Q&A with Jimmy Henderson, Director, Education Practice at Delivery Associates

Education is one of the most localized public policy challenges—designed and implemented within the unique cultural, economic, and political contexts of each country, state, or district. Yet, across borders, there is a growing global consensus: Education is fundamental to a nation’s productivity, social stability, and long-term economic growth. 

Despite this understanding, a significant gap persists between educational outcomes and workforce readiness. Alarmingly in the U.S., only 11% of postsecondary students feel very prepared to enter the workforce, and globally, by 2030, the United Nations estimates 60% of young people will be deficient in fundamental skills. This disconnect highlights the urgent need for education systems to equip students with both technical knowledge and essential soft skills to thrive in the evolving world. 

For Jimmy Henderson, addressing this challenge has been the focus of his career. As a former CEO, consultant, and venture strategist in education, he has worked at the intersection of policy, finance, and leadership development, helping schools, nonprofits, and governments design systems that don’t just promise impact but deliver it.

Now, as Director of the Education Practice at Delivery Associates, Jimmy is taking on a new challenge: helping governments and education organizations around the world bridge the gap between policy and outcomes. He will lead DA’s work in education, focusing on scaling evidence-based solutions, strengthening leadership pipelines, and ensuring that education systems—both in the U.S. and globally—are positioned to drive meaningful student success.

We sat down with Jimmy to talk about the state of education today, what works (and what doesn’t), and his vision for making change happen.

You’ve spent your career working to improve education systems—what drew you to this work, and what keeps you motivated?

I grew up in a rural community and attended a high school that did not serve all students well. I remember approximately 10 students in my graduating class of 125 matriculating to a four-year university.  

During college and in my first professional role, I met people who enjoyed a very different spectrum of post-high school options than my high school peers. That disparity really struck me as being arbitrary and unfair, and the consequences are significant from a long-term quality of life perspective.

It is a privilege to spend my career helping to change that dynamic for the next generations of students.

You’ve worked across many areas of education—charter school leadership, nonprofit management, financing, and strategy. What lessons from these experiences will you bring to your work at DA?

Sustainable change requires a deep understanding of how the status quo came to be, how organizations function, and how to overcome barriers to doing things differently.

A sound strategy addresses these (and other) topics with “point in time” information at hand.  Successful implementation, however, requires continuously monitoring these dynamics and course correcting across a wide range of tactics to make change stick.  

Doing this at scale is extraordinarily hard—and the greatest challenge in education. Yet this is the kind of pressing issue DA tackles. To quote Johann von Goethe, “A truly great talent finds its happiness in execution.” This is a big part of what draws me to DA and the work we do across the world. 

It’s helpful to remember that a large share of operating budgets in education (approximately 60%)  go towards personnel—so compared to other sectors, change management in education is about winning the hearts, minds, and habits of people.  

With this lens in mind—and to break through the ever-growing mass of emails, social channels, team communication apps, etc.—leaders must be increasingly disciplined in:

• Selecting a small number of priorities that will genuinely move the needle
• Investing an inordinate amount of time communicating “Why,” “What,” “How,” and “How it’s going”
• Monitoring progress, listening to their people, and course correcting quickly when things go off track 

In so many cases the people who work in education are incredibly passionate, creative, and committed to helping students succeed. Great implementation initiatives tap into this well of human potential and encourage the development of ideas and solutions at all levels of the organization.

The education sector is undergoing major shifts—AI, workforce readiness, new models of learning. What’s one emerging trend that excites you the most, and why?

Gen AI is the clear choice if I can only choose one, because the scope of its impact is both universal across the sector and has the potential to be deeply transformational. There is also an imperative for organizations to embrace AI now or risk falling behind in a structural way that will be difficult to remedy 3-5 years from now.

Harnessing the potential of AI requires a much more active “test and learn” approach at the individual, organizational, and system levels simply because the technology is evolving so rapidly. 

I see an opportunity for DA to help support a more robust, multi-tier approach to adoption and implementation with our partners.

You’ve led organizations and worked in entrepreneurial settings. How do you think about building high-performing teams, and what leadership principles guide your work?

Keying in on the word entrepreneurial, in my experience the best entrepreneurs are exceptional at: 1) creating momentum, 2) enabling others to find their passion and run with it, and 3) building a framework where team members can see how their work connects to the goals of the organization.

To create this type of environment, I strive to:

• Keep the team’s big goal—its “Why”—front and center 
• Foster personal relationships that serve as the basis for trust and joy
• Listen first, ask questions second, and then (maybe) speak third
• Celebrate wins and use setbacks as learning opportunities
• Share information quickly, liberally, and concisely

I’m also a big believer in old-school communication. A two-minute chat is better than a five-minute phone call is better than a 15-minute email. Give me a call anytime.

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Photo by Kimberly Farmer on Unsplash