History

Phil has climbed, cycled, paddled and trekked thousands of miles across the U.S. and abroad compiling over 1,000 leadership field days with expedition-based organizations and private guide companies. He has worked in high-consequence environments leading tough populations where there is no margin for error and no days off; where people literally die from poor preparation, poor execution, or poor leadership. He has seen death first hand and has saved lives 

In 1995, following an unfulfilled career in finance, Phil began working part-time in the the outdoor education field and transitioned to full-time expedition leadership by 1997, while still managing his legacy clients until 2001. He brought the financial risk management strategies he learned from Wall Street with him to the backcountry, over time blending the unique risk challenges of both of these sectors into the proprietary Masterpoint.Strategies designed for deployment on the modern business landscape.

Phil has:

• Led at-risk and incarcerated men on remote, multidisciplinary, unsupported backcountry expeditions of over a month all over the United States

• Managed as many as five backcountry expeditions concurrently

• Recruited, trained and developed experienced and aspiring wilderness leadership professionals

• Created policies, procedures, and best practices for the adventure/experiential education sector

• Led field-based professional development courses for leading tech, finance, and pharma companies 

• Consulted on the Organizational Behavior module for a highly esteemed MBA program

• Written a book on high-performance team development and management which has been used in higher education

• Taught wilderness emergency medicine courses for extreme environments with austere resources

• Earned Viristar certification as a risk management professional

• Led incident reviews, safety audits, after-action reviews, and critical incident stress debriefing (CISD)

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Phil Bailey

Leading well-supported expeditions in iconic and hostile landscapes with the best industry training, willing and capable clients and all of the latest gear and equipment is probably one of the best incubators of learning and development regarding risk management and human performance, especially while under stress. But what is an even better pressure cooker to force and enforce those skills is leading un-supported expeditions in those same hostile landscapes with little training, clients who are forced to participate and have no relevant experience, and with gear that is suboptimal, insufficient, and often in need of repair. No contingency plan. No margin for error. The latter describes how I came up through the Adventure/Expedition Industry before eventually becoming a leader and consultant to one of the largest and most esteemed expedition and adventure education providers in the world.

I am not a typical business consultant and I don’t pretend to be. I am a pragmatic strategist focused on solving problems. I don’t have an MBA or Ph.D. I do not have industry recognized coaching certifications. I rarely wear a suit. I may not have the understanding of the industry design and jargon that consultants steeped in business experience may have. But that’s okay. That means I won’t assume I know everything. That means I will be genuinely curious about your business and your needs. That means that I may find blind spots which others may not. I won’t rely on the biases and standard business management tropes which may only be red herrings and slow the process of improving your operations or developing your people.

In the years I was in the field I learned more about crisis management, human behavior under stress, actual versus perceived risk, and the importance of identifying and understanding the factors and variables which define and drive these primary constructs of business success than I would have learned in decades of business management experience. An Ivy League MBA and years of experience in the C-suite of any Fortune 500 company can not anticipate and replicate the real world on-the-ground risk management, people management, and critical decision-making experience which I have been privileged to have. My experience and approach will not work for every situation or business type, but it may work for you. Let’s talk.