💫 Advisory Practice

Strategy Advising

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.

• 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?”

• 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.

• 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.

• 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.

Fill out this form to get free access to the framework I created to assess an organization’s capacity to navigate uncertainty and complexity. Click here.

Facilitation

We’ve all been in stuck meetings that fail to achieve their goals, planning processes that are hijacked by conflict and/or unproductive group dynamics, and strategy retreats that focus on all the wrong issues.

I help organizations:​

• Develop actionable and purposeful strategies that address the roots — not symptoms! — of organizational challenges.​

• Implement intentional planning processes and high-value meetings, and navigate high-stakes group decisions.​​

• Make productive use of difference and conflict, and release unhealthy group dynamics.

I offer interactive courses, skill-based workshops, and organizational training.

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1:1 Leadership Coaching

My superpowers are deep listening and incisive, open questioning—but unlike some coaches, I don’t stop at questions. Only asking would mute my other strength: systems-informed, strategic thinking. I’ll reflect back what I hear and share my perspective. If it resonates, great; if not, we’ll refine it together—co-creating new hypotheses and approaches as partners.

What it looks like in practice

• We identify your personal and/or strategic goals together.

• We untangle all the stuff getting in the way — the complex interpersonal, strategic, and organizational dynamics — session by session.

• I share my reflections after each session and offer homework and/or strategic guidance for your consideration.​

Nuts & Bolts

• 3-month commitment to ensure meaningful progress and give us concrete check-in milestones.

• 60 Minute Sessions - Two 1:1 sessions per month (minimum)​

• Email & text support between sessions.

• Ad Hoc Sessions - For urgent opportunities or challenges (within reason, at no extra cost).

What my clients say

• "Charley's superpower is listening. He listened closely to me in order to help me find ways to navigate immediate challenges while keeping my focus on my longer-term aspirations. I found it especially helpful to have Charley's written follow-up documenting our work together. In doing so, he demonstrated the depth of his insight into my unique situation and compelled me to work harder to take full advantage of these special coaching sessions." Priya Vora, CEO, Digital Impact Alliance

• "I needed a coach to help me work through various strategic decisions at TechChange and to help me identify more opportunities for better work/life balance. Charley is/was a fantastic match for me. He’s an excellent listener, adept at reframing problems, and even designed practical exercises that I found extremely useful in my journey. Nick Martin, CEO, TechChange.

• “Working with Charley on career development was a total delight. Charley always listened thoughtfully, drew out the concerns I had below the surface, and brainstormed constructively on paths forward. He really helped me turn my rough ideas of what I wanted to do next into a clear plan for getting the job I wanted.” Jake Porway, Founder & Executive Director, DataKind