Real-World Strategies for Managing Risk and Delivering Impact During a Legacy IT Overhaul
The "Working Backwards and the Messy Middle" session block at Prodacity 2025 tackled a critical challenge in government and enterprise: navigating the uncertainty of modernization while ensuring effort delivers mission value. The speakers—Jason Fraser, Nick Kuene, and Josh Kruk—provided practical insights into working backward from mission outcomes, balancing modernization with risk, and managing complexity in legacy and new systems.
Here are four major takeaways from the session block:
1. Working Backward: Maximizing Impact with the Mission Ratio
"A day at work could mean saving thousands of lives instead of saving just one." – Jason Fraser (on Max's realization at Kessel Run)
The Mission Ratio: Doing Good, Better
Jason Fraser introduced the Mission Ratio, a powerful way to measure how well an organization turns resources into mission outcomes. His story of Max, a pararescue Airman turned software engineer at Kessel Run, illustrated a crucial lesson: leverage matters more than effort.
- In pararescue, Max could save one life per jump.
- In software development, he could build tools that saved thousands of lives at scale.
This is the essence of the Mission Ratio:
- Input → Outcome → What you put in vs. what you get out.
- Constraints Define the Leverage Point → Identify bottlenecks that limit mission effectiveness.
- Kill the Zombies → Projects that don’t contribute to mission impact waste resources and create drag.
"Your organization is a mill for turning resources into mission outcomes. If zombies are sucking up resources, real people are suffering as a result." – Jason Fraser
Why This Matters for Government & Federal Tech
Government teams often get stuck measuring activity instead of impact. Instead of tracking:
❌ How many software releases did we push?
✅ How did our software quantitatively improve mission outcomes?
Fraser’s framework provides a way to measure whether efforts are truly moving the mission forward—a must for agencies working under budget constraints and political scrutiny.
2. Modernization Without Failure: Managing Risk in the Messy Middle
“If AI hallucinates your business rules, you don’t have a business anymore.” – Nick Kuene
The False Choice: Modernize or Do Nothing?
Nick Kuene tackled the tough modernization challenge of decades-old legacy systems that still run mission-critical operations. Agencies often feel trapped between:
- Massive, high-risk modernization efforts that fail more often than they succeed.
- Leaving legacy systems untouched, which leads to growing costs and risks.
Neither approach is sustainable. Instead, Kuene proposed a confidence-driven approach to modernization:
- Capture system behavior before changing anything. Your legacy system already produces significant data—use it to understand how it works.
- Build a behavioral twin. A modern system should mimic the original’s outputs 1:1 before adding new features.
- Verify deterministically. Don’t trust AI or automation blindly. Measure every change against known behaviors before deployment.
The Role of AI in Modernization
AI won’t magically rewrite your legacy systems, but it can help. Kuene emphasized a key rule:
“Trust, but verify.” Let AI propose solutions, but ensure they match real-world system behavior before deployment.
For government agencies sitting on decades of COBOL, FORTRAN, and other legacy code, this approach offers a way to modernize incrementally without catastrophic failure.
3. Delivering Business & Mission Value in a Complex System
"The biggest failures in my career have been when we had one team working on the old system and another team working on the new system—hoping they’d magically meet someday." – Josh Kruk
Iterate, Don't Rebuild from Scratch
Josh Kruk, who leads digital at Kohl’s, provided a real-world example of balancing legacy systems modernization with delivering value today.
His insights apply directly to government and defense programs dealing with aging IT infrastructure:
- Don't chase modernization for the sake of it. Some old systems still work well. Focus on areas that create bottlenecks.
- Have the same team own both old and new systems. This prevents handoffs, silos, and disconnects between strategy and execution.
- Deliver something real every six months (or faster). If a project takes longer, the market, mission, or priorities will change before you finish.
"If you can't see results in the real world in six months, you're doing the wrong thing." – Josh Kruk
Practical Signs of What to Fix First
Kruk offered two ways to identify the most valuable modernization targets:
- How many people have to talk before deploying a change? Too many approval levels indicate you have a process problem.
- Where are people constantly working around inefficiencies? The biggest workarounds usually indicate the biggest opportunities for impact.
For government agencies managing long procurement cycles and multi-year projects, this forces prioritization for impact.
4. How to Work Backward from Mission Value (Without Getting Stuck in the Middle)
"You need to start with what the mission actually needs—not just what tech teams want to build." – Josh Kruk
Start with the End in Mind
A common theme emerged during this session block: many organizations get lost in execution without clearly defining success.
Working backward ensures every effort starts with a clear understanding of mission value before investing in execution.
- If you can’t measure mission impact, don’t do it.
- If a project isn’t improving mission effectiveness, cut it.
- If teams are optimizing for the wrong metrics, realign them.
How to Stay on Track in the Messy Middle
Kruk emphasized that the hardest part of transformation isn’t starting or finishing—it’s the middle, where teams:
- Hit organizational resistance.
- Struggle to balance old and new systems.
- Get caught in never-ending migration efforts.
To avoid getting stuck in the messy middle, successful teams:
- Ship small, measurable improvements constantly.
- Test impact, don’t assume it.
- Make sure every investment has a clear ROI, either in dollars or mission outcomes.
"You can optimize for local wins while hurting the broader mission. The key is knowing when you’re doing that—and stopping it." – Josh Kruk
TLDR; Takeaways for Federal Agencies & Contractors
- Use the Mission Ratio. Focus on outcomes per unit of effort, not just activity.
- Modernize incrementally and measure confidence. Capture behavior before rewriting legacy systems.
- Make the team building the new system responsible for maintaining the old one. This prevents silos and keeps teams accountable.
Don’t get lost in execution. Start with mission outcomes and constantly test whether work is delivering impact.
About the Prodacity 2025 Blog Series
This blog is part of a series which distills insights from talks at Prodacity 2025. This entry covers the session block "Working Backwards and the Messy Middle," featuring Jason Fraser, Nick Kuene, and Josh Kruk. Want these insights and other Prodacity announcements delivered straight to your inbox? Subscribe here.
