serves as a tactical guide for navigating the high-stakes world of cybersecurity while staying grounded in curiosity and connection. Key Insights Include: The Power of Curiosity: Why inquisitive hiring is the secret to building high-performing, adaptable teams. Ransomware Reality Checks: Lessons from Lewis’s book, Locked Up, on surviving a cyber crisis and coming out stronger. AI’s Educational Shift: Understanding how emerging tech is reshaping the classroom and the future job market. Combating Burnout: Practical approaches to sustaining a long-term career in a high-pressure industry. Whether you're looking for leadership strategies in tech or a firsthand account of surviving a ransomware attack, Lewis’s blueprint emphasizes that professional success is built on a foundation of authentic relationships. Listen now to discover why intellectual curiosity is the ultimate asset for the modern C-suite leader.