COACHING
Leadership comes with distinct challenges. Whether aligning teams, driving strategic growth, or navigating organizational change, senior executives face critical decisions that demand both clarity and confidence. Benjamin Canyon Gass partners with senior leaders to navigate these challenges and create meaningful, lasting impact.
With 20 years of experience working in the social impact and private sectors, Benjamin brings a wealth of insight to his coaching practice, helping leaders clarify their vision, refine their strategies, and drive transformative results. As Founder of Conspire for Good, Benjamin has advised over 80 mission-driven organizations—including UNICEF, the Ford Foundation, NAACP, MoveOn.org, and The White House Office of Public Engagement under President Obama. Having conducted 360 leadership assessments for dozens of CEOs, he understands the unique needs of senior leaders and the complex dynamics in which they operate.
Benjamin’s extensive experience informs a coaching approach that blends strategic insight with practical tools. Working with him is an opportunity to elevate your leadership, inspire your team, and tackle challenges with renewed focus and effectiveness.
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As your coach and strategic partner, I blend leadership development with hand-on problem solving. Together, we’ll identify and overcome personal barriers, build resilience, and craft effective strategies to help you and your organization thrive.
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Empower Your Leadership
Your custom coaching program will be designed around your unique goals and needs for development, adapting as needed to challenges and opportunities that arise throughout our work together. Here are some areas of possible focus:
Strategic Leadership
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Leadership Challenges
Navigate organizational complexities, board relations, and strategic decision-making with clarity and confidence.
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Power Dynamics
Increase your effectiveness by refining how you leverage power— discerning when to assert authority and when to empower others.
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Delegation Mastery
Maximize your impact by focusing on critical tasks while driving effective decision-making and project ownership.
Personal Development
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Purpose Alignment
Clarify and embody your deeper purpose, using it as a foundation to inspire and guide your leadership journey.
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Personal Transformation
Overcome personal barriers, social conditioning, and psychological triggers to foster authentic, resilient leadership.
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Relational Dynamics
Improve challenging relationships by improving communication and building trust.
Organizational Effectiveness
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Communication Excellence
Articulate your vision with clarity and consistency, enabling effective execution by your team.
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Accountability & Consistency
Develop systems that make it easy to maintain accountability, ensuring you model the standards you set for your organization.
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Cultural Development
To attract and retain top talent, build a culture of open communication and feedback, where team members feel safe to express themselves.
Coaching Approach & Process
Our unique approach combines interview-based 360 assessments and cutting edge AI tools to create an individually-tailored roadmap for your development and enhance your coaching experience.
1 | Initial Consultation
Start your coaching journey with a complimentary 15-minute video call. This session is your opportunity to share your goals, challenges, and aspirations. Together, you'll explore what you’re seeking from coaching and how Benjamin can best support your growth. This is also a chance to ensure it's a good fit for a successful and transformative partnership.
2 | Assessment & Goal Setting
Before your first session, you’ll complete an intake form that delves into your goals and challenges. The first meeting will be dedicated to reviewing your responses, clarifying your priorities, and establishing actionable goals. This foundational step ensures that each session is focused and aligned with your personal and professional aspirations.
3 | Tailored Coaching Sessions
Your sessions, typically scheduled weekly or bi-weekly, are dedicated time to focus on your growth. Each 60-minute meeting is a collaborative space to address challenges, brainstorm strategies, and celebrate your progress. The coaching journey is flexible and adaptive, designed to meet your evolving needs, staying attuned to what’s most relevant and impactful for you at each stage. This dynamic approach ensures that every session delivers practical value.
4 | Feedback & Reflection
At the close of each session, we’ll reflect on your progress and the strategies we’ve employed. Your feedback will guide our approach, ensuring that coaching remains aligned with your goals. This iterative process enables us to celebrate wins, adjust where needed, and maintain steady progress.
5 | Homework & Action Steps
You’ll leave each session with actionable steps and practices. Whether it’s trying a new strategy, implementing a tool, or shifting a mindset, these action steps will help you bridge the gap between insight and transformation. Experimenting between sessions allows you to test ideas, build confidence, and sustain momentum.
6 | Asynchronous Support
In addition to regular sessions, you’ll have access to asynchronous support through email check-ins and curated resources. Whether you need quick guidance, motivation, or tools to address specific challenges, you'll feel supported every step of the way.
