In Session Reflections

It turns out you can learn a lot in five minutes.

Over the past year, close to every week we have published a new In Session video from the Aspen Institute, a short focused conversation featuring practical wisdom from across the Institute’s global community. Every episode goes up on YouTube, with shorter cutdowns for LinkedIn and Instagram.

I had the privilege of being in the room for every interview. That meant sitting across from leaders and builders at the top of their fields and asking them to talk honestly about the moments that shaped them. Some of the videos I come back to regularly include:

• Simon Godwin, the artistic director of the Shakespeare Theatre Company and the 2023/24 Harman Eisner Artist in Residence for the Aspen Institute Arts Program, making the case for being more spontaneous. “For a long time I thought the role of a leader was to be a serious, thoughtful, rather sober figure,” he says. “But as I have directed more and more plays, worked with more and more extraordinary actors, I have realized the opposite is true. Actually, my job is to bring playfulness every day into the spaces that I lead.”
• Andy Cunningham, the Aspen Institute trustee and Silicon Valley marketing and communications leader, laying out how culture drives behavior and how the best leaders give people the freedom to execute. “You have to give people the freedom to execute things the way that they think they should be executed and not micromanage them,” she says. “You cannot get a bunch of people to do things for you if you are micromanaging them. So you give them the goal, you set the expectation, and then you let them do it.”
• Alex Azar, former United States Secretary of Health and Human Services and Aspen Institute board trustee, sharing the critical lessons he learned while overseeing Operation Warp Speed, an ambitious collaboration between the federal government and the private sector that aimed to accelerate the development of a COVID vaccine. According to him, “A team gains confidence by knowing that you have delegated to them, that they have the authority to make decisions, to drive forward, to not look over their shoulders all the time.”
• Carly Zakin, the cofounder and co CEO of theSkimm and Henry Crown Fellow, sharing advice for entrepreneurs, including embracing the unknown, building a support network, and refreshing it constantly. “There is a reason people say it can feel lonely at the top,” she says. “It often does. But that does not mean you have to be alone. It is essential to build a network of trusted personal advisors, your own board that you can turn to and say, ‘I need help,’ or ‘I am not sure what to do,’ or simply, ‘Can I talk this through with you?’ The key is recognizing that this circle of advisors should evolve as you grow.”
• Dar Vanderbeck, vice president of the Aspen Global Leadership Network, on the importance of being first in the water. “There is some inherent value to putting up your hand and going first, and going first not just out of bravado but by being able to acknowledge that this is scary and still we are going to learn together,” Dar says. “So let us get going. I think that is such an important idea for people in the beginning of their leadership journeys.”
• Yuliya Tychkivska, executive director of Aspen Institute Kyiv, reflecting on lessons she has learned during her life and from the war in Ukraine. “Leadership is really different from management,” says Yuliya. “It is not just about managing people and making things happen. It is about caring about your people. It is about inspiring. It is about giving hope to your team and leading this community of people who are part of your community.”
• Corby Kummer, executive director of Food and Society at the Aspen Institute, reflecting on ingredients of successful leadership like turning self doubt into strength and using dialogue as an essential tool. “Everybody has doubts about kind of everything they do, but you have got to keep going,” he says. “It is that simple. Even if something fails once, fails twice, fails three times, you keep going with it.”

But those are just a few of so many.

The In Session videos span business, policy, economic mobility, the arts, academia, social impact, and more. What stood out most for me was not the range of sectors but the common threads of Aspen leaders: integrity, purpose, resilience, curiosity, and the courage to take smart risks.

As a content creator, producing In Session has been a dream project. It has also been a welcome crash course in leadership. These are real stories and real lessons distilled into something you can take with you in under five minutes

More than anything, this series has shown me how deep insight and experience runs within the Aspen Institute network, far beyond what you see on a stage or in a website bio.

In Session lives on our site, and you can also watch on YouTube, Instagram, and LinkedIn. I hope these conversations serve as a helpful companion in your journey, something you can return to when you need perspective, encouragement, or one good idea to move forward.