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Strategy Advising
I help you make sense of AI, navigate uncertainty, and facilitate change in your system.
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The pace of tech change is disorienting — your system feels more uncertain than ever.
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AI hype hides what really matters — the people, relationships, and power dynamics you’re trying to shift.
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'AI expertise' isn't enough. You need to understand how AI is entangled in social systems and design responsible strategies that takes advantage of what machines do brilliantly while protecting what makes us irreplaceably human.
I help clients develop AI strategies that map to their vision of the future while navigating uncertainty, AI policies that reflect their values while addressing tradeoffs, and ensure these ideas make it off the page and into organizational practice.
Clients & Course Participants
As a facilitator and strategist, Charley skillfully pulls out diverse perspectives and comfortably navigates areas of strategic divergence. If you want help coalescing around a new future direction or change agenda, he is your guy!"
Charley is a next-generation strategist and facilitator who builds generative connections across sectors, ideas, and people with different perspectives and backgrounds. He is simply an incredible partner for empowering communities to make progress against complex problems."
Charley's strategic thinking, high EQ, deep listening skills, and ability to ask incisive questions help cut to the heart of complex and challenging group dynamics, while moving the group toward impact."
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My Approach
My approach is tailored to the unique challenges of leaders and organizations. It is grounded in years of experience stewarding multi-stakeholder, systems change initiatives at Data & Society Research Institute and as the Director of the Center for Digital Development at USAID. I draw on my expertise in sociotechnical frameworks and formal training in complex adaptive systems with Dave Snowden at The Cynefin Company and The Sante Fe Institute for Complexity.
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Systems Not ' Tech Solutions': Philanthropies and civil society groups often feel pressured to develop “AI strategies,” but start with the technology instead of the system they’re trying to change.
I help leaders flip that script — focusing first on the future they want to create, then mapping backward to see how AI might help or hinder progress. The real question isn’t “What’s my AI strategy?” — it’s “How can I change my system?”
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Collective Sense-Making & Action: In any system shaped by AI, funders, grantees, policymakers, and technologists bring different values, incentives, and frames of meaning.
I help organizations create spaces for translation across those differences—surfacing assumptions, building shared understanding, and enabling real coordination and collective action.
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Strategy As Living Practice: Many organizations still treat strategy as a fixed plan — but in complex systems, conditions shift faster than any roadmap can adapt.
I help teams treat strategy as a living practice—adapting toward your future vision and in response to signals in your system, building trust, holding difference, and turning conflict into shared, continuous learning.
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Systems Change When Relationships Change: Traditional strategy processes often overlook the relational and cultural foundations of systems, treating trust, power, and relationships as abstractions instead of the real levers of change.
I help organizations see how relationships shape behavior and alignment—revealing where systems are stuck and where shifts in culture or connection can unlock new possibilities.