Today leadership is about visibility and being authentic. Earlier this year, I attended a session with my favorite living poet, David Whyte, who inspires us to be vulnerable in being ourselves. I have followed his writing and enjoyed his workshops for many years. This session included a most intriguing organizational expert, Gayle Karen Young, who I was totally taken by. I found her perspective on leaders finding their way in this messy organizational life quite mind shifting.
Gayle brings wisdom and warmth to the conversation about how we develop as leaders within complex and changing systems. She calls herself a “rogue provocateur.” Join me in our fascinating conversation about how we thrive in this unpredictable place called leadership.Sherry Benjamins: Tell us about your perspective on leadership today.
Gayle Young: Its been fascinating to watch my own thoughts on leadership and culture evolve as I’ve moved from being an external consultant to taking on a role as Chief Talent and Culture Officer (essentially the CHRO) at the Wikimedia Foundation, and then going out on my own again.
For background, the Wikimedia Foundation is a fascinating organization for being one of the top five visited websites in the world. It’s the only top 50 website that is a non-profit. The actual organizational size is small, but a huge number of volunteers help run it and essentially create the product. Each language has their own Wikipedia and governing bodies. The volunteer base influences a lot of the dynamics. We worked in more of a network or influence-based structure.
Any dynamic that impacts the geopolitical news landscape, shows up on Wikipedia. Whether it was a downed flight in Ukraine or conflicts in South America, you can see ideological differences pop up across different wikis. It taught me a lot about complexity, permeability, culture, and of course, the day-to-day of business management like performance, quarterly goals, large implementations, etc.. I grew to have an appreciation for the intersection of complexity and organizational development and culture.
Being a leader in these contexts for me means having a capacity to work both the mythic and the mundane. It requires working on the mission, the values, the intangibles, and the day-to-day experiences that become tangible components that nudge a complex system in a particular way, like the way that decisions are made or that meetings are run. I say “nudge” because I believe that we don’t get to manage culture. We do small things that ripple through a system in profound ways.
SB: You’re now collaborating with fascinating leaders and companies. What made you decide to go out on your own?
GY: I was at the Wikimedia Foundation for four years and I loved it. It was a great place to practice leadership and my own mission. I was working with one of the executive directors, Sue Gardner, who I would follow anywhere. There was a leadership transition where the organization didn’t need me in the same way and I had personal needs that led me to take a year off. At that time, I was at a retreat at the Burren Executive Leadership Program, which aimed to foster a leader’s action by way of reflection. That’s when I first met David Whyte, who was an artist in residence. It changed the course of my life.
SB: Tell us about what you do to help a leader with running their company?
GY: I do have one-on-one coaching with clients where we reflect on their own practices of leadership. I also work with executive teams. Sometimes I go in and support a new team as it’s coming together. We explore how do they lead together? What does collective leadership look like? A team that’s high-performing doesn’t just do their own thing and then come together. They practice what they want to do.
I also have my passion projects. I work with an organization called Hidden Leaf that offers grants for personal development for social justice leaders, or I work with organizations like Uncharted, that supports social entrepreneurs.
SB: What would you say to a CHRO today about their leaders and the organization of the future?
GY: I think it starts with understanding the evolving nature of the workforce and it’s an interesting one. There’s an upsurge of people looking for meaning. A lot of Millennials tend to be part of the compulsive-awesome generation. In terms of designing work and roles, people are asking, “what is their evolving portfolio of their skill set?”
An organization’s culture is a nested set of environments. If you’re going to understand the culture of Wikimedia, for example, you have to understand the values of the Enlightenment and the spirit of the Gutenberg Press, as well as seeing that it is rooted in the ethos of the free knowledge movement and in the open nature of the internet itself. Those streams of values, norms, and beliefs are part of the operating ecosystem. A CHRO can understand and track the streams that are influencing an organization’s culture.
SB: How do we start to see the often subtle influences at play when understanding what influences us?
GY: If you’re going to try to understand yourself, try to understand the contexts you emerge from as a beginning. I’m an immigrant with a Chinese family, raised in California. Each of these things gives a window into what makes me up. In that way Toms Shoes would be influenced by philanthropy, the shoe industry, manufacturing, and its location in Silicon Beach. It’s like mapping out what all the elements are of being you, but at an organizational level.
SB: As we reflect on who we want to be as leaders, are you seeing more partnership between CEO’s and HR?
GY: If you're CEO doesn’t get you and has a traditional view of HR, in other words, a compliant-based version of HR instead of a development-based version, that makes for a very difficult relationship and forward thinking partnership. Particularly if the CEO doesn’t appreciate and value and support that function, it is almost a non-starter.
SB: I attended the workshop that you and David did together and I’ve followed David’s work for over 20 years. He facilitates new conversations that guide personal development. . Do you see executives investing in this way?
GY: If you want people to follow you with a kind of whole-hearted engagement, then personal development and professional development are inextricable. One metaphor is the difference between a hollow core and a robust one, and that IS visible in the world whether you know it or not. As a leader, by the very of nature of leadersihp, you must have a willingness to really be seen. What you’re seen as standing for, since every movement you make is watched and noted on, as an active, conscious choice, makes all the difference in the world. That’s where the self-knowledge comes in. With the work David does, he helps get us to be grounded in our own robust vulernability. But we have our own work to do to understand how we want to be seen in the world, what we stand for, and what we live out. It’s this notion of when you’re unaware of what you put into the world, Jung said, “that which remains in the unconscious comes back to us as fate.” Unless you work with your own interior landscape, then you don’t have a hope of influencing what it is that you invite.In closing...We are in a time when doing the “internal work” of a leader is seen as high value, yet many find it challenging to accomplish. Gayle’s refreshing and honest perspective encourages us all to dive in to move forward. Clearly, the benefits of finding a friend or coach to help you in your leadership journey are invaluable.