Enhance your forum connection with our customized YPO Retreats, designed to also increase the impact and potential of the forum and walk away with “aha” moments.
The most powerful retreats go beyond great conversations. They help leaders see themselves differently, confront patterns that may be limiting them, strengthen important relationships, and make meaningful changes in how they live and lead.
Drawing on more than 20 years as a CEO, Jack's executive coaching practice, and the principles of Aliveness Mindset, Jack brings experiential exercises that combine self-awareness, vulnerability, practical insights, and personal accountability.
The goal is transformation: Insights that lead to different choices, stronger relationships, and meaningful action long after the retreat ends.
A Sampling of My Most Popular Retreat Exercises.
Every retreat is customized to the group's unique goals, challenges, and opportunities.
Aliveness Mindset
Defining Question: What brings out the best version of me, and how can I bring more of that person into my everyday life?
Based on Jack's book Aliveness Mindset, this signature retreat helps successful leaders reconnect with what makes them feel fully alive and bring that energy, presence, and purpose into how they live and lead.
Achievement and fulfillment don't always go hand in hand. Leaders can accomplish extraordinary things while losing touch with what makes life most meaningful.
Through powerful stories, reflection, and experiential exercises, participants revisit moments when they felt most alive and discover what those experiences reveal about who they are at their best. They examine the beliefs, habits, and identities shaping their choices and learn to live with greater intention.
Leaders leave knowing what makes them feel alive, who they want to become, and how to bring their best selves to their leadership, relationships, and everyday lives.
When leaders are fully alive, the people around them feel it. Their relationships deepen, their leadership strengthens, and their impact expands. This is Living All In.
Living All In: A Life Assessment
The Defining Question: How fuly am I living in the areas of life that matter most?
It's possible to build an extraordinary career while gradually drifting from the people, priorities, and experiences that make life meaningful. Success can quietly mask that drift.
The Living All In Assessment helps leaders take an honest look at their lives through the Six Pillars of Living All In:
Physical Energy: Health, vitality, strength, and recovery.
Relationships: Connections with the people who matter most.
Work & Contribution: Fulfillment, growth, meaning, and impact.
Time Alignment: How closely your calendar reflects your priorities.
Inner Life: Emotional well-being, self-awareness, joy, and presence.
Purpose & Meaning: Values, faith, service, and legacy.
Participants discover where they're thriving, where they're operating on autopilot, and which areas deserve greater attention. Honest reflection and meaningful conversations reveal gaps between what matters most and how they're actually living.
Leaders leave with a clearer picture of their lives, renewed priorities, and specific commitments to invest more intentionally in what matters most.
Leading All In: A Leadership Assessment
The Defining Question: How am I leading, and who does my team need me to become?
The demands of leadership can make it difficult to recognize the behaviors shaping a team's performance, trust, and culture.
Leading All In challenges leaders to look beyond what they're accomplishing and examine how they're showing up .
Participants explore their purpose, presence, courage, ownership, decision-making, and ability to develop others. Where am I empowering people, and where am I creating dependency?
What difficult conversations am I avoiding? What might my team experience differently if I changed how I lead?
Through candid reflection, leaders identify strengths, uncover blind spots, and recognize behaviors that may be limiting their effectiveness.
Leaders leave with greater self-awareness and specific commitments to build stronger teams, increase ownership, and lead with greater courage and intention.
The Drama Triangle
Defining Question: When I'm triggered, who do I become, and what does it cost me?
Even effective leaders fall into reactive patterns under pressure. The Drama Triangle reveals three common roles: Victim, feeling powerless; Villain, blaming others or themselves; and Hero, rescuing and taking responsibility for others.
A leader takes work back rather than developing an employee. A team blames another department. Someone feels stuck, waiting for others to change. These patterns drain energy, weaken accountability, and keep problems repeating.
Participants recognize their triggers, understand what feels threatened, and learn to shift from automatic reactions to conscious choices. Through the Empowerment Triangle, they practice becoming Creators, Challengers, and Coaches.
The impact: Less blame and rescuing, greater ownership, stronger accountability, and more productive relationships at work and at home.
The Enneagram: A Powerful Tool for Self-Awareness and Leadership Growth
Defining Question: What unconscious patterns drive my behavior, and how might they be limiting me?
Many of the qualities that make leaders successful can also become their greatest limitations.
The Enneagram is a personality framework that reveals the underlying motivations, fears, and habitual patterns shaping how we think, feel, lead, and relate to others.
Participants discover how these patterns influence their responses to stress, relationships, decisions, and communication. They recognize strengths, uncover blind spots, and identify behaviors they can change.
The impact: Greater self-awareness, less reactivity, stronger relationships, and the ability to make conscious choices rather than being driven by automatic patterns.
The Enneagram is a foundational tool in my executive coaching practice, used extensively with CEOs and leadership teams.
A word from Jack:
"As a seasoned coach and YPO member since 2007, I specialize in empowering CEOs to lead with more clarity and decisiveness, enabling them to unlock their full creative potential. My deep understanding of the unique challenges faced by leaders, derived from years of moderating my own forum, allows me to offer targeted support to those committed to meaningful change and maximum forum impact."
Benefits of the program:
- Equip forums with strategies for authentic dialogue and practices for deep updates and meaningful presentations to achieve the greatest impact.
- Leave the retreat more energized about your forum and having greater personal and professional development and satisfaction.
- Forums leave equipped with multiple tools and practices to elevate their experience.
This offering is for you if you're:
- Interested in personal growth.
- Willing to be vulnerable and get to the 5% with your forum.
- Willing to get out of your comfort zone.
What you'll receive:
- A bespoke retreat intended to please every member.
- Exclusive exercises crafted by Jack, who utilizes the latest insights from thought leaders to create impactful activities.
- Opportunities to be challenged in ways that foster personal growth and development.
- A selection of Forum topics to choose from, including Aliveness Mindset, The Power of Regret, Creating An Inspiring 10-year Life Vision, The Enneagram Personality Profile, and more.
Learn more about working with Jack for your YPO retreat.
Interested?
Whether you're a seasoned leader or stepping into a new role, our offerings are crafted to energize your journey, infusing joy and purpose into every facet of your life.
"Thank you for your time and attention with our Forum. You helped us be better people, better husbands and fathers, better friends, and better leaders."
"Thank you for your thoughtfulness on so many fronts - the pre-surveys, pre-calls, nonstop day, and open door for all of us to connect with you going forward"
"I wanted to personally thank you for your expertise and the incredible way in which you share information and insight."
"Jack is an amazing retreat facilitator/coach. I personally admire that Jack never goes around something challenging or difficult."
"Jack led us on an amazing YPO retreat! He was committed, focused and caring. He created a safe space where all of us could comfortably dig deeper into issues that held us back."
