Episodes

  • Taking Charge: The Essence of Leadership
    Jul 9 2025

    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 examples from the fire department and other leadership contexts, providing insights into the dynamics of leading a team and the courage required to navigate various challenges.

    Takeaways

    • Leadership requires accepting responsibility for decisions.
    • New leaders often struggle with stepping into their roles.
    • Effective communication is crucial in leadership.
    • Leaders must solve problems proactively.
    • It's important to view oneself as a leader.
    • Courage is necessary for making tough decisions.
    • Leaders should come with solutions, not just problems.
    • Team dynamics play a significant role in leadership success.
    • Understanding the impact of decisions on the team is vital.
    • Leadership is a continuous learning journey.

    www.commanpostcohort.com

    www.outsiders-group.com


    #leadership #leader #communication #purpose #standards #trust

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    30 mins
  • The Foundations of Our Leadership Development
    Jun 25 2025

    In this conversation, Craig and Andrew reflect on their leadership journeys, particularly focusing on their experiences in ROTC and how it shaped their leadership styles. They discuss the impact of high standards, accountability, and authentic leadership in building a strong cohort culture. The conversation emphasizes the importance of trust and teamwork in leadership development, drawing from personal anecdotes and lessons learned throughout their military training.


    Takeaways

    • Leadership is shaped by both nature and nurture.
    • High standards were a key component of their training.
    • Building a culture of accountability was essential.
    • Authentic leadership fosters trust and connection.
    • Team dynamics play a crucial role in leadership effectiveness.
    • Repetition and practice are vital for skill mastery.
    • Leaders are responsible for their team's performance.
    • Feedback and personal interactions enhance learning.
    • Leadership lessons learned early in life have lasting impacts.

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    32 mins
  • From Military to COO: A Leadership Journey
    Jun 18 2025

    In this episode, Andrew and Craig engage with Bill Helmsing, a former military officer turned COO, discussing his journey from the Army to leading startups. They explore the challenges of transitioning leadership styles, the importance of building trust within teams, and the necessity of creating a culture of innovation and accountability. Bill shares insights on establishing organizational values, the significance of feedback, and the process of developing future leaders. The conversation emphasizes the importance of resilience, communication, and the role of strengths in effective leadership.


    Takeaways

    Leadership is a continuous journey that requires constant learning.

    Building trust in teams is essential for effective leadership.

    Creating a culture of innovation involves psychological safety.

    Values must be enforced consistently to be effective.

    Feedback is crucial for individual and organizational growth.

    Playing to people's strengths can enhance team performance.

    Transitioning from military to civilian leadership requires adapting styles.

    Establishing clear expectations is vital for accountability.

    Difficult conversations are part of leadership responsibilities.

    Developing future leaders starts with having meaningful conversations.





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    44 mins
  • Navigating Leadership Risks
    Jun 11 2025

    In this episode, Craig and Andrew discuss the multifaceted nature of risk in leadership, particularly in military and business contexts. They explore how complacency can lead to unforeseen dangers, the importance of communication in mitigating risks, and the necessity of having processes in place to manage both internal and external risks. Through real-life stories from Afghanistan, they highlight the lessons learned and the complexities of decision-making under pressure, emphasizing that leaders must navigate ambiguity while prioritizing safety and operational effectiveness.


    Takeaways

    Risk is not just physical; it encompasses financial and operational aspects.

    Complacency can lead to overlooking significant risks.

    Effective communication is crucial in managing risks during operations.

    Leaders must assess both internal and external risks.

    Processes and frameworks are essential for risk management.

    Learning from past experiences can improve future decision-making.

    Leaders should prioritize safety without losing sight of mission objectives.

    Assuming some risk is sometimes necessary for effective leadership.

    Ambiguity is a part of leadership; decisions are rarely clear-cut.

    Continuous improvement through after-action reviews is vital.



