Gavin Shaskolsky

Gavin Shaskolsky is a strategic, results-focused coach with over 21 years of experience partnering with leaders around the globe. He is deeply committed to transforming people capability, unlocking organizational potential, and helping leaders elevate their energy, clarity, and impact through powerful coaching conversations.

As Managing Director of GSI Coaching and Co-founder of Virtual Coaching Partners, Gavin leads and supervises international teams of over 60 coaches. He has coached more than 1,000 business leaders across 80+ countries and industries, including technology, finance, government, and retail. He’s been a trusted coaching partner to Microsoft since 2005 and has coached in the Microsoft LeaderPad program since its inception in 2010.

Gavin’s work is grounded in rigorous training, international certifications, and his own senior-level experience in business development, learning and development, and leadership strategy. A qualified attorney, he holds both a B.Bus.Sci and LLB from the University of Cape Town and has spent over two decades developing high-performing leaders and teams.

His coaching is known for blending fierce compassion, humor, realness, and presence—creating a space where clients feel both challenged and supported. He’s passionate about working with leaders who use their influence to make business—and the world—a better place.

Gavin’s Approach and Philosophy Around Coaching/Work

I’m committed to supporting, challenging, and helping people think well for themselves. I want the people I coach to feel courageous, vulnerable, and strong enough to follow their true path in leadership and life. I bring a blend of fierce compassion, curiosity, humor, and groundedness to my coaching that enables people to feel at ease—and at the same time, to stretch.

I pay close attention to the energy, tone, and atmosphere in the coaching space. I listen for what’s spoken and unspoken—on physical, emotional, mental, and spiritual levels. I believe that managing one’s energy is foundational to sustained performance, and I work integrally with each client’s whole system to support transformation that lasts.

Education / Certifications / Industry Experience

B.Bus.Sci and LLB degrees, University of Cape Town

• Qualified attorney with 20+ years in strategy, business development, and leadership

• Coach training: The Coaching Centre, South African College of Applied Psychology (SACAP), Process Work Institute, Internal Family Systems (IFS)

• Accredited Time to Think coach and facilitator

• COMENSA Master Practitioner (CMP)

• Certified in:

  • Insights Discovery

  • Heartstyles

  • ESCI (Emotional and Social Competency Inventory)

  • Korn Ferry Assessment for Leadership Potential

  • Harthill LDF

  • Benziger Thinking Styles

I'm Learning ...

I’m always exploring leadership, high performance, mindset psychology, and human potential. I love reading biographies, historical fiction, and books tied to my travels—currently diving into titles about Spain and Portugal ahead of an upcoming trip.

I’m a devoted Vipassana meditation practitioner and have meditated daily for over 26 years, often sitting annual 10-day silent retreats. This is my greatest teacher.

I’m inspired by the work of Arnold Mindell, Nancy Kline, Dick Schwartz, Otto Scharmer, and many others. I also stay plugged into coaching, leadership, and mindset podcasts, as well as ultra-running and current affairs.

I'm Proud Of …

Personal:

• Completing multiple ultra-endurance events, including 100-mile races and desert ultras

• Practicing daily meditation and serving as past chairman of the Vipassana Association of South Africa

• Being a father to my daughter, Ruby

• Surfing, running, and mentoring through organizations like Big Brothers International, Tsiba, Ort Jet SA, and The Mankind Project

Professional:

• Building a thriving coaching business, now 21 years strong, with 50+ coaches around the world

• Leading impactful coaching engagements for Microsoft and other global clients

• Coaching leaders who are creating meaningful, values-driven change in their organizations and communities

Did You Know?

I love running ultra-trail races through mountains and nature. I’ve completed multiple 100-mile races and two seven-day self-supported desert runs.