Resisting the Escalation Trap
Separating Smart Persistence from Stubborn Commitment
Issue 223, July 31, 2025
How do you balance what you think your customers need versus what they want? Let’s say you are ahead of the trend curve in your industry, and are launching an event that is so forward-thinking that it challenges current status quo thinking. Here’s a real-life example. In the past, a marketing director produced an event for CFOs on sustainability initiatives and cost-savings and how they should be factored into the balance sheet, not as an expense, but as an asset. This was well before the mainstream was thinking about the sustainability impact. Or a marketing team organized a conference on user-generated content when die-hard legacy editors and professional writers believed they were the sole source of written content. In other words, the organizers envisioned a future so clearly and were so convinced about the transformation their industry was about to undergo that by force of conviction, they developed an event to help decision makers anticipate the changes. But guess what, hardly anyone registered for the event and those who attended were resistant to the new ideas or completely missed the point.
What did the marketers do? They went ahead and planned year two of the events, doubling down on more resources and larger budgets. What’s going on here? Did passion and personal bias force these decisions? These marketers aren’t alone. It is a pattern that extends far beyond failed conferences. Across industries and organizations, smart leaders find themselves trapped in the same destructive cycle, particularly when the chips are down, markets gyrate, or competitors seem to be eating an organization for lunch.
The cycle is an escalation trap, a deeply human tendency to double down on bad decisions in the hope that renewed commitment will eventually turn failure into success.
The Psychology Behind Doubling Down
Let’s bring it up a notch. Think of your own experience. A high-stakes initiative starts with enthusiasm, only to quietly fall short of expectations. Yet instead of pausing to recalibrate, we push harder. More budget. More staff. More time. The problem isn’t a lack of effort. Reality check: Rarely does such enthusiasm turn into success. Why?
The escalation trap is not uncommon. In an insular organizational culture, there is a powerful undercurrent of ego, institutional inertia, and the uncomfortable truth that smart people can be blind to their own influence. At 2040, we help clients confront that truth and work with leaders to build systems that make mid-course corrections a sign of strength, not weakness. We explore why we stick with bad decisions.
We have identified blind spots in even the most well-intentioned change initiatives. We have cautioned about the risks of poor decision-making including, Mastering the Art of Decision-Making in Uncertain Times, but the escalation trap focuses on the micro-failure of decision logic. The trap also reveals hidden power dynamics (Who’s Really Making the Decisions?) when escalation is often sustained by those too powerful to be questioned. We also caution clients about the misinterpretations of data (Data, Data Everywhere) and the fact that the escalation trap adds another distortion when the data says stop, but the ego says ‘go.’
Why We Double Down
Understanding the escalation trap is complex and often organization-specific. Psychology plays a role (doesn’t it always) in blurring the lines of rational decision making and personal bias. One underlying psychological motivation is that personal identity becomes fused with the initiative. The commitment becomes ego-driven, often to protect and preserve one’s image. That force of personality can override logic and common sense. How is that possible? It’s an outcome of dysfunctional leadership and poorly designed organizational governance frameworks that enable and reinforce the continuation of a poorly performing project. Some would call it a personal passion project, but honestly, what does it have to do with customers? It has more to do with ego, or worse, hubris.
Psychological breakdowns can be pervasive. Backing down from a bad idea is resisted by fear of appearing indecisive or incompetent. A team may not push back, fearing the power of management. Think about the cliche of the tech bro culture; there is an embedded hero narrative where tenacity is celebrated even if it’s misapplied. In this type of misaligned culture, teams rarely see what they’re sacrificing by sticking with a bad idea. They are dazzled by a superhero leader.
And there’s even more to it psychologically. The champions of a failing project defend the decision with the refrain, “Just a little more time/money will fix it.” Repressed critics are shut out of feedback loops, and chances are, no one is asking, ‘What are we learning from this?’ To exacerbate the situation, the organization isn’t measuring what matters. Internal reviews may focus on effort and initiative inputs, not outcomes — results.
The startup operating philosophy of ‘innovate, move fast and break it’ has been adapted by many established organizations without the structure to manage the process. As a result, the escalation trap can become fatal to the bottom line. Understanding these psychological drivers is crucial but recognizing them in real-time requires knowing what to look for. The escalation trap rarely announces itself—it creeps in gradually, disguised as determination and strategic persistence.
Warning Signs: Recognizing the Trap Before It’s Too Late
Smart leaders learn to spot the escalation commitment trap before it consumes valuable resources. Watch for these red flags in your organization:
- Language Patterns: When project updates consistently focus on effort rather than results (“We’re working really hard on this”) or when you hear phrases like “We just need a little more time” repeatedly, the trap may already be triggered. Similarly, when team members stop asking critical questions or challenging assumptions, groupthink has likely taken hold.
- Meeting Dynamics: Pay attention to who speaks and who stays silent in project reviews. If dissenting voices are marginalized or if the same champion always dominates discussions about troubled initiatives, healthy debate has been stifled. Meetings that focus primarily on what’s been done rather than what’s been learned signal dangerous tunnel vision.
- Metrics Manipulation: Teams caught in the escalation trap often redefine success metrics midstream to avoid admitting failure. If you notice goalposts moving or hear explanations for why traditional success measures “don’t apply” to this particular project, exercise caution.
- Resource Allocation Patterns: When failing projects consistently receive additional resources while successful initiatives are starved for support, organizational priorities have become inverted. This often happens when powerful sponsors protect their pet projects at the expense of the overall organizational portfolio performance.
- Emotional Investment: The strongest warning sign is when project discussions become emotionally charged rather than analytically driven. If questioning the project feels like a personal attack on its champion, identity has become dangerously fused with the initiative.
Recognizing these warning signs is only the first step. The real challenge lies in building organizational systems that prevent the escalation trap from taking hold in the first place—or breaking free when you’re already caught in its grip.
Breaking Free: A Systematic Approach to Course Correction
Awareness is the first step toward meaningful change. Once you recognize the warning signs, the next challenge is building organizational systems that make a course correction feel natural rather than threatening. This requires a holistic approach that addresses culture, governance, and decision-making processes. The goal isn’t to become risk-averse or abandon bold thinking. Instead, it’s about creating an environment where intelligent persistence can be distinguished from stubborn commitment to bad ideas. Here’s how leading organizations build that capability:
- Reframe: From Success/Failure to Learning/Growth
The most powerful antidote to the escalation trap is cultural: shifting from a binary success/failure mindset to one focused on learning and growth. This isn’t just semantics—it fundamentally changes how teams approach risk and evaluate outcomes.
Implement the approach by establishing “learning reviews” alongside traditional performance reviews. Instead of asking “Did we hit our targets?” also ask “What did we discover that we didn’t expect?” and “How has this changed our understanding of our customers or market?” When teams know they’ll be evaluated partly on insights not just metrics, they become more willing to acknowledge when an approach isn’t working.
- Identify Assumptions: The Reverse Premortem
Before launching any high-risk initiative, conduct a “reverse premortem”—imagine the project has failed spectacularly and work backwards to identify what went wrong. This exercise, popularized by psychologist Gary Klein, forces teams to confront their blind spots while enthusiasm is still high, but commitment isn’t yet entrenched.
Netflix famously used this approach when launching their streaming service. They didn’t just plan for success; they systematically identified what could kill the initiative: bandwidth limitations, content licensing challenges, and consumer adoption resistance. By naming these risks upfront, they created mitigation strategies and clear triggers for when to pivot.
Structure your reverse premortem by asking: What are the top five reasons this project could fail? What assumptions are we making about customer behavior, market conditions, or our own capabilities? Which of these assumptions are most critical and least tested? Then build learning experiments specifically designed to test your riskiest assumptions early and cheaply.
- Create Pause Points: The Governance Safety Net
Redesign your portfolio or project governance framework to require formal reassessment at predetermined milestones, not just during budget reviews, but based on fundamental strategy questions. These pause points serve as organizational circuit breakers, preventing projects from building unstoppable momentum.
Amazon’s two-way door decision framework exemplifies this thinking. For reversible decisions (one-way doors), they move fast and accept mistakes. But for irreversible decisions (two-way doors), they build in multiple checkpoints and require broader consensus. Each checkpoint asks not just “Are we on track?” but “Do we still believe this is the right door to walk through?”
Effective pause points include specific trigger questions: Has our understanding of the customer problem changed? Are our core assumptions still valid? What have we learned that suggests we should adjust course? Most importantly, create psychological safety around these discussions by celebrating teams that identify the need for course corrections early.
- De-Shame Pivoting: Redefining Organizational Narratives
Perhaps the most crucial intervention is cultural: reframing pivots and strategic withdrawals as signs of organizational intelligence rather than failure. This requires deliberate narrative management from leadership.
Consider how Slack emerged from a pivot. Stewart Butterfield’s team was building a gaming platform called Glitch when they realized their internal communication tool was more valuable than the game itself. Instead of doubling down on the gaming they’d already invested in for years, they celebrated the insights that led them to messaging. Today, Slack’s origin story is told as a triumph of strategic agility, not a gaming failure.
Build this mindset by creating recognition across the organization when teams make smart strategic redirections. Publicly recognize the courage that was required to change course and the insights that enabled the shift. Maintain a “lessons learned” database that captures valuable insights from both successful and redirected initiatives, demonstrating that organizational learning has tangible value.
- The Objective Mediator: Removing Politics from Decisions
Sanofi’s approach of using AI agents to provide objective project assessments represents a fascinating evolution in governance. According to CEO Paul Hudson, they start many committee meetings with an AI agent’s recommendation on whether to proceed with a project. The agent has no career stake, no emotional investment, and no fear of political consequences.
While AI mediation isn’t feasible for every organization, the principle is broadly applicable: introduce objective voices into decision processes. This might mean rotating external advisors into project reviews, creating anonymous feedback channels, or establishing devil’s advocate roles that rotate among team members.
One pharmaceutical company assigns a “red team” to every major initiative—a group specifically tasked with identifying flaws and challenging assumptions. The red team reports directly to the C-suite, insulating them from project politics. Their mandate isn’t to be negative but to ensure that someone is always asking the hard questions.
The key is structural: Create mechanisms that reward honest assessment over loyalty to failing initiatives. When objective analysis has a clear voice in decision-making, the escalation trap becomes much harder to fall into.
The Path Forward
Escaping the escalation trap isn’t about becoming risk-averse or abandoning bold initiatives. It’s about building organizational wisdom—the ability to distinguish between intelligent persistence and stubborn commitment to bad ideas. The companies that master this balance don’t just avoid costly mistakes; they create cultures where innovation thrives because people feel safe to experiment, learn, and course correct. This isn’t easy; the human factor is and can be an incredible force, both positive and negative. That force, like avoiding the escalation trap, requires commitment, takes energy and willingness to admit challenges and most importantly, embracing letting go.
The question isn’t whether your organization will face projects that should be redirected or abandoned. The question is whether you’ll recognize them in time to turn potential failures into valuable learning experiences.
The Truth About Transformation: Why Most Change Initiatives Fail (And How Yours Can Succeed)
Why do 70% of organizational transformations fail?
The brutal truth: It’s not about strategy, technology, or resources. Organizations fail because they fundamentally misunderstand what drives change—the human factor.
While leaders obsess over digital tools, process improvements, and operational efficiency, they’re missing the most critical element: the psychological, behavioral, and cultural dynamics that actually determine whether transformation takes hold or crashes and burns.
The 2040 Framework reveals what really works:
- Why your workforce unconsciously sabotages change (and how to prevent it)
- The hidden biases that derail even the best-laid transformation plans
- How to build psychological safety that accelerates rather than impedes progress
- The difference between performative change and transformative change that sticks
This isn’t theory—it’s a battle-tested playbook. We’ve compiled real-world insights from organizations of all sizes, revealing the elements that comprise genuine change. Through provocative case studies, you’ll see exactly how transformations derail—and more importantly, how to ensure yours doesn’t.
What makes this different: While most change management books focus on process and tools, The Truth About Transformation tackles the messy, complex, utterly human reality of organizational change. You’ll discover why honoring, respecting, and acknowledging the human factor isn’t just nice—it’s the difference between transformation and expensive reorganization.
Perfect for: CEOs, change leaders, consultants, and anyone tired of watching transformation initiatives fizzle out despite massive investment.
Now available in paperback—because real transformation requires real understanding.
Ready to stop failing at change? Your organization’s future depends on getting this right.
