E102 – Preparing for Leadership featuring Craig P. Anderson

Trench Leadership: A Podcast From the Front

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I’d like to begin this episode by acknowledging the land that I am learning and living on is the traditional un-ceded, un-surrendered territory of the Anishinaabeg Algonquin People.

Craig P. Anderson's journey from an aspiring high school teacher to leading a national sales team at JPMorgan Chase is a testament to the unpredictable paths leadership can take. His story of becoming an "accidental leader" reveals the complexity of emotions faced when stepping into leadership roles, highlighting the crucial balance between excitement and fear. Craig's insights emphasize the importance of recognizing leadership potential and preparing for the challenges that lie ahead. Through personal anecdotes, we explore the significance of learning from mistakes and the role of coaching in fast-tracking leadership capabilities.
Many organizations underestimate the value of sustained mentorship, viewing it as an expense rather than a long-term investment in effective leadership. We delve into strategies that can bridge this gap, advocating for ongoing support and structured programs to nurture the skills of young leaders, ensuring they are well-equipped to navigate the complexities of their roles.
Through compelling examples, including a cautionary tale from Canadian military history, we underscore the necessity for clarity and precision in leadership instructions. Emerging leaders are encouraged to cultivate self-awareness and understand team dynamics, all while maintaining a clear focus on outcomes and priorities. By fostering intentional leadership and continuous learning, we aim to inspire leaders to pursue their roles with the right motivations, driving both personal and professional growth.

In this episode we'll discuss the following topics:
• Challenges that new leaders encounter in their roles
• The gap in formal leadership training provided by organizations
• The importance of investing in leadership development
• Practical strategies for emerging leaders to build confidence
• The necessity of mentorship and coaching in leadership
• Understanding individual team members and tailoring support
• Setting clear goals and expectations to improve team alignment
• Continuous learning as a cornerstone of effective leadership

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Trench Leadership: A Podcast From the Front is humbled to have been named #5 in the Top 20 for Best Canadian Leadership-themed podcasts for 2025.

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Chapters

1. E102 – Preparing for Leadership featuring Craig P. Anderson (00:00:00)

2. Leadership Challenges for Emerging Leaders (00:00:07)

3. Effective Leadership Development Strategies (00:08:47)

4. Navigating Leadership Challenges for Emerging Leaders (00:14:41)

5. Clarifying Expectations for Emerging Leaders (00:23:54)

6. Navigating Challenges for Emerging Leaders (00:36:00)