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    29 mins
  • Mastering Agility in Leadership episode 14
    Jun 4 2025

    Craig and Andrew discuss the importance of agility in leadership, particularly in the face of unexpected changes. They share insights from military experiences, emphasizing the need for trust, communication, and a growth mindset within teams to navigate challenges effectively. The conversation highlights how leaders can foster resilience and adaptability in their teams, ensuring they can respond to new missions and environments with confidence.

    Takeaways

    • Agility is a crucial skill for leaders in changing environments.
    • Building trust within a team is essential for effective adaptation.
    • Unexpected changes can arise at any time, requiring quick responses.
    • Communication is key to navigating new challenges as a team.
    • A growth mindset allows teams to embrace change and learn from it.
    • Leaders should maintain composure to instill confidence in their teams.
    • Resilience in teams is often a reflection of their leader's attitude.
    • Effective planning is necessary for executing sudden mission changes.
    • Cross-training team members enhances adaptability during transitions.
    • Trust and cohesion enable teams to operate effectively in unfamiliar situations.

    www.commandpostcohort.com

    www.outsiders-group.com


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    22 mins
  • Monthly Military Connected Mentor Meetup: Live podcast with Jim Orbock | May 17, 2025
    May 28 2025

    This special episode was recorded live at The Capital Factory in Austin, Texas, as part of the Monthly Military Mentor Meetup. Andrew was joined by cohost Jeremy from Startup Anthology and guest Jim Orbock.


    This conversation explores the journey of transitioning from military leadership to entrepreneurship, emphasizing the importance of trust, mentorship, and maintaining focus in a startup environment. The speakers share personal experiences and lessons learned, highlighting the challenges and rewards of leading teams in both military and business contexts. This conversation revolves around the themes of networking, startup challenges, organizational structure, intentional hiring, mentorship, community building, and the importance of storytelling in leadership. Participants share their experiences, and insights, creating a rich dialogue focused on fostering innovation and building teams.




    Takeaways

    Leadership lessons are crucial for startup culture.

    Transitioning from military to entrepreneurship requires adaptation.

    Narrowing your vision is essential for success.

    Mentorship and reading are key to personal growth.

    Building trust within teams fosters loyalty and performance.

    Servant leadership is vital for employee engagement.

    Psychological safety encourages innovation and risk-taking.

    Understanding different perspectives enhances decision-making.

    Effective leaders delegate and empower their teams.

    Maintaining company culture is challenging as businesses grow.

    Networking is essential for building connections and opportunities.

    Scaling a startup requires clear organizational structure and defined roles.

    Intentional hiring can solve specific problems within a team.

    Mentorship plays a crucial role in personal and professional growth.

    Community building is vital for veterans transitioning to civilian life.

    Storytelling enhances leadership and fosters a sense of belonging.

    Understanding different perspectives can improve team dynamics.

    Feedback on innovative ideas is crucial for validation and growth.

    Defining roles and responsibilities can enhance efficiency in teams.





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    28 mins
  • The Six Steps to Effective Decision Making, Episode 12
    May 21 2025

    In this episode, Craig and Andrew discuss the importance of decision making in leadership. They present a structured framework consisting of six steps to enhance decision-making processes. The conversation covers defining the decision, gathering relevant information, evaluating options and risks, making and communicating the decision, implementing and monitoring the decision, and gathering feedback for continuous improvement. The hosts emphasize the need for clear communication and the importance of learning from past decisions to foster a culture of improvement within organizations.


    TakeawaysDecision making is crucial for leaders.A structured framework aids in effective decision making.

    Clearly define the problem before seeking solutions.

    Gather relevant information from various sources.

    Evaluate options and risks thoroughly before deciding.

    Communicate decisions clearly to the team.

    Implementation requires monitoring and the ability to adjust.

    Feedback loops are essential for continuous improvement.

    Knowledge management helps retain lessons learned.

    Decisions can range from simple to complex, requiring different approaches.




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    37 mins