In this episode, I talk with Ethan Bull, President and Co-founder of ProAssisting, ranked No. 2466 on the 2025 Inc. 5000 list, about his innovative approach to delivering high-level fractional executive assistant services. Ethan shares how ProAssisting’s unique hiring and matching process connects leaders with exceptional EAs skilled in both strategic thinking and executive support. We explore the importance of mutual respect, curiosity, and clear communication in creating strong client-assistant relationships, as well as how these values reduce churn and drive success. Ethan also opens up about managing tough conversations and maintaining financial transparency and effective communication in his partnership with his wife, Stephanie. This conversation offers valuable insights for business leaders looking to elevate their leadership and maximize the impact of executive support.

6:41 Leadership Principles at Pro Assisting
13:12 The Role of Executive Assistants
16:28 Tough Conversations and Culture
23:47 Working Together: Business and Marriage
26:18 Conclusion: Insights on Leadership

Redefining Executive Support

In this episode, I sit down with Ethan Bull, Co-founder of ProAssisting, a company providing high-level fractional executive assistant (EA) services to businesses across the United States. We explore how ProAssisting differentiates itself from traditional virtual assistant services by focusing on top-tier talent capable of both strategic thinking and executive support. Ethan shares insights into their rigorous hiring process, emphasizing the importance of pairing clients with assistants who not only excel in administrative tasks but can also contribute to broader business strategy. This approach ensures productivity, long-term success, and meaningful partnerships between clients and their EAs.

Respect and Relationships

Mutual respect is at the heart of ProAssisting’s culture. Ethan discusses how fostering respect between clients and assistants leads to stronger collaboration, higher satisfaction, and reduced churn. He explains the value of emotional and interpersonal intelligence in executive support, sharing examples of how assistants who prioritize empathy and understanding create more productive relationships. By aligning expectations and cultivating trust, clients and assistants can work together seamlessly, driving growth and enhancing organizational performance.

Curiosity and Tough Conversations

Curiosity is a cornerstone of effective leadership and executive support. Ethan emphasizes how asking thoughtful questions and actively seeking to understand client needs strengthen communication and alignment. We also dive into managing tough conversations, including how assistants can “manage up” and navigate shifting priorities while maintaining context and empathy. By approaching challenging discussions as opportunities for growth rather than obstacles, both assistants and executives can enhance collaboration, improve decision-making, and create a more resilient work environment.

Lessons from Partnership

Toward the end of the episode, Ethan shares insights from co-founding ProAssisting with his wife, Stephanie. He reflects on the importance of financial transparency, open communication, and structured processes in both business and personal partnerships. Their experience highlights the challenges and rewards of working closely with family while maintaining professional boundaries. Ethan’s lessons provide practical guidance for business leaders looking to foster strong partnerships, whether with family, co-founders, or key team members, and underscore how these principles can enhance leadership effectiveness and organizational growth.

Key Takeaways

This episode offers a comprehensive look at how respect, curiosity, and open communication can elevate leadership, optimize executive support, and drive meaningful growth. Business leaders seeking actionable insights to refine their leadership style, strengthen client-assistant relationships, and maximize organizational impact will find this conversation particularly valuable.