July 31, 2025

As leaders, our most significant opportunity lies not in choosing between strengths but in holding healthy tensions and unleashing the best in ourselves and our teams. Paradoxical leadership isn’t only insightful, it’s essential for leading in the context of the times in which we live.

In today’s world of relentless change and mounting complexity, effective leadership demands more than proficiency in classic skills; times call for the ability to embrace and leverage paradoxes. This edition of Thursday’s Leadership Insight delves deeper into what paradoxical leadership truly means, why it’s essential, and how you can cultivate it for yourself and those you lead.

What is Paradoxical Leadership?

A paradox is a situation or concept that appears self-contradictory yet reveals a more profound truth upon further examination. In leadership, paradoxes aren’t problems to solve or dilemmas to avoid; they are viewed as tensions to manage and leverage. As Dr. Tim Elmore notes, “A paradox is simply a contradictory proposition that, when investigated, may prove to be well-founded and true… for leaders, it’s so complex to lead today that part of the answer is to lead with a ‘both/and’ rather than an ‘either/or’ mindset—embrace paradoxes.”

Uncommon leaders thrive because they juggle seemingly contradictory traits to guide, empower, and inspire.

The Ten Leadership Paradoxes of Uncommon Leadership

Let’s unpack the ten core paradoxes that set uncommon leaders apart, with insights and examples from leadership experts:

1. Serve First, Then Lead

Robert Greenleaf described the true leader as a “servant first.” Uncommon leaders choose service over self-interest as their foundation. Jim Rohn captured the paradox beautifully: “Be strong, but not rude; be kind, but not weak; be bold, but not a bully…” Leaders serve first, but do not relinquish their responsibility to lead. This is especially true when working with a multi-generational workforce that employs a reverse mentoring model, pairing younger workers with older workers to learn from each other’s skill sets and perspectives.

2. Balance Confidence and Humility

Great leaders, such as Abraham Lincoln, strike a balance between unwavering conviction and genuine humility. He built a team of advisors who were bitter political foes, from whom he learned. Confidence keeps you on course; humility ensures you remain open to growth and learning.

3. Leverage Both Vision and Blind Spots

Vision anchors direction, but recognizing blind spots stimulates collaboration and practical problem-solving. Walt Disney dreamed of EPCOT, stretching the imagination while inviting diverse expertise to bridge the gaps.

4. Embrace Both Visibility and Invisibility

Step into the spotlight when needed (as Adam Silver did during the NBA COVID-19 crisis), but also know when to withdraw and let others rise. As Sheryl Sandberg reminds us, “Leadership is about making others better as a result of your presence—and making sure that impact lasts in your absence”.

5. Stubborn Yet Open-Minded

Stay dogged about your vision (“the what”), but flexible about “the how.” Coach K (Mike Krzyzewski) and Nick Saban exemplified how halftime adjustments—anchored in core principles—create championship cultures.

6. Deeply Personal and Inherently Collective

Connect with individuals, but always rally around a shared vision. John Maxwell states, “People don’t care how much you know until they know how much you care.” Nelson Mandela led by forging genuine bonds and uniting South Africa under a common cause.

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7. Teacher and Student

Model lifelong learning. Mark Miller observes, “The best leaders are lifelong learners.” The willingness to learn from all, regardless of status, builds engagement and prepares future leaders. Being a learner and teacher provides leaders with the opportunity to look up, down, and all around, and leverage the skills and perspectives of a multi-generational workforce.

8. High standards and gracious forgiveness, coupled with high support

Pursue excellence, but temper it with mercy and understanding. Tim Elmore says, “They don’t lower their standards; they forgive those striving to improve.” Steve Jobs demanded excellence, yet fostered innovation by allowing the freedom to fail. David Yaeger, in 10 to 25, refers to this as a Mentor’s Mindset.

9. Timely and Timeless

Navigate current trends while securing the future and holding fast to the core values (Values, Purpose, Motivation, and Mindset. While being agile in seeking ways to navigate the process, John Maxwell urges leaders to see beyond the moment, holding fast to enduring values. The 5-star sit-down restaurant that pivoted to delivery and pickup during the COVID-19 pandemic preserved jobs and its mission, adapting its methods but maintaining its core purpose.

10. Develop Hard and Soft Skills

Today’s leaders can’t master everything, so they partner, empower, and build both technological and relational competencies. The authors of The Journey of Leadership highlight the rise of “humancentric” leadership, blending knowledge with emotional intelligence for sustainable success.

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BONUS 11. Paradox is a mentor and mentee

Today’s exceptional leaders have a mindset to be mentors and grow new leaders, and are mentored by what Maxwell Leadership CEO Mark Cole refers to as an inner circle, including John Maxwell, who speaks into and supports their leadership.

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Five Key Advantages of Embracing Paradox

Adaptability: Leaders who embody both/and thinking respond more effectively to diverse and changing circumstances.
Creativity: Multiple perspectives fuel innovation and creative problem-solving.
Constructive Response: Paradoxical leaders address challenges with openness and collaboration.
Development of Self and Others: A learning mindset and cultural safety for all, including leaders, empower growth and leader development.
Resilience: Practicing both/and thinking helps leaders and organizations thrive amidst uncertainty.

Six Ways to Learn to Embrace Paradox in Your Leadership Practice.

1. Cultivate a Both/And Mindset: Change how you view problems from challenges or threats to tensions to manage, not either/or trade-offs. Reframe challenges to find integrative solutions.
2. Balance Opposing Traits: Practice embodying both sides of each paradox—teach and learn, hold standards and forgive, speak up and listen, pause to reflect and ask powerful, curious questions..
3. Surface and Manage Tensions: Don’t shy away from conflict—name it and engage it to spark connection and learning.
4. Cultivate Cognitive Complexity: Learn to appreciate nuance and build bridges between competing leadership demands.
5. Model Adaptability: Shift approaches as circumstances change, while staying grounded in values.
6. Learn from Exemplary Leaders: Seek mentors, study biographies, and continually reflect on your own practice.

Daniel Sih writes, “The beauty of paradox—it’s not about choosing either/or, but embracing both/and. By approaching life’s challenges through this lens, we open ourselves to new ways of thinking, unlocking fresh insights rather than being locked into polarities.”

Two leadership questions.

What practices will you apply to use paradoxes to enhance your leadership practice?

How will you choose to incorporate these paradoxes into your leadership practice?