Episodios

  • 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 m
  • 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 m
  • 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 m
  • 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 m
  • Mastering the Art of Planning Episode 11
    May 14 2025

    In this conversation, Andrew and Craig discuss the critical role of planning in leadership and organizational success. They emphasize the importance of both short-term and long-term planning, the value of backwards planning, and the need for proactive strategies to mitigate risks. The discussion also highlights the significance of communication and team empowerment in the planning process, as well as the necessity for leaders to remain agile and adaptable. They introduce the one-thirds two-thirds rule as a framework for effective time management in planning tasks. Ultimately, the conversation underscores that planning is an investment that yields significant returns in execution and team performance.

    www.outsiders-group.com

    www.commandpostcohort.com


    Takeaways

    Planning is essential for effective leadership.

    Both short-term and long-term planning are necessary.

    Backwards planning helps in achieving long-term goals.

    Proactive planning reduces the likelihood of conflicts.

    Effective communication is key to successful planning.

    Agility in leadership allows for better adaptation to changes.

    Incremental planning can lead to significant improvements.

    The one-thirds two-thirds rule optimizes planning time.

    Building trust through open communication enhances team performance.

    Planning is an investment that pays off in execution.



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    38 m
  • Falling Off the Mountain: A Leadership Lesson Season 1 Episode 10
    May 7 2025

    In this episode, Craig shares a personal story from Ranger School, highlighting the challenges faced during the rigorous training. He recounts a specific incident during the Mountain Phase where he fell off a mountain due to a communication breakdown regarding safety instructions. The conversation explores the importance of clear communication, the impact of individual actions on team dynamics, and the lessons learned from both leadership and followership perspectives. The discussion emphasizes that even small missteps can have significant consequences in high-stress environments, and the importance of asking for clarification to prevent misunderstandings.



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    26 m
  • The Circular Nature of Effective Training, Episode 9
    Apr 30 2025

    In this episode, Craig and Andrew discuss the critical aspects of training management, emphasizing its circular nature, the importance of progressive training, and the need for continuous improvement in leadership. They explore how to identify training needs, implement effective training systems, and the significance of rehearsals and after action reviews in enhancing performance and preventing incidents. The conversation highlights that training is an ongoing journey for both employees and leaders, essential for organizational success.



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    34 m
  • Embracing Change in Organizations
    Apr 23 2025

    This conversation explores the dynamics of change within organizations, emphasizing the importance of adaptability, communication, and trust in leadership. The speakers discuss how technology influences change, the military's perspective on accepting change, and the necessity of engaging employees during transitions. They highlight real-world examples and the significance of navigating difficult conversations to foster a culture that embraces change.

    #leadership #leaderdevelopment #changemanagement #commandpostcohort #outsidersgroup


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    37 m
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