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 template that leaders can use to support team members, track progress, provide feedback, and align goals. Craig shares lessons from his Army experience, and Andrew tells a story of how one conversation helped unlock a soldier’s potential—leading to the best retention rate in U.S. Army Europe.

If you’re a new leader looking for a structure—or a seasoned one trying to reset expectations—this episode offers real talk, real tools, and real stories to help you lead better today.

📎 Download the free one-on-one template at commandpostcohort.com
📺 Watch this episode on YouTube for the screen-shared walkthrough
💬 Connect with us and suggest topics at commandpostcohort.com

Enhance Your Leadership Skills with Proven Strategies

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 outside their traditional roles. The conversation highlights the significance of trust, adaptability, and decision-making in effective leadership.

Takeaways

• Leadership requires taking charge and being proactive.
• Building a team of teams is essential for success.
• Leaders must navigate unfamiliar responsibilities effectively.
• Overcoming obstacles often involves creative problem-solving.
• Trust in your abilities and the support of your team.
• Assuming risk can lead to faster decision-making.
• Communication is key in coordinating efforts across teams.
• Leaders should come with solutions, not just problems.
• Adaptability is crucial in dynamic environments.
• Leadership and change are inherently linked.

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leadership, military, team building, problem solving, responsibility, decision making, trust, organizational structure, communication, adaptability

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.

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

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 discussion emphasizes the significance of mentorship, innovation, and the need for trust and delegation in leadership roles.

Recorded live at the Military-Connected Mentorship Meetup in Austin Texas, with special thanks to The Capital Factory,@TexasVeteranChambersCoalition‬ , ‪@IVMFBunkerLabs‬, ‪@IVMFSyracuseU‬, ‪@combinedarmsus‬, and Dress for Success Austin Takeaways

• Life is short, and we should seize opportunities now.
• Failure is an essential ingredient to success.
• Trusting others is crucial for scaling a business.
• The military and startup cultures can clash significantly.
• Women veterans often face unique challenges in visibility and advocacy.
• It's important to listen to your inner voice and follow your path.
• Delegation can be difficult but is necessary for growth.
• Being part of a supportive community is vital for women in the military.
• Taking risks can lead to valuable learning experiences.
• Navigating change requires adaptability and open-mindedness.

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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.

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.

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.

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.

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