Who's In Your Trust Chain?
By Cindy Gross
A colleague asked me a question recently that I haven't been able to shake: "How do you lead in a world where you can't trust things?"
She was naming something precise and important — something a lot of leaders are carrying right now. Not because they distrust AI, but because they feel the pressure to use it regardless of their questions about it. The questions are real. The pressure to move forward anyway is also real. And most organizations haven't built the infrastructure to hold both of those things at once.
AI has entered most organizations silently, without waiting for a policy or a plan. And the chain of what we trust — and why — has shifted in ways most organizations haven't stopped to examine. Consider how quickly it compounds: a project lead frames a question with AI assistance, an analyst pulls data the same way, a program manager shapes a strategy on top of that, and a director makes a consequential decision at the end of the chain. Each step felt responsible. Nobody flagged it because nothing felt wrong. But one wrong assumption, introduced quietly three steps back, distorts everything downstream. The compounding is invisible — until it isn't.
This is not primarily a technology problem. It's a leadership and governance problem. The question isn't whether AI should be used. It's whether anyone in the chain knows where their confidence actually comes from. Whether the assumptions underneath a recommendation have been named. Whether the people closest to the impact had any voice in the decision that affects them. The pace of technology modernization rarely leaves room to ask what's still true — and what needs to stay true. When those questions go unasked, leaders are making decisions on foundations they can't fully see.
Washington State's IT Strategic Plan 2025–2028 already reflects this reality: "Embed continuous improvement and change readiness into enterprise technology, workforce, and service efforts." Change readiness requires knowing what you're confident about and what you're not. You can't build it on a trust chain nobody has examined.
The same diagnostic rigor that technology leaders apply to systems — auditing assumptions, mapping dependencies, stress-testing reliability — belongs on the human side of the trust chain too. Who is making decisions? With what information? Under what pressures? Where is energy going that could be redirected toward the outcomes that actually matter? Structured diagnostics, calibrated to the specific organization, project, and people involved, surface these patterns without judgment. They separate internal friction from external structural reality. They identify where a shift in approach would change what flows downstream — before it compounds into something harder to untangle.
This is an emerging challenge without a tidy solution. But there are ways to navigate it with more clarity and confidence than most organizations currently have. It starts with creating the conditions for honest examination — psychological safety as decision-making infrastructure, not a culture initiative. It means bringing in people who weren't in the room. It means building a strategic bridge between mission, people, and technology that holds up under pressure. When those conditions exist, leaders stop performing certainty they don't have and start building confidence they can actually stand behind.
How much visibility do you have into your trust chain? That's not a question about whether your people are trustworthy. It's a question about transparency —whether the assumptions shaping your most critical decisions are visible, named, and examined before they compound into something harder to correct.
We're paying close attention to how this challenge is evolving — and bringing the leadership, governance, and coaching expertise to help modernization teams navigate it thoughtfully. That work looks different in every organization. But it always starts with the same question: what do we actually know, and how do we know it?
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For more information, check out our Tech Modernization services.
Cindy Gross (she/her) is an executive coach, facilitator, and leadership systems strategist with 25+ years in tech, including 18 years at Microsoft. She specializes in helping leaders and organizations navigate complex change with clarity, equity, and durable results. Learn more about Cindy's work and her Leadership Navigation System — built for leaders who are ready to navigate complexity without losing themselves — at BefriendingDragons.com.
Cindy works in collaboration with The Athena Group, a human-centered technology modernization consultancy serving state and local government leaders. Learn more at athenaplace.com.
