Small Wins, Systems Change, and the Challenge of Leading from the Inside

Last week, the Aspen Institute Economic Mobility Fellows gathered for our second seminar in New York City. We started at Hot Bread Kitchen’s training facilities in Chelsea, then walked the High Line to KKR’s offices in Hudson Yards to meet with several program alumni. It was a crisp, sunny morning, and the walk gave physical expression to a tension that would run through our gathering: the relationship between efforts to expand economic opportunity and the larger economic system that shapes it.

Our Fellows are passionate about economic mobility and committed to using business to advance it. Yet they work within companies and systems that, to varying degrees, also perpetuate the inequality they seek to address. I share that tension. At Aspen, our work supports leaders working within an economic system that produces deep inequalities. That reality invites us all to ask: How do we change systems we help sustain? What does it mean to lead within a system that feels not only flawed, but increasingly frayed?

Those questions surfaced repeatedly in various forms. One Fellow put the dilemma plainly: “I never get to touch a root cause. I am only dealing with symptoms.” That same Fellow, however, also emphasized that addressing those symptoms has real, material impact on thousands of people. Both things are true. The challenge is to hold them together without retreating to a narrow interpretation of our projects or concluding that nothing short of wholesale change matters. The task we face, it seems, is to understand how we address immediate needs while also influencing the conditions that make those needs so persistent.

One week earlier, our First Mover Fellows explored similar questions through a long-standing second-seminar reading: Karl Weick’s 1984 article, “Small Wins: Redefining the Scale of Social Problems.”  Weick describes how bounded, achievable interventions can make overwhelming problems actionable by creating opportunities to generate learning, mobilizing support, and revealing new opportunities. His work offers a useful lens on our conversations, and a central provocation: What makes a small win strategic?

One answer lies in the connection between a project’s immediate impact and what it makes possible further down the line. A project might expand opportunity for employees while building evidence for a practice other employers could adopt. It might challenge assumptions about workers, build a constituency for reform, or help make a previously untenable policy possible. Of course, a successful project does not automatically produce these wider effects. Pursuing them requires deliberate choices about how a project is designed, whose knowledge informs it, and how its lessons travel beyond its initial scope.

For intrapreneurs, this means taking a more expansive view of their influence and being specific about where it offers leverage. And it invites a similar view for those of us supporting their work: While we help Fellows deliver successful projects, are we also equipping them to recognize and pursue opportunities for systemic change?

We don’t need to resolve every contradiction in our positions before we act. But wrestling with those contradictions is part of the process. Helping thousands of people navigate a broken system has considerable value. When our ambition also includes changing that system, we owe ourselves—and the people we aim to serve—a clearer account of how the small wins we pursue might contribute. Taking that obligation seriously is what effective leadership demands in this moment.