On a recent flight, I watched a woman try to sneak an oversize briefcase and suitcase onto the plane. When challenged, she waved her boarding pass at the gate agent and declared, “Do you see what that says?” pointing to her top-tier status. “That means I get to do what I want.”
Her sense of entitlement was staggering, but familiar. Leaders of organizational transformation, such as major digital/data analytical capability overhauls, or launching a new set off offerings across the globe, often cling to equally delusional rationalizations. And just like that traveler, their self-justifications backfire.
The odds of transformation success are already dismal: 70% to 80% of efforts fail. While external forces can derail even the best-laid plans, more often it’s leaders’ self-inflicted fallacies that undo their own initiatives. I’ve identified five particularly destructive fallacies that appear again and again. Recognizing them is the first step. Choosing better responses is the only way through.
1. The Myth of the Mandate: Repeating Yesterday’s Wins
Justification: “I’ve done this before, and I was hired to do it again.”Reality: Past victories offer wisdom, not formulas.
Many leaders believe their résumé is a ready-made solution. They assume that because a strategy, campaign, or turnaround worked once, it should work again. A consumer-products executive I advised had saved a skincare brand with a precise campaign. When he joined a tech firm, he tried to cut-and-paste the same formula. The market, customer base, and competitors were different, and the approach failed miserably.
The danger of this fallacy is that it hides behind genuine strength. Leaders should use their experience, but if they impose it as a mandate, they miss the nuances of the new context. Teams sense the mismatch, and enthusiasm drains as people see yesterday’s playbook failing on today’s field.
The antidote: Treat mandates as invitations, not marching orders. Start by studying your new environment as if you were an anthropologist: walk the halls, ask questions, listen deeply. Instead of asking “What worked last time?” ask “What does this context demand?” Extract principles—such as how you built trust or navigated resistance—from your past, but resist the temptation to replicate recipes. That’s how you turn past wisdom into present credibility.
2. Excessive Tolerance: Making Change Optional
Justification: “I’m sure they’ll get on board eventually, we just need to give them time.”Reality: Some people have no intention of getting on board.
When leaders become exhausted, confrontation often feels harder than compromise. Deadlines slip, underperformers are excused, and resistance festers. Employees learn quickly that change is “recommended” but not required.
The costs are steep. Accountability erodes, peers resent double standards, and even those committed to change begin asking, “Why should I bother if others aren’t held to it?”
The antidote: Sharpen accountability and send clear, early signals. Use symbols—sometimes tough ones—to show that the “urgency of now” is real. Dashboards of metrics tracking progress and regressions are common. Sometimes removing long-tenured leaders whose behavior contradicts the change is necessary. When actions don’t match commitments, call it out. Consequences matter. Research on loss aversion shows that people fight harder to avoid losses than to gain bonuses. That means accountability must accompany rewards.
Yes, it will feel lonely. Yes, you may lose popularity. But credibility depends on consistency. Tolerance masquerades as empathy, but it undermines urgency. Leaders who name and enforce consequences create trust, because people know the rules apply to everyone.
3. Settling For Dysfunction: Accepting the Wrong Norms
Justification: “It is what it is. With time, people will come around.”Reality: Without sustained pressure, dysfunction becomes the new normal.
One COO I worked with entered his role determined to challenge entrenched practices. But when resistance persisted, his frustration grew. Eventually he lost his composure in a board meeting, mirroring the very volatility of the previous CEO he’d been hired to replace. Employees sighed, “At least with the old guy, we knew what to expect.” Instead of disrupting dysfunction, he had absorbed it.
This rationalization is subtle. Leaders begin doubting their instincts: Maybe it’s me. Maybe I’m asking too much. Surrounded by colleagues who shrug and say “Rome wasn’t built in a day,” leaders can slowly adopt resignation as their operating norm.
The antidote: Stay differentiated. Make time to decode the unhealthy patterns you see—why do meetings after the meeting carry more energy than the actual meeting? Why does feedback trigger overreaction? Then encode what should be true—optimism, accountability, or healthy debate—and measure progress against it. Even incremental wins reinforce hope and prevent you from being seduced into complacency.
Transformation requires leaders to behave differently than the culture they inherit. Settling into dysfunction might feel like relief, but it heralds surrender.
4. Dismissing the Devil You