EP · 011
THE SCIENTIST WHO BET HIS CAREER ON BUGS. 14 YEARS LATER, HE WAS RIGHT.
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You spend 90% of your time as a CIO building relationships and coalitions. Because that's the only way stuff gets done.
Ann Dunkin
Ann Dunkin on what it takes to modernize technology in a massive government bureaucracy, why the hardest problems are never technical, and what she learned leading through resistance and skepticism.
Key Takeaways
- →Government technology leadership is fundamentally a people problem: Ann found that the hardest part of modernizing government technology was never the technology itself—it was the humans: the resistance to change, the institutional inertia, the fear of failure in public service environments.
- →CIO of a state government means serving millions of people with underfunded systems: Ann's scope wasn't a single company—it was an entire state government with dozens of agencies, billions of dollars of legacy infrastructure, and constituents whose lives depended on systems working correctly.
- →Technology modernization requires political skill, not just technical skill: You can have the best technical plan in the world and fail completely if you can't build coalitions, navigate competing interests, and bring skeptical stakeholders along. Ann learned that technology leadership at scale is political leadership.
- →Legacy systems persist because they work, not despite it: The most persistent legacy systems are the ones that have been doing their job reliably for decades. That reliability is exactly what makes replacing them so difficult: you have to be better than something that works, while also not breaking anything in the process.
- →Risk tolerance in government is structurally lower than in private sector: Government technology projects fail publicly, affect millions of people, and create political liability. That risk profile creates a conservatism that sometimes prevents good decisions—but understanding why it exists is the first step to working within it.
- →Women in senior technology roles still face a particular kind of scrutiny: Ann navigated both the technical and the social dynamics of being a woman in a senior technology leadership role. She describes the additional credibility tax and the specific communication adaptations she developed to be heard in environments that defaulted to skepticism.
- →The hardest part is sustaining change after you leave: Building something matters; making it sustainable without you matters more. Ann focused intensely on building teams, processes, and cultures that wouldn't require her continued presence to maintain the progress she'd made.
Full Essay
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Questions answered in this episode
What does a state government CIO actually do?
A state CIO oversees technology strategy and infrastructure for an entire state government—typically dozens of agencies, hundreds of systems, and services that millions of citizens depend on. Ann's role included modernizing legacy systems, implementing cybersecurity standards, managing enterprise software, and building a technology workforce capable of serving the state's future needs.
Why is modernizing government technology so difficult?
Ann identifies three structural barriers: risk aversion (failure is public and politically costly), legacy dependencies (old systems that work and are deeply embedded), and resource constraints (government rarely has the budget to modernize as fast as the private sector). The hardest barrier is cultural: changing how people think about technology in environments that have survived by being conservative.
What skills do you need to succeed as a technology leader in government?
Technical credibility is table stakes—you need enough depth to earn the respect of your technical teams. But the differentiating skills are political: coalition building, stakeholder management, the ability to translate between technical and policy languages, and the persistence to keep pushing change through bureaucratic resistance.
How do you manage people who are resistant to technology change?
Ann's approach: start with the problem they care about, not the solution you have. Most resistance to technology change is actually resistance to risk or to loss of control. Understanding that lets you address the actual concern rather than the stated objection.
What is it like to be a woman leading technology in government?
Ann describes a specific dynamic: higher scrutiny of technical credibility, more need to prove that intuitions are backed by data, and occasional underestimation that she learned to use strategically. She also credits the government culture—more diverse than many private sector tech environments—with creating more space for women in leadership than she had expected.
What happens to technology modernization after a CIO leaves?
It either continues or it doesn't, depending on how much the change was institutionalized versus personalized. Ann focused on building the infrastructure of change—teams, processes, culture—rather than relying on her personal authority to sustain progress. The ones that stuck were the ones that were embedded in how the organization worked, not in what she insisted on.
How do you make the case for technology investment to non-technical government leaders?
In terms of constituent outcomes and risk, not technology features. Politicians and senior administrators care about whether services work, whether data is secure, and whether the state is exposed to liability. Translate your technical priorities into those terms, and you'll get a hearing. Lead with the technology, and you'll lose the room.
About Ann Dunkin
Ann Dunkin is a technology executive and former state Chief Information Officer who has spent her career modernizing government technology infrastructure. She brings both deep technical expertise and hard-won political skill to the challenge of making government work better for the people who depend on it.
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