Athena Bulletin

The Questions Tech Modernization Can't Afford to Skip

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By Cindy Gross

Questions are at the heart of successful projects — what gets asked, what goes unsaid, what assumptions have hardened into presumed facts long past their expiration date. In my years working with large enterprise accounts at Microsoft, I saw repeatedly that the things left unspoken were what derailed projects at the most inconvenient times. To get ahead of this, name the leadership debt and systemic friction early. Get curious about what needs to be thought through while it can still be changed with a small effort instead of a major rewrite later. That space and time can feel impossible on a tight deadline — but it's essential to avoiding delays, cost overruns, and systems that don't meet your needs.

Tech modernization projects are often designed around logic and process — as they should be. But logic alone doesn't account for the people doing the work, the ones who hold institutional knowledge, who know where the real friction lives, and who may be quietly carrying the weight of decisions they had no voice in making. When projects move too fast to make space for those voices, the system accelerates — but in the wrong direction. Assumptions go unquestioned. Processes get modernized exactly as broken as they always were. And the people who could have flagged the problem six months ago are either burned out or gone.

Washington State's IT Strategic Plan 2025–2028 names this directly: "Modernizing government is not only about upgrading technology. It also requires transforming how we work, how we lead, and how we support the people who deliver services every day." That's not a soft aspiration. That's a funded priority.

The plan goes further, calling for agencies to "invest in continuous learning, leadership development, and workforce readiness to support modernization and service delivery." The word continuous matters. A one-time offsite doesn't build psychological safety. A single change management training doesn't teach leaders to hold space for the question that hasn't been asked yet. Adaptive leadership capacity has to be built into the work, not bolted on at the beginning and forgotten by month three.

This is exactly where coaching earns its place in a modernization effort — not as a perk or a soft add-on, but as a structural component. A coach embedded in the work helps leaders slow down long enough to ask what's actually true, not just what's expedient. It surfaces the unspoken assumptions before they harden. It creates the conditions for the right people to speak, and for leadership to actually hear what they're saying. With tools like a 360 leadership assessment, it helps leaders redirect energy away from reactive patterns toward the creative competencies that move projects forward.

The result the Washington State's IT Strategic Plan is building toward: "Embed continuous improvement and change readiness into enterprise technology, workforce, and service efforts." Change readiness isn't a training outcome. It's an organizational capability — built deliberately, maintained actively, and worth as much to a modernization effort as the technology itself.

The questions that don't get asked in the room are rarely lost forever. They show up later — in rework, in resistance, in a go-live that technically launches but doesn't land. That's leadership debt compounding in real time. Building the leadership infrastructure to surface those questions early, to create the conditions where the right people speak and leadership actually hears them, isn't a luxury. It's the work.

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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.

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Appendix

Washington State IT Strategic Plan-8.27.25.pdf

“Modernizing government is not only about upgrading technology. It also requires transforming how we work, how we lead, and how we support the people who deliver services every day. That transformation begins by building a strong, adaptable workforce and fixing outdated processes that hold agencies back."

These are the most relevant strategic priorities –

• Create clear, statewide career pathways for technology roles, with a focus on training, mentorship, and advancement opportunities.
• Invest in continuous learning, leadership development, and workforce readiness to support modernization and service delivery.
• Embed continuous improvement and change readiness into enterprise technology, workforce, and service efforts.

The above PDF was found via Washington's IT Strategic Plan | WA.gov which was found via Washington releases updated statewide IT Strategic Plan for 2025–2028 | WaTech.