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Leadership Development

Leadership Development: Text
Sat on the Rocks

Rudy Massimo believes that Leaders need to demonstrate active, authentic and positive leadership. How leaders adapt to change will determine their organization’s success. Status quo is not an option. Leaders need a roadmap and the courage to navigate through the uncertainty. It requires a paradigm shift that will allow them to see challenges as opportunities. Rudy often says, “Leadership is the ability to see through roadblocks.”

Our associates have extensive experience working with senior leaders and their teams. We can deliver a one-day workshop, to multi-day retreats. Over the years, we have organized and led unique outdoor experiences to bring teams closer together, from a canoe trip to a day of rock climbing. Sometimes, the best thing a team can do is leave the office to gain a fresh perspective. 

Leadership Development: Text

"The world is a huge place. How will you know where you fit in unless you explore beyond your comfort zone."

Ernest Shackleton

Leadership Development: Quote

Leadership Development Services

Business Meeting

Leadership Coaching and Advising

We provide executive coaching to senior leaders and leadership teams. We act as advisors to key members of your organization to support your strategic direction, and help you make effective decisions that are future-oriented. 
If needed, we will conduct a team assessment to ensure that you have the right people and teams in place, and that they have complementary skills to be effective in their roles.

Outdoor Activity

Experiential Growth

Over the years, we have designed a number of customized adventure experiences for individuals, families and organizations. They have used adventure travel as a unique and exciting way to raise funds for schools and charitable organizations, bring families closer together, or simply offer an opportunity to experience a new adventure. We offer customized executive and family expeditions. Through the integration of hands-on experiences and leadership skills development, we can design an expedition created uniquely to build skills and increase growth. Previous trips have ranged from climbing expeditions up Mt. Kilimanjaro, dog sledding in the Yukon, canoe tripping in Northern Ontario to a cycling adventure in British Columbia. The types of adventures we can organize for you have no limits.


Interim Leadership

We offer interim leadership solutions to support your organization through periods of crisis and transitions. In some cases, it is wise to bring in an interim leader after a longstanding executive has retired or moved on. It allows your organization to do a proper audit and determine the skills and experiences you are looking for in your next leader, knowing that an experienced leader is in place during this period of transition, which ensures stability.


Motivational Speaking

Rudy Massimo is a natural storyteller, leader and adventurer. He is a frequent speaker at international conferences. He speaks on topics related to education, leadership and philanthropy. He loves to share what he has learned from his time in the mountains, using it as a metaphor for dealing with change, uncertainty, and challenge.  Rudy has climbed and led expeditions all over the world, and he understands the dynamics required for teams to succeed. He will share his experiences…the good, the bad and the ugly. He will discuss the mindset that is required to deal with challenges in uncertain times, and why reframing challenges into opportunities can produce effective learning, actionable ideas, and innovative solutions. Some of his recent presentations have included:

“Achieving Top Performance”

“Importance of good governance”

“Leadership in Uncertain Times”

“Factors that contribute to highly effective organizations”

“Succession planning”

“Secrets of Major Gifts Fundraising”

“Leadership…and the keys to engaging employees”


Leadership Development: Services
Cave Hiker

"Before you are a leader, success is all about growing yourself. When you become a leader, success is all about growing others."

Jack Welch, Former CEO of General Electric

Leadership Development: Quote
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