Gabe DeRita

Vistage Speaker | Relational Leadership Coach - Effective Connection, LLC | TEC Canada Speaker

Gabriel DeRita is a leadership and communication coach renowned for helping executives master crucial conversations, build stronger team connections, and achieve measurable improvements in collaboration and performance. With extensive experience coaching senior leaders from global Fortune 500 companies such as Airbnb, LinkedIn, Goldman Sachs, PayPal, Dropbox, and Gap, Gabriel brings proven strategies and actionable frameworks to every organization he supports. In a previous career, he held successful management and sales roles in the technology and tourism sectors, before hitting hard reset in 2018 to leave everything behind and live on a bicycle for a year to find deeper meaning and purpose. He found it in his current role, and Gabriel now dedicates himself fully to empowering leaders through executive coaching, interactive trainings and experiential workshops. His practical, engaging approach ensures leaders immediately gain tools they can apply to their toughest workplace conversations.

Gabe DeRita

Vistage Speaker | Relational Leadership Coach - Effective Connection, LLC | TEC Canada Speaker

Gabriel DeRita is a leadership and communication coach renowned for helping executives master crucial conversations, build stronger team connections, and achieve measurable improvements in collaboration and performance. With extensive experience coaching senior leaders from global Fortune 500 companies such as Airbnb, LinkedIn, Goldman Sachs, PayPal, Dropbox, and Gap, Gabriel brings proven strategies and actionable frameworks to every organization he supports. In a previous career, he held successful management and sales roles in the technology and tourism sectors, before hitting hard reset in 2018 to leave everything behind and live on a bicycle for a year to find deeper meaning and purpose. He found it in his current role, and Gabriel now dedicates himself fully to empowering leaders through executive coaching, interactive trainings and experiential workshops. His practical, engaging approach ensures leaders immediately gain tools they can apply to their toughest workplace conversations.

Gabe’s Topics

Every leader faces challenging conversations—whether providing tough feedback, addressing performance issues, or navigating interpersonal conflicts. Yet, the skill to engage effectively in these crucial dialogues can dramatically enhance team performance, strengthen relationships, and foster an organizational culture of openness and continuous improvement. In this highly interactive session, Gabriel DeRita provides Vistage members with a clear, structured approach for turning difficult conversations into opportunities for growth and clarity. Leaders will explore proven methods to prepare for and deliver feedback constructively, respond calmly when feedback feels uncomfortable, and build psychological safety within their teams. Members will practice real-life scenarios, reinforcing their learning through immediate application. Participants will leave empowered with practical tools and heightened confidence to handle their next hard conversation effectively and gracefully.