ON LEADING PODCAST • Episode #13 • January 3, 2024

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Episode #13

Dr. Jason Wingard

On Being Prepared for the Future

By Lori Brewer Collins

“This is a disruptive period in our world’s history, and people don’t like change. Change is not bad. It can allow opportunities for everyone. It doesn’t have to displace your current opportunities, your current future. So how do you get people to understand that change is good? How do you get them to make that change?”

These are some of the key questions Dr. Jason Wingard was reflecting on in the latest episode of Lori On Leadership. This globally renowned executive leader specializes in the future of learning and work and has deep experience in both the corporate and non-profit sectors. Dr. Wingard has spoken and published widely on the topic of strategy, learning, and leadership (The College Devaluation Crisis, The Great Skills Gap, Win the Leadership Game are some of his books). This year, he’s been on sabbatical, surrounding himself with some of the best minds in education and industry at Harvard. Together, these thought leaders, practitioners and researchers have been exploring how the world of learning should adapt to meet the needs of tomorrow’s world of work.

Jason is well qualified to talk about preparing for the future from this perspective. He currently is a Founding Partner and Chairman of The Education Board, Inc., a boutique management consulting firm specializing in corporate training, executive coaching, and corporate advisory services. From June 2021 to March 2023, he was the first Black President of Temple University, as well as their Professor of Management and Policy, Organizational, and Leadership Studies. He previously served as Dean of the School of Professional Studies and Professor of Human Capital Management at Columbia University. Prior to that, as Managing Director and Chief Learning Officer at Goldman Sachs, he was responsible for strategy and implementation of leadership development solutions for the firm’s partners and oversaw the acclaimed Pine Street Leadership Development Group and Goldman Sachs University.

Previously, he served as Vice Dean of the Wharton School, University of Pennsylvania, where he was the head of the Division of Executive Education and oversaw one of the world’s largest providers of leadership and management development. He also served as President & CEO of the ePals Foundation, and Senior Vice President of ePals, Inc. ePals, Inc. (now Cricket Media) is the world’s leading provider of interactive/collaborative learning products.

Prior to joining ePals, Dr. Wingard was Executive Director of the Stanford Educational Leadership Institute. He has also served in a variety of cross-functional executive and consulting roles for organizations including the Aspen Institute (senior fellow), the Vanguard Group (senior consultant), and Silicon Graphics, Inc. (program manager).

“Did I plan to be a college president? Did I plan to be a college dean? Did I plan to be on the top floor as an executive at Goldman Sachs? I didn’t plan any of that. I prepared myself with a foundation of knowledge and influence and networks. And when the opportunities presented themselves, I was ready to be able to take them.”

Key Takeaways

As a grandmother, I had a vested interest in hearing what he had to say about disruption in the global education sector. New technologies, new models, and new players means teaching and training tomorrow will undoubtedly be different than what it was in my time. He pointed out that the value proposition of the university degree, for instance, previously the most guaranteed route to prepare people for professional work, is no longer keeping up with the pace of change in society. Technological advancements are rapidly evolving the skills needed by organizations. If colleges and universities do not engage in responsive restructuring, more and more workplaces will bypass these traditional institutions entirely and, instead, use alternative sources of training that directly and quickly equip people with the dynamic competencies they need.

As a colleague and friend, I was also keen to learn about his own transformational journey as a leader. Here are a few nuggets I collected from him on making a difference during disruptive times:

  • Be intentional about the type of impact you want to have. Going into an organization, sometimes that impact will take a long time, sometimes a short time. Remain authentic and true to your values, no matter how long your stay.
  • Incrementally build a foundation at the grassroots level. Start local. Learn from what’s around you—then work the rings outward.
  • Be thoughtful and critical about the path forward. You have to have a strategy and a management plan. Be authentic as you begin to implement them. Be strong and fearless as you communicate bad news, uncomfortable course corrections, failures, or the end of a direct pursuit.
  • Be willing to make the future bumpier than the past. You are not here to please everyone and make sure their path is smooth. You are here to move the organization and the people in it forward along a path that needs to be optimally successful. As you develop more and more skill as a leader, you will get better at bringing people through very difficult moments.
  • Learn to not be friends with your leaders to the point where you cannot hold them accountable. Be willing and able to make those relationships uncomfortable. You are counting on them to have the right strategy, to make sure things stay on course, and to pivot and change direction when things go awry.
  • You will never get to the point where everybody is happy all the time. Leadership is not about being popular and having fans. It is about developing followership. Said another way, you can’t live by yourself in a glass house and expect to be an effective leader.
  • Develop your own professional “village” one person at a time. These are your people, individuals who already have trust and can establish trust for you inside the organization. Individuals who can act as your professional “friends”, your advocates and ambassadors.
  • Build your team of leaders to run the organization and build the culture. Think of yourself as a football coach with assistant coaches. Your assistant coaches build support for your vision. They can talk to players and fans alike, even talk to the owner of a process, and make sure things are implemented in the way you have instructed. They are the ones who build a culture in which everybody feels they are a leader. Then, together, you can navigate the turbulence of real change, disruption, and competitive fallout because everyone is aligned around the vision, mission, message, and the way things are done.

Dr. Jason Wingard

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