Meet Alan Cahn
Executive Coach, Facilitator, and Pickleball Enthusiast
What makes working with you a unique experience?
Whether coaching one-on-one, leading a workshop, or facilitating training for hundreds, my goal is always to create an engaging and transformational experience. I ask thought-provoking questions that quickly get to the heart of the matter, inspiring leaders to take action on what matters most to them. My approach blends depth and light-heartedness, making the journey meaningful yet enjoyable.
What’s your coaching superpower?
I specialize in helping leaders achieve breakthrough results by disrupting limiting patterns and shifting their context. My clients often tell me that I help them connect to what truly matters, both in their leadership and their lives. I also bring decades of experience building high-performing teams, turning around struggling operations, and designing lasting processes.
What’s your background?
Education: Bachelor of Science in Social Inquiry from MIT.
Specialized Training: Post-graduate expertise in strategic design, business management, practical philosophy, and neuroscience-based approaches to change.
Experience:
Over 35 years in senior management positions, training and mentoring over 500 leaders.
Successfully launched and grew operation centers for an international training company while transforming underperforming areas into thriving successes.
20+ years as an executive coach and trainer, working across industries like sales, healthcare, construction, hospitality, insurance, technology, AI, and energy.
Who influences your work?
I’m inspired by thought leaders like Otto Scharmer (Theory U), Thomas Hübl, and Wendy Palmer. Their insights inform how I coach, helping me guide leaders toward clarity and meaningful change. I’m reading The Corporate Mystic and The Way We Are Working Isn’t Working.
What motivates you as a coach?
I’m passionate about helping people identify and overcome the barriers they don’t even realize are holding them back. I aim to ensure my clients achieve their learning objectives and create environments where those around them feel valued and supported. I pay close attention to what isn’t being said, uncovering hidden limitations and unlocking untapped potential.
What’s your proudest accomplishment?
I’ve helped an AI start-up articulate its mission, vision, and values—and live by them. I worked with a senior manager who went from struggling to thriving in under a year. And I supported an overworked leader in balancing his professional performance while starting to coach his son’s soccer team. Seeing my clients succeed in ways that bring both fulfillment and results is what drives me.
What’s life like outside of work?
When I’m not coaching, you’ll probably find me hiking in the Pacific Northwest, whipping up something delicious as my family’s chef, or enthusiastically playing pickleball. I’m an avid traveler—I visited four continents in 2024 alone and constantly seek new adventures.
What’s one thing people don’t know about you?
I was at Woodstock in 1969 and later lived in a Zen monastery. Those experiences shaped how I approach life, leadership, and the importance of staying grounded while embracing change.
What’s your leadership philosophy?
I believe a leader’s most significant accomplishment is enabling those around them to succeed. To me, the best leaders are the ones who, when the work is done, hear their teams say, “We did it ourselves.”
DID YOU KNOW?
I am an early adopter - I was at Woodstock, lived in a Zen Monastery in my early 20’s, and have been looking for more and more effective ways to contribute to humanity ever since. I am a “work in progress” (as we all are) and live my life knowing the best is yet to come.