Jerry Colonna, CEO of Reboot.IO and author of 'Reunion,' is known for his transformative leadership insights. In this discussion, he emphasizes radical self-inquiry as key to breaking limiting patterns and fostering personal growth. He highlights the essential role of empathy in leadership and the significance of open, authentic conversations. Jerry encourages leaders to actively shape their organizational culture and create an environment of belonging, understanding, and shared experiences, making it a powerful guide for cultivating inclusivity.

Brian Gottlieb, author of Beyond the Hammer and a visionary business leader, scaled his startup from $3,000 to a $150 million enterprise. He discusses the art of hiring to your weaknesses, emphasizing the importance of filling gaps with talent. Brian shares insights on fostering a culture of continuous development and how to create scalable problem-solving systems that promote autonomy. Through personal anecdotes, he illustrates how empowering employees can lead to sustainable growth and a high-performing organizational culture.

In this discussion, Adam Coffey, a seasoned CEO with over 21 years in private equity, shares his journey from the military to leading successful service companies. He emphasizes the need for strong culture and transparency in leadership, introducing concepts like the 'Happy Meal effect.' Adam highlights the importance of adapting to growth stages, empowering teams, and ongoing self-improvement. His insights into performance management and fostering a collaborative environment provide valuable strategies for aspiring leaders to drive sustainable success.

Amy Edmondson, a Harvard Business School professor and expert in psychological safety, dives into creating safe environments for team members. She explains how psychological safety fosters innovation and learning, emphasizing its balance with accountability in high-performing teams. Amy shares insights on establishing clarity in organizational goals and the critical role of open communication. Using examples from Pixar and Southwest Airlines, she illustrates how to turn around fearful organizations and encourages leaders to embrace meaningful inquiry for better team dynamics.

Anthony Onesto, a visionary leader and founder of KAE.ai, dives deep into the distinct traits of Gen Z in the workforce. He highlights their craving for stability and proactive social engagement. The discussion shifts to the transformative power of AI in enhancing workplace efficiency. Anthony shares effective strategies for balancing autonomy with support in leadership, rethinking meeting culture, and the significance of understanding team dynamics. His insights into fostering a collaborative environment make this a must-listen for leaders aiming to adapt in a fast-paced world.

Eytan Bensoussan, CEO of NorthOne, shares insights on team motivations, effective hiring, decision-making with issue trees, feedback management, and building resiliency in entrepreneurship. He emphasizes gut instincts in leadership and practical strategies for empowering teams and strong leadership systems.

Matt Verlaque, COO of SaaS Academy, shares insights on building cohesive teams, effective feedback strategies, and creating unbreakable businesses. He emphasizes servant leadership, continuous improvement, and the importance of investing in people over tasks. Matt discusses adapting systems as companies grow, conducting one-on-one meetings, and structured quarterly planning for success in leadership roles and tech startups.

Mark MacLeod, seasoned CFO, VC, and angel investor, shares insights on CEO duties, avoiding burnout, and creating optionality for startups. He discusses the 24-hour decision rule, working on the business, and the importance of maintaining boundaries. Mark emphasizes self-care, time management, and building high-performing teams while balancing work and personal life as a CEO. His advice on risk-taking, authentic leadership, and redefining the CEO role make this episode a valuable resource for leadership skills.

Jessica Zwaan, COO of Talentful, discusses bringing product management practices and a commercial focus into HR. She shares insights on transitioning from HR to COO, structuring meetings for accountability, infusing product management practices into people ops, and fostering a culture of curiosity and innovation.

C-Suite executives from Tucows, DealMaker, Consensus, and Ably discuss innovative meeting approaches, remote work challenges, and the importance of structured processes for improving organizational productivity and decision-making. Insights shared on asynchronous communication, meeting policies, and transitioning to remote-first organizations.