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Thank you to the 1,400 leaders who’ve generously done the 7 questions!
I hope reading

7 Questions with Brad Kershner

helps you in your leadership.



Jonno White

7 Questions with Brad Kershner

Name: Brad Kershner

Current title: Head of Early School

Current organisation: Carolina Friends School

Brad Kershner is a school leader and independent scholar, and the author of Understanding Educational Complexity: Integrating Practices and Perspectives for 21st Century Leadership.
His research, teaching, and writing cover a wide range of interdependent topics, including education, leadership, parenting, race, technology, metamodernism, integral theory, meditation, complexity, and developmental psychology. Some of his public lectures are available on YouTube (search: Dr. Brad Kershner). You can learn more about his work and access recordings of his guided meditations at

7 Questions with Brad Kershner

Which option best describes the religious affiliation of the organisation you currently work for or most recently worked for?

No religious affiliation

What type of organisation do you work for or support?

School (5-17 y/os)

1. What have you found most challenging as a leader in the education sector?

The biggest challenge in education is navigating the dynamics of social change. Schools are supposed to be preparing people for the future, but our social and technological world is changing so fast that it is impossible for educational organizations to stay ahead of the curve. The basic infrastructure and organizational logic of schooling is rooted in the industrial age. The primary challenge of education is to help educators, leaders, policy makers, and parents to understand the principles and contours of change in the 21st century, so that they may more skillfully support young people as they try to align their individual paths with the emergent needs of their world.

2. How do you structure your work days from waking up to going to sleep?

The interplay between structure and flexibility is key in any leadership role. I try to maintain structure around the basics - when and what I eat, getting outside every day, and finding time to be with my family and read at night.
Other than that, every day is a novel and creative flow of meetings, emails, and moments of presence with children, colleagues, and parents. The best and most important moment of every day is always this one.

3. What's the most recent significant leadership lesson you've learned?

I have been in discernment about my leadership path, and what the ideal role is for me to be in. I have been learning about vulnerability in the process of path refinement - learning to be open to new opportunities, while still being completely present and invested in my current role. Leading with integrity often means being fully committed and devoted to those you serve while also being open-minded about what the future holds. We're all growing and learning all the time, and the only constant is change. Holding this both/and perspective - both present to the fullness of responsibility and open to the call of the unknown - is crucial for leaders who are at their growing edge and willing to lean into new challenges in service of their own growth. Ultimately, what is best for one's individual path of growth and learning is also what is best for others.

4. What's one book that has had a profound impact on your leadership so far? Can you please briefly tell the story of how that book impacted your leadership?

There are so many books that have had a huge impact on me. Overall, the biggest insights I have gained have been from the field of developmental psychology, and two of the most important books I've read are: In Over Our Heads by Robert Kegan, and Integral Psychology by Ken Wilber.
Kegan has written several books that integrate adult developmental psychology and leadership. If we are going to meet the demands of the ever increasing complexity of the 21st century, we need to increase the complexity of our sense-making and relationships. Kegan offers deep insights about how most of us are 'in over our heads,' and not really able to meet the developmental demands of our professional and social responsibilities. This reality is especially important to understand in education, since the whole purpose of the educational endeavor is human development itself. Unfortunately, most of us have fallen into what Hanzi Freinacht calls 'developmental blindness,' where we don't see or understand how our individual and collective paths of human development shape the ways that we perceive, respond to, and shape our social world. This overarching problem was a big impetus for my own book, where I delve into the relevance and importance of adult development in the context of school leadership.

5. How do you find and keep great leaders in the education sector?

The principles that animate exceptional educational environments are applicable at every level, from kindergarten to college to leadership. We all want to work in environments that honor our individuality and enable us to exercise and develop our agency while engaged in meaningful and purposeful relationships with others (who are also empowered to cultivate their own professional sovereignty). The tensions between agency and communion should never go away; they should be the engine of individual and collective growth. Leaders need to be trusted to build trust; they need to be empowered to empower others; and they need to be supported so they can model their own ongoing learning, while encouraging others to do the same. The enemies of leadership and collective thriving are standardization, conformity, group-think, and fear. Avoid these, listen closely to what people are actually experiencing at every level of organization, and leaders will be drawn to facilitate the emergence of the collective that empowers their own fulfillment and purpose.

6. What's most important as a leader in the education sector for developing a culture of wellbeing in your staff and students?

As noted above, the same principles apply at every level. Leaders can't thrive unless there is a culture of wellbeing for everyone, and vice versa. The primary intention of leadership must be to empower others in service of their own growth. If individuals are actually growing and maturing in their work, their inevitable interdependence with others will ensure a collective wellbeing. Modeling wellbeing and supporting staff to enact personal and professional wellbeing will enable and empower staff to model for and support students. But if you don't embody wellbeing, consistently and authentically, then there is no way for these positive feedback loops to get grounded.
Also, an obvious thing to avoid and guard against is the corrosive influence of external mandates. As much as possible, schools (like all organizations) need the autonomy and empowerment to develop their own goals and processes, in alignment with their self-determined values. The failure to honor this basic cultural/psychological imperative is one of the main contributors to turnover, burnout, and lack of wellbeing in schools.

7. What is one meaningful story that comes to mind from your time as a leader in the education sector so far?

So many. Every relationship is a story, and a series of stories. Two come to mind with the same theme: joy.
As a K-8 Principal in Boston, at the end of the year we had a Field Day, filled with games and sporting events. After the year was over, I realized that we should have done an event like that at the start of the year, and maybe periodically! Being able to engage staff and students in pure play and fun is priceless - and being able to show that I was the best basketball player at the school didn't hurt in the effort to establish street cred :-)
As Director of another school, we instituted Friday Finales - end of the week celebrations every Friday afternoon, with school sing-a-longs that included parents. It was a joyful and awesome way to end each week, and we did it all year. These things are important. All leaders should look for opportunities to create new traditions and rituals for collective joy.

We're looking at doing a limited, online 30 minute leadership masterclass in the next couple of months. What topic/s would you find most valuable from a leadership masterclass?

What do you do to bring joy to yourself and others in your work?

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