About Us

What We Do

Our premier human development training service offers customized programs to enhance leadership,
communication, trust, teamwork skills, and productivity.

Coaching

Hybrid Leadership provides one-on-one and group coaching tailored to individuals and teams seeking personal growth and improved performance. Our coaching focuses on:

  • Building confidence and self-awareness.
  • Enhancing decision-making and communication skills.
  • Guiding leaders to navigate challenges with clarity and purpose.

Leadership Development

We specialize in helping organizations and small businesses cultivate strong leaders and cohesive teams. Our services include:

  • Customized workshops and leadership training programs.
  • Organizational assessments to identify areas for growth.
  • Strategies to improve team dynamics, communication, and trust.
  • Mentorship programs to empower emerging leaders.

Outdoor Education and Expeditions

Our unique outdoor education programs combine experiential learning with leadership development. Participants engage in adventures and challenges to foster growth, resilience, and teamwork. Highlights include:

  • Expeditions and nature-based educational events.
  • Leadership development programs for families, children, and corporate teams.
  • Activities designed to teach critical thinking, problem-solving, and collaboration.
  • Guided adventures that encourage personal reflection and connection with nature.

Why Hybrid Leadership Group?

In today’s fast-paced world, leadership isn’t just about authority—it’s about adaptability, trust, and the ability to thrive in any environment. Hybrid Leadership Group was built on the belief that true leadership is developed through experience, challenge, and connection. We take leadership beyond traditional classroom settings and immerse individuals and teams in real-world, hands-on experiences that foster resilience, communication, problem-solving and most importantly, trust.
Our unique approach blends leadership development, outdoor education, and experiential learning, creating tailored programs designed to push boundaries, strengthen teams, and unlock the human potential. Whether in the boardroom or the backcountry, we challenge individuals to step outside their comfort zones, fostering personal growth, stronger collaboration, and lasting impact.
With decades of leadership experience in military aviation, special operations, and business development, we bring an unmatched level of expertise to every engagement. From strategic coaching and team workshops to outdoor expeditions, our programs are custom built to equip organizations with the skills they need to excel under pressure and lead with confidence.
If you’re looking to build stronger leaders, develop a culture of trust, and create high-performing teams, Hybrid Leadership Group is your partner in leadership transformation.

About Bob Massey

Bob Massey is a leader who thrives where leadership, adventure, and human connection intersect.

As the founder of Hybrid Leadership Group, Bob brings over two decades  of leadership experience from military aviation, disaster relief response,, and joint special operations. A Senior Army Aviation Officer, he has led teams and organizations  in some of the most challenging environments worldwide, reinforcing his belief that leadership isn’t about rank or position—it’s about people, trust, and culture.

Bob created Hybrid Leadership Group to empower individuals and teams through immersive, experience-driven leadership development. His unique approach blends the importance of human connection with outdoor experiences, expedition leadership, and strategic coaching, helping teams build resilience, adaptability, and stronger connections—whether in the boardroom or the backcountry.

Bob’s academic foundation includes a B.S. in Commercial Aviation from the University of North Dakota and an MBA from the University of Montana. He has also completed executive education at the Stanford Graduate School of Business and the Tuck School of Business at Dartmouth, equipping him with the strategic insights to develop leaders and teams who can thrive in complex environments.

Beyond his military and leadership background, Bob is a graduate of the National Outdoor Leadership School’s Outdoor Education Course and a certified Wilderness First Responder, ensuring a deep understanding of risk management, decision-making, and team dynamics in unpredictable environments.

His philosophy is simple: if you get the people and culture right, you can change the world.

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How We Help Businesses and the Community

We partner with individuals and companies committed to making a difference in the world. Our Training Programs:

  • Individual Training
  • Leadership Development
  • Customized Workshops
  • Team Training
  • Expedition Guides
Join Us