Why I Always Start With the People, Not the Plan
I've spent my career sitting at tables where the conversation usually starts with the technology, the policy framework, or the capital stack. At Google, at Dataminr, at Airbnb, and during my time as Chief Development Officer for the City of Detroit, I kept noticing the same pattern: the most sophisticated plans would stall, and the simpler ones would take off. The difference was almost never the strategy on paper. It was whether the people involved actually trusted the process and each other. That observation has shaped everything about how I approach my work.
The belief I keep coming back to is this: real results don't flow from the plan. They flow from the relationships and the trust that make a plan executable. I know that sounds simple. But it runs against how most institutions are wired. Governments want a framework first. Companies want a deck first. Everyone wants to show that they've thought it through. And thinking it through matters. But a technically sound idea with no human buy-in just sits there.
I saw this play out directly when I built Dataminr's AI for Good program. The technology was genuinely remarkable: real-time AI applied to crisis detection and early warning systems, with real potential to help humanitarian organizations respond faster to unfolding events. But no nonprofit or human rights organization was going to hand over access to their workflows or trust an AI system just because the pitch deck was compelling. So I started with conversations, not proposals. I asked what they were actually trying to do, where their teams were burning out, what tools had failed them before. The program grew because the relationships came first.
At the City of Detroit, the stakes were higher and the skepticism was earned. When you're trying to mobilize investment into neighborhoods that have seen decades of disinvestment, you don't get to walk in with a slideshow and expect people to line up. Community members, local business owners, and government partners all had different histories with "plans" that never materialized. So my team spent time listening before we spent time presenting. That's not a soft skill. That's a prerequisite for getting anything done in a complex environment.
This approach shapes how I build teams, too. I look for people who are curious about context, not just execution. A person who asks "why does this community need this" will outperform one who only asks "what's the deadline" almost every time. At Google, I led teams that ranked first globally on performance metrics. I don't think that happened because we had the best tools or the most resources. It happened because people on those teams understood what they were working toward and felt accountable to something beyond the quarterly number.
There's a practical discipline that comes with centering people before plans. It forces clarity. When you have to explain something to a city council member, a nonprofit director, and a venture-backed technology company in the same week, using language that actually lands with each of them, you can't hide behind abstraction. You have to know what you're actually trying to do. That discipline has made me a better thinker, not just a better communicator.
My education reinforced this instinct. At Harvard Kennedy School, studying public administration put the question of who benefits and who bears the cost at the center of every policy analysis. That framing never left me. It shows up every time I'm evaluating a public-private partnership or helping a government think through a technology adoption decision. The question isn't only "does this work?" The question is "for whom, and under what conditions?"
What I hope to carry forward is a continued insistence on that question, especially as AI becomes more embedded in how governments and organizations operate. The technology will keep advancing. But the human judgment about where to apply it, who to involve in the design, and whose trust needs to be earned first: that judgment doesn't automate. I think the leaders who get that right, early, will do the most durable work of the next decade.