The Resilient Leaders Podcast with J.R. Briggs Ep 350: The 21 Common Challenges Leaders Face
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Sep 2, 2026 Leadership rarely comes with a clear path. This conversation explores 21 recurring challenges, from decision fatigue, board tension, and financial strain to team misalignment, conflict, loneliness, and uncertainty. It also examines accountability, founder dependence, developing new leaders, work-life balance, self-leadership, transitions, emotional intelligence, fear, and imposter syndrome.
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Twenty-One Challenges Recur Across Leadership Contexts
- Leadership challenges recur across contexts, even though every organization has unique complexities.
- J.R. Briggs identified 21 patterns that frequently emerge among the leaders Kairos Partnerships serves.
Recognize Decision Fatigue Before It Becomes Unsustainable
- Reduce decision fatigue by recognizing when the volume of daily choices has become unsustainable.
- Also examine board dynamics and financial shortfalls as distinct pressures requiring deliberate leadership attention.
Test Whether Your Organization Can Survive You
- Address unhealthy culture, team misalignment, founder dependence, weak communication, and relational conflict directly.
- Ask whether the organization can survive the founder leaving tomorrow, the episode's “bread truck test.”