July 24, 2025
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An early leadership Question.
Do you remember your first leadership position?
Yesterday, I celebrated my 75th year—a milestone that naturally brings with it a moment of reflection and gratitude for the people and events that have shaped my leadership journey. As I look back, I’m struck by how much my approach to leadership has changed with the times.
One memory stands out: early in my career in a suburban high school, rules and consistency were king. Yet on the very first day, I faced a challenge—a pregnant student assigned a last-period lunch pleaded for an earlier one due to her medical needs. Helping her meant bending the rules, and indeed, my supervisor dubbed me a “bleeding heart” for the remainder of my time at that school district. Despite the ribbing, that experience taught me something essential: authentic leadership often isn’t about choosing between enforcing rules or meeting human needs, but learning to hold them in tension. Many years later, I was recognized in my first retirement for having the ability to “make it work”—a trait I now see as the essence of paradoxical leadership.
This Thursday’s leadership insight is the first of a two-part series on paradoxical leadership. Paradoxes that all leaders must come to grips with will be shared, drawing heavily on the work of Dr. Elmore, John Maxwell, and other leadership experts. This week, we consider what a paradox is, what paradoxical leadership entails, and six benefits of paradoxical leadership. Part II will consider primary paradoxes in today’s leadership context.
“A paradox is simply a contradictory proposition that, when investigated, may prove to be well-founded and true.”
Dr Tim Elmore
What is a Paradox?
A paradox is a statement or situation that appears self-contradictory or absurd, yet holds a deeper truth upon closer scrutiny. Leadership history is filled with paradoxical acts. I crewed for my Uncle Herb, a seasoned sailor on the Great Lakes. He frequently practiced tacking in a zig-zag pattern to catch the most wind and reach the finish line faster than sailing straight. The wisdom lies in embracing a “both/and” mindset rather than falling into “either/or” thinking.
In leadership, a paradox means embodying two seemingly opposing qualities at the same time. John Maxwell and Tim Elmore both argue that great leaders don’t view these tensions as problems to be solved, but rather as realities to be understood and managed along a continuum.
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Why Paradoxical Leadership Matters
In today’s rapidly changing world, effective leaders must be agile enough to handle constant change while remaining firmly grounded in their core values. Thomas Jefferson offered timeless wisdom:
“In matters of style, swim with the current; in matters of principle, stand like a rock.”
Thomas Jefferson
Dr. Tim Elmore, author of The Eight Paradoxes of Great Leadership, and Dr. John C. Maxwell, in The 21 Irrefutable Laws of Leadership, emphasize that leading today often means holding seemingly opposite qualities—being both tough and tender, adaptable yet consistent, and confident yet humble. This ability is not only helpful but also essential for nurturing thriving teams and navigating complex organizational landscapes.
Six Benefits of Paradoxical Leadership
Here are six reasons why embracing paradox makes for better leadership in today’s world:
Fosters Adaptability: Leaders gain the flexibility to respond to rapid changes while maintaining core purpose.
Builds Trust: balancing consistency with empathy strengthens credibility and rapport with teams.
Encourages Innovation: Welcoming seeming contradictions sparks creativity and new solutions.
Enhances Problem-Solving: Navigating tensions enhances decision-making in complex and uncertain situations.
Drives Engagement: Integrating structure with freedom appeals to diverse teams and boosts motivation.
Develops Resilience: Managing paradox prepares organizations to bounce back from setbacks and thrive through adversity.
“Uncommon leaders stand out because they can juggle seemingly contradictory traits to lead such people.”
Dr. Tim Elmore
Conclusion: Embrace the “Both/And”
We lead in times of competing pressures—rapid change, rising expectations, and shifting values. The leaders who stand out are those who learn to step forward and back, enforce rules and extend grace, lead boldly, and listen deeply. This paradoxical approach isn’t always straightforward, but it may be precisely what the world needs most right now.
Next Thursday, we’ll explore the specific paradoxes leaders commonly face today and build practical tools to “make it work” for those we serve.
The leadership question for you then is
- How have you managed a paradox in your own leadership journey?
I’d love to hear your thoughts and stories.