Scaling With People From Founder to CEO: The Messy Journey of Scaling Leadership with Aviva Leebow
Ever wonder what happens when your startup outgrows its scrappy beginnings? The transition from founder to CEO isn't just about a new title – it's a fundamental shift in how you lead, who you hire, and sometimes, the painful decisions about who stays on the journey.
Gwendolyn R. Curry sits down with Aviva Leebow, a Vistage Chair who coaches ambitious CEOs, to explore the leadership evolution necessary for sustainable growth. Their conversation dives into the uncomfortable truth that the people who helped build your company from nothing might not be the right ones to take it to the next level. They share strategies for having these difficult conversations while preserving relationships and respecting the contributions of early team members.
The discussion highlights a critical mistake most growing companies make: promoting skilled individual contributors without providing management training. "We do not train and coach people to become good managers," Curry notes, pointing out that leadership development remains the most overlooked investment in scaling organizations. Lebo emphasizes the importance of peer groups and external resources to help leaders grow beyond their current capabilities.
Perhaps most compelling is their exploration of founder self-awareness. Knowing when you've reached your leadership capacity – and being willing to surround yourself with experienced executives or even step aside – can be the difference between stagnation and continued growth. As Lebo shares through powerful examples, sometimes the greatest act of leadership is recognizing when someone else can better realize your vision.
Ready to evolve your leadership approach as your company scales? Listen now to gain insights that will help you navigate the messy, inspiring journey of growing with your business rather than just alongside it.