Focus Keyphrase: Overcoming Change Management Challenges

Why Change Management Fails—And What You Can Do About It

Leading transformation is tough. Even with a perfect plan, change initiatives often stall midway. At Pintail Solutions, we help organizations navigate the messy middle—where enthusiasm fades, resistance spikes, and momentum stalls. In this post, we explore real-world strategies for overcoming change management challenges and getting your transformation back on track.

The Cliff of Uncertainty: When Change Hits a Wall

Jason C. Bork, President of Pintail Solutions, recalls a large-scale pharma project that hit a standstill midway through rollout. Although the initial launch was strong—complete with communication, alignment, and support—momentum suddenly died. Sound familiar?

This moment, Bork explains, is the “change cliff”—when organizations metaphorically say: “Change is great… you go first.” Resistance kicks in. People retreat to old habits. Fear rises. Systems and leadership may even allow backsliding by not fully committing to the new way.

Why Resistance Happens (Even When Change Makes Sense)

• New behaviors are harder than old ones—especially during stressful times.
• Incentives and rewards haven’t shifted to match the change.
• Leaders allow legacy processes to run parallel to the new approach.

The bottom line: without proactive effort to reinforce new habits, people will revert to the path of least resistance. Culture always wins—unless you intentionally shape it.

“Burn the Boats”: Make the Old Way Inaccessible

To move forward, Bork references the story of Hernán Cortés: upon landing in the New World, he burned his ships to remove any option of retreat. Similarly, organizations must reduce access to the “old way” of doing things.

• Decommission outdated systems.
• Redirect project approvals through the new methodology only.
• Reward behaviors that support the new direction.

When teams see no path backward, they move forward by necessity—not convenience.

Turn Insight Into Action

Transformation success depends on getting people through that moment of doubt. By anticipating resistance, proactively eliminating legacy paths, and aligning behaviors to incentives, you can build sustainable change momentum.

Partner with Experts Who’ve Been There

At Pintail Solutions, we specialize in leading organizations through complex transformation. Whether you're rolling out new tech, revamping structures, or shifting culture, we’ll help you clear roadblocks before they derail your mission.

Explore more on how to structure a change management process.