💫 Executive coaching & advising

Executive Coaching

Hello, Freedom!

​I help leaders like you facilitate change -- in yourself, your organization, and the system you work within -- and live more impactful and freer lives.

​Sometimes this looks like executive coaching. Other times, it might look like strategic advice. In either case, here’s how it works:

• 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.

Testimonials

• "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

My approach to executive coaching

My superpowers are listening deeply and asking incisive and open questions. But some coaches only ask questions because they want you to come to the answer on your own. I get it, but that’s not me. Only ever asking questions would mute my other superpower: systems-informed, strategic thinking.

​I’ll listen and reflect back what I hear, but if I have a perspective or advice, I won’t hide it. I’ll proactively share what I think, and if it resonates with you, great. If not, that’s great too! We’ll go back and forth, co-creating alternative hypotheses and approaches as partners.

I’m currently taking on a limited number of clients, and offer these services in one-month, three-month, and six-month packages. 

Advising

If you work for a civil society, government, or a philanthropic organization, that’s the question of the moment. But it’s a dangerous one that will lead you astray. Here's why:

1. Technology is not a north star. It’s not a vision of the future you want to create. AI is an especially problematic starting point because it and other data-driven technologies can encode past inequitable patterns in the present. Technology might be a piece of the puzzle, but the sociotechnical problem you’re trying to solve and the future you’re trying to create should drive your approach.

​2. Strategies shouldn’t look forward, they should map backward. The future is not a neat ‘theory of change’ away. All technologies are entangled in social systems (e.g. race, gender, power, etc.), which are complex, and don’t often adhere to cause-and-effect. Your strategy must be clear-eyed about these complex dynamics, and map backward from the future you want to create.

​3. ‘Your’ assumes that you can do this alone. You can’t. Shifting systems and building new futures requires collective action, which in turn, hinges on collective sense-making. It requires getting on the same page about the complexity of the problem across diverse stakeholders, the future the group wants to create, and how to get from here to there.

​As an expert in sociotechnical systems, strategist, and facilitator, I’m here to help you realize your vision. I offer a range of advisory services, including strategy development, visioning and world building, coalition and partnership design, and sociotechnical analysis.