5 Paradoxes of Effective Leadership

Gloria Feldt
5 min readApr 18, 2023

Issue 226— April 17, 2023

I’m having a blast leading the new mastermind series, “Intentioning: Transform Your Dreams to Reality with the Power of Intention” live online. I love the real-time interaction, yet busy women from all over the world can participate and have the flexibility to catch up asynchronously while being part of a supportive community of women.

“We are in a season of disruption; we are in a season of rebirth. The two have much in common.”

I wrote that in the introduction to my book Intentioning during the apex of the pandemic. I wanted to illustrate the power of such a paradox to open minds so that we can solve problems and reshape our world in ways that would never have been accepted during more “normal” times. Stasis doesn’t breed nearly as much innovation as disruption does.

That led to a deep discussion of how paradox is an inherent aspect of leadership. Leaders typically live in paradox, and have to become comfortable doing so. Solutions to complex problems are rarely cut and dried. Often there are competing forces that when analyzed with a visionary mind can be leveraged into creative, novel solutions.

Getting ready for the Intentioning Mastermind Series.

The dictionary definition of paradox: a statement or proposition that seems self-contradictory or absurd but in reality expresses a possible truth.

Because many of the women joined the Mastermind series to gain clarity about their highest intentions for their lives and their careers, I told them they’ll need to get comfortable with paradox.

Very little is absolute, especially as we ascend into upper levels of leadership. The leader who can not only thrive in paradox but can use the creative problem solving that paradox forces you to have is the leader who can excel at being her authentic self.

Most of the time collectively and as individuals, we are in one or both disruption and rebirth. At times like these, it’s good to remember there are always times like these and to embrace the paradox.

5 Paradoxes of Leadership

  1. People hunger both to be led and to lead. This is true of almost everyone, because leadership is a tremendous responsibility and those who accept it with attention to the ethical dimensions as well as the business goals of their organization can’t help but want to learn continuously from other leaders, and to lean on their wisdom.
  2. We want leaders to articulate a compelling vision and yet to feel we have participated in the creation of that vision.
  3. We generally want to be told what is expected of us, to have boundaries or a clear structure, and to have freedom within those boundaries to decide for ourselves the best course of action in our work. We neither want full autonomy nor fully rigid structure. Boundaries that are malleable are paradoxically the most effective so people have freedom to achieve goals in ways they believe are most effective.
  4. We need to get personal satisfaction, yet in reality we are most satisfied when we are working for something larger than ourselves.
  5. Those who will be most successful as leaders or at being tapped for leadership roles are inevitably those who embrace chaos and ambiguity and turn them into opportunities.

In paradox, in disruption, is where the innovation lies, where problem solving occurs most fruitfully. It’s where you grow and help others grow. It is — paradoxically — where you can ultimately find clarity.

The insider-outsider paradox of female leaders has become a superpower.

Psychologists Dick Farson and Carl Rogers worked together to develop theories of social psychology and active listening.

Women and other underrepresented groups have an opportunity to embrace paradox uniquely to be successful leaders.

In her book When Women Lead: What They Achieve, Why They Succeed, and How We Can Learn from Them, Julia Boorstin explains how when women become corporate leaders, they paradoxically become both insiders who are now part of the system and yet remain outsiders because they have not had the privilege of power when they come into their more powerful roles. They can see things differently than the men who have historically been the leaders. That in turn leads to greater empathy, problem solving, and innovation.

Boorstin gives the example of financial executive Sallie Krawcheck, founder of the women-focused investment advisory and platform Ellevest. Before launching Ellevest in 2016, Krawcheck had been a top executive at a series of major financial institutions, including Smith Barney, Citi, and Merrill Lynch. She was often at odds with her bosses about the needs of female investors, but her experience being an outsider/insider ultimately gave her the ability to understand gender differences in investment decisions and in the earning curve of women compared to men. She saw an untapped market of women who had the wherewithal to invest, including opportunities to start investing at lower levels, but were not being served in a way that resonated with them, whereas the mostly male leaders could not envision a different market paradigm.

As one of my mentors, the late Richard Farson, author of Management of the Absurd: Paradoxes in Leadership, was fond of saying, “Nothing is as invisible as the obvious.”

So if you are aiming to be an effective leader, consider how understanding these paradoxes can help you achieve your highest intentions, and perhaps paradoxically, listen attentively to your own inner counsel.

GLORIA FELDT is the Cofounder and President of Take The Lead, a motivational speaker and expert women’s leadership developer for companies that want to build gender balance, and a bestselling author of five books, most recently Intentioning: Sex, Power, Pandemics, and How Women Will Take The Lead for (Everyone’s) Good. Honored as Forbes 50 Over 50 2022, and Former President of Planned Parenthood Federation of America, she is a frequent media commentator. Learn more at www.gloriafeldt.com and www.taketheleadwomen.com. Tweet Gloria Feldt.

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Gloria Feldt

Gloria Feldt is a New York Times bestselling author and co-founder and president of Take The Lead, a nonprofit women’s leadership organization.