Command Post Cohort

Craig and Andrew explore the distinction between leadership and expertise, emphasizing that while leaders should have a general understanding of their organization's operations, they do not need to be experts in every field. They discuss the importance of communication, trust, and collaboration in effective leadership, as well as the necessity of being present with team members to build relati...

Craig and Andrew discuss the concept of influence without authority, particularly in leadership roles. They explore the challenges faced by leaders in complex environments, such as military operations in Afghanistan, where building trust and navigating competing priorities are crucial. The conversation emphasizes the importance of listening, relationship building, and redefining success in collabo...

In this episode, Craig and Andrew discuss the challenges and responsibilities of leadership in the face of new tools and technologies, particularly artificial intelligence. They emphasize the importance of building a culture of trust within teams to navigate change effectively. The conversation explores how leaders can define success amidst uncertainty, enhance team performance with technology, an...

Summary In this episode, Craig and Andrew discuss the critical distinction between being busy and being productive, especially in leadership roles. They explore the importance of prioritizing tasks, managing time effectively, and incentivizing productivity over mere busyness. The conversation delves into the significance of metrics and outcomes in measuring success, emphasizing the need for leader...

Craig and Andrew discuss the evolving landscape of workplace policies, particularly the return to office debate. They explore the complexities of remote work, the importance of trust in teams, and the need for leaders to adapt their strategies based on the specific needs of their organizations. The conversation emphasizes the significance of intentional decision-making and clear communication in f...

This conversation discusses the critical aspects of leadership in high-risk military operations, focusing on the complexities involved, the importance of trust, communication, and planning, and how these elements contribute to successful outcomes. The speakers emphasize that effective leadership is not just about high-ranking officers but involves all levels of personnel working together to achiev...

In this episode of the Command Post Cohort, hosts Craig and Andrew kick off Season 2 by discussing the foundational elements of effective leadership, particularly focusing on trust as the cornerstone of high-performing teams. They introduce their upcoming book, which outlines a system designed to help leaders build trust through five key mechanisms: standards, communication, decision-making, plann...

Craig and Andrew announce their book being released in 2026 and share the audio from the live crossover podcast from the Monthly Military Connected Mentorship Meetup with special guest Brandon Cates CEO of Ametrine. www.commandpostcohort.com www.outsiders-group.com

Summary In this episode, Craig and Andrew explore the human side of leadership, emphasizing the importance of servant leadership, team dynamics, and the challenges leaders face in asking for help. They share stories and insights on how building relationships and trust within teams can enhance collaboration and operational effectiveness. The conversation highlights the need for leaders to recognize...

In this episode, Craig and Andrew discuss leadership lessons drawn from Andrew's military experiences, particularly focusing on the challenges faced during combat deployments. They explore themes of resilience, the weight of command, overcoming fear, and the importance of optimism in leadership. Through personal stories, they illustrate how leaders can navigate adversity and maintain a positiv...

In this episode, Craig Oglesby and Andrew discuss the concept of Commander's Intent as a leadership tool, emphasizing its importance in both military and business contexts. They break down the components of Commander's Intent, including purpose, key tasks, and end state, and illustrate how these elements empower teams to operate effectively and make decisions independently. Through real-wo...

In this episode, Craig and Andrew discuss the complexities of cross-functional leadership through a military operation story. They explore the challenges of communication, planning, and execution in high-stakes environments, emphasizing the importance of collaboration and understanding among different teams. The conversation highlights how miscommunication can lead to operational hurdles and the n...

In this episode, Craig and Andrew discuss the concept of breaking rules in leadership. They explore the idea of 'disciplined disobedience' as a necessary skill for leaders, emphasizing the importance of critical thinking and understanding the purpose behind tasks. Through real-world examples, they illustrate how effective communication and trust within teams can empower individuals to make...

In this episode, Craig and Andrew engage with Vijay Rajendran, a founder and entrepreneur, discussing the multifaceted challenges of leadership in startups. They explore the transition from being a 'Chief Everything Officer' to a more strategic role, emphasizing the importance of frameworks, resilience, and effective communication in navigating the startup landscape. Vijay shares insights...

In this episode, Andrew and Craig discuss the importance of problem solving in leadership, drawing from Craig's experiences in Afghanistan. They explore how leaders can creatively address unexpected challenges, the significance of collaboration and trust within teams, and the opportunities that arise from tackling problems head-on. The conversation emphasizes that effective leadership involves...

In this episode, Craig and Andrew discuss the challenges and changes that come with transitioning from a peer to a leader. They explore the importance of building trust, setting clear standards, and navigating difficult conversations. The conversation emphasizes the need for effective communication and the balance between authority and friendliness in leadership roles. They also highlight the inev...

In this episode, Craig and Andrew discuss the importance of empowering leadership through delegation, building trust within teams, and the balance between control and trust in leadership roles. They share personal experiences and insights on how effective delegation can enhance organizational success and the continuous journey of improvement in leadership skills. Empowering others through delegati...

In this episode, Craig and Andrew discuss the concept of After Action Reviews (AARs), emphasizing their importance in fostering a culture of learning and improvement within teams. They outline the structure and purpose of AARs, highlighting the need for open communication, accountability, and trust. The conversation covers the four key questions to guide AARs, the significance of documenting outco...

In this episode, Craig and Andrew discuss the significance of values in leadership and organizational culture. They explore how values guide actions, influence team dynamics, and impact customer loyalty. Through examples from companies like Chick-fil-A and Apple, they illustrate the importance of living values daily and the consequences of neglecting them. The conversation emphasizes the need for...

In this episode, Craig and Andrew discuss the essential elements of performance improvement coaching, focusing on how leaders can effectively navigate difficult conversations with their team members. They emphasize the importance of maintaining standards, setting clear expectations, and identifying root causes of performance issues. The conversation also covers the development of actionable plans...

In this podcast episode, Joseph Kopser shares his journey from a 20-year Army veteran to a successful entrepreneur with the founding of Ride Scout. He discusses the challenges of balancing military life with entrepreneurship, the importance of leadership, and the lessons learned from his experiences. The conversation also touches on the upcoming Leading to Win conference, aimed at bridging the gap...

In this episode of Command Post Cohort , Craig and Andrew dig into one of the most underrated leadership tools— the one-on-one meeting . Whether you call it a touchpoint, coaching session, or counseling, the title doesn’t matter as much as the intent: authentic conversations that build trust, uncover roadblocks, and develop your people. They walk through a practical, flexible one-on-one meeting te...

Andrew and Craig discuss the challenges and responsibilities of leadership, particularly in a military context. Andrew shares his experience of establishing a new unit within the Army, detailing the various obstacles he faced and the importance of taking charge. The discussion emphasizes the need for leaders to be proactive, build teams, and find solutions to problems, even when those tasks fall o...

In this conversation, Craig and Andrew discuss the multifaceted nature of leadership, emphasizing the importance of accepting responsibility, making decisions, and effectively communicating within a team. They explore the challenges new leaders face, the necessity of stepping up in crisis situations, and the critical role of problem-solving in leadership. The discussion highlights real-world examp...

This conversation explores the journey of a military veteran transitioning into the startup world, highlighting the challenges and lessons learned along the way. Johanna Wynne shares insights on the importance of taking risks, the clash of cultures between military and startup environments, and the unique challenges faced by women in the military. Through personal anecdotes and reflections, the di...