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Sally Osberg joined the Skoll Foundation– which was created by Jeff Skoll, the first employee and first president of eBay – as employee number one in 2001 and subsequently became its first president and CEO. She stepped down from that position earlier this year.
During her time at the helm, Osberg oversaw the philanthropy’s investment in more than 100 entrepreneurial organizations worldwide. She also led Skoll through three distinct phases – “startup,” “get going and do it,” and “renewal,” to use her terms – that reflect her approach to leadership. “You’re always sowing new seeds,” she explained. “The world is changing, and you have to adapt.” In this vein, Osberg and her colleagues initiated new platforms intended to connect civil society and public and private sector leaders with societal problem solvers. These platforms include the Skoll World Forum on Social Entrepreneurship, the Skoll Centre for Social Entrepreneurship at Oxford University’s Said Business School, and the Stories of Change initiative at the Sundance Institute. Osberg also published numerous articles and co-authored with Roger Martin the 2015 book Getting Beyond Better: How Social Entrepreneurship Works.
Osberg remains active in the social sector. She currently serves as associate fellow for the Skoll Centre for Social Entrepreneurship at Oxford’s Said Business School, as chair of the Camfed (the Campaign for Female Education in Africa) USA Foundation, as a board director of the New America Foundation and the Social Progress Imperative, as chair of More in Common, and on the advisory council of The Elders (an independent group of global leaders working for peace and human rights), among other roles.
Recently, Osberg took time to share with us her views on strong leadership. Although her wisdom springs from her many years in the social sector, much of it applies equally well to the private sector.
Be clear about strategy
“No social sector leader can be effective without a strong sense of purpose and a well-articulated and well-honed strategy,” Osberg said. “You can’t do everything. A lot of leadership goes sideways when it tries to take on too much, or respond to every need that is out there.”
A good leader must also recognize that an organization’s strategy may need to change over time. “At the Skoll Foundation, very early on we were clear about needing to evolve our strategy. We [updated the strategy] about three years in, when we had enough experience under our belts,” Osberg said. The strategy that her team, together with Jeff Skoll, eventually developed – to drive large-scale change by investing in, connecting, and celebrating social entrepreneurs and the innovators who help them solve the world’s most pressing problems – became the Foundation’s stake in the ground.
Accept complexity
Challenges are like nesting dolls: Inside every challenge is another challenge. The social sector is, by definition, especially challenging. “Societies are informed by culture, geography, history, people, dynamics in the world. They’re inherently complex,” Osberg explained. Every individual, too, “is an incredible bundle of complexities,” she added. As a leader, Osberg had to accept complexity, learn to adapt, and make peace with the fact that things would not always go as she intended.
Embrace the leadership strengths of women
As a leader, Osberg learned to embrace her strengths and to use them. One critical strength is that she is a woman. Women leaders, she argued, are often particularly adept at “integrative thinking,” referencing the frame developed by Roger Martin and fleshed out in his 2007 book, The Opposable Mind: How Successful Leaders Win Through Integrative Thinking:
The ability to integrate what may seem like oppositional ideas, perspectives and options is a real strength of mine and a strength I believe is common to many women leaders,” she said. As examples she cites the ability to be simultaneously ambitious and humble and the discipline of listening deeply—paying as much attention to what’s not said as what’s voiced. It’s particularly important, she noted, to listen to “the women at the table, in the organization, in your community” and to “consult with them, invite them to share their perceptions so as to cultivate a greater diversity of ideas.”
Brand for strategic identity
When Osberg took the helm at the Skoll Foundation, she thought branding was all about “color palette, logo, font, and bragging about the value that you provide,” she recalled. She did not think such investment was appropriate to a social sector organization. “I thought branding was for corporations with money to burn,” she explained. “I thought it was not really relevant when you are trying to contribute to the common good.”
Jeff Skoll, however, thought otherwise and was insistent that his foundation should create a strong brand. Initially, Osberg said, she approached the matter in a perfunctory way, and when she gave her first presentation on branding, her recommended approach promptly “got shot down by Jeff and by the folks serving on the Foundation’s initial marketing and communications committee.” She then went back to the drawing board and with the help of consultant Noah Manduke began to understand that branding is about strategic identity. “It is clarity about the differentiated value you deliver to the world, and it’s only valid if your audience on the receiving end of that value actually perceives it to be valuable. It’s really a dialogue with your customer, your clients, those you serve. And once I learned that, then I embraced it,” Osberg said.
Recognize that a good board is priceless
During her 17 years at Skoll, Osberg developed a strong appreciation for her board. Every member of the Skoll board, she said, was “a real student of effective governance.” Members of the board were all highly experienced fiduciaries with great integrity and rich experience who regularly rose to whichever challenges the foundation faced. “If I had a magic wand and could wave it, I would want every leader to have the benefit of a really, really good board,” Osberg said.
Absent that wand, leaders have to work to build a great board or, in some instances, transition to one more capable of effective governance. To this end, Osberg developed what she called “the airplane seat rule”: She strove to attract and retain board members who she knew would mention the Skoll Foundation if they began chatting with someone on an airplane. “That’s because they are dedicated to serving Jeff and his vision and proud of their association [with Skoll]; they understand and appreciate the work well enough to want to share it,” Osberg explained. “A board member who isn’t going to take that kind of time, or who isn’t really invested in the work and the performance, is not going to be a great board member.”
Stay rooted in your values
“Effective leadership is always rooted in a strong sense of values,” said Osberg. The Skoll Foundation’s values, she explained, grew from Jeff Skoll’s vision and his “profound sense of responsibility, [his] desire to make change in the world, and [his] sense of urgency.” These values were absorbed by the entire organization and became part of its DNA. They were augmented by the wisdom of John W. Gardner, founder of Common Cause and Independent Sector—specifically his teachings on “tough-minded optimism.” “So we’re incredibly optimistic about the potential for the world,” Osberg said. “At the same time, we’re driven by reality and the need to be rigorous, because the challenges are many and they’re morphing. It’s easy to feel overwhelmed sometimes, but that tough-minded optimism always served me and the foundation well.”
