Too often, execution breaks down because it ignores frontline friction. The reflex is often to treat non-compliance as defiance or disengagement, when in reality, it’s often a signal.
Leaders often launch new strategies with high hopes, only to end up managing compliance rather than enabling real change. The challenge isn’t crafting a compelling vision; it’s ensuring that the vision can be adopted and implemented by the people closest to the work.
Richard Rumelt, in his landmark book Good Strategy, Bad Strategy, wrote:
“The most common path to bad strategy is avoiding the hard work of diagnosing the real problem.”
When we skip diagnosis, we focus on what should happen instead of what is happening. Leaders create roadmaps and KPIs only to watch execution stall. And when reality pushes back, the assumption is that people aren’t trying hard enough.
In truth, most people want to do good work. If they aren’t, something’s making it difficult: broken tools, unclear goals, misaligned incentives, or systemic friction.
A Story from Education: Teachers and New Curriculum Mandates
A school district introduces a new curriculum with detailed plans and strict milestones to boost test scores. Months later, administrators notice some teachers are behind, skipping content, or improvising in ways that differ from the original plan.
The typical response is might be enforcement:
“Why aren’t you following the curriculum?”
But if dedicated teachers are struggling, a better question is:
“What’s getting in the way of teaching this effectively?”
When administrators ask this, real barriers emerge: the curriculum may be too rigid for diverse classrooms, students may have knowledge gaps, materials might arrive late, or teachers may lack sufficient training to fully grasp the new approach.
The issue isn’t a lack of commitment; it’s that the strategy didn’t reflect classroom realities. By asking the right questions, leaders discover true obstacles and enable real progress.
The Strategy Testing Loop
Instead of enforcing compliance immediately, we can test our strategy against real-world constraints.
- Observe: Where is the strategy failing to take root?
- Diagnose: What’s making execution difficult?
- Adapt: Remove friction, provide support, adjust direction
- Repeat: Strategy is dynamic. So is alignment.
This approach reframes resistance as insight. It’s about raising awareness of what the work actually requires.
Strategy as a Conversation: Unlocking Sustainable Progress
Let’s compare two approaches to the same issue:
- Compliance lens: “You’re not following the policy. Fix it.”
- Testing lens: “What’s getting in your way?”
Once barriers such as technical debt, brittle architecture, or unclear incentives surface, execution improves organically. When leaders treat resistance as information, they build trust and unlock progress without pressure.
Practical Steps to Begin
Start building a more adaptive, grounded approach to strategy execution:
- Try Wardley Mapping: Map a product or process with your team to spot misalignments early.
https://learnwardleymapping.com/introduction/ - Practice Systems Thinking: Ask, “What’s really going on here?” Look for patterns and connections.
https://thesystemsthinker.com/systems-thinking-what-why-when-where-and-how/ - Build Trust:Share your maps and insights. Invite critique. Encourage open dialogue and collaborative problem solving.
- Celebrate Progress: Recognize even small shifts. Change often scales when momentum builds.
Key Takeaways
- Resistance is often feedback, not a people problem.
- Use non-compliance as data, not a verdict.
- Remove blockers instead of pushing for alignment.
Bottom Line: Align strategy with ground truth
Strategy is real only when it survives contact with reality.
If a strategy doesn’t survive contact with real constraints, it’s not failing; it’s incomplete. The best leaders listen, adapt, and rework their strategies when teams struggle. Sustainable progress comes from asking better questions, not pushing harder.
To go beyond compliance, listen with understanding; often, we can learn what’s working and what’s possible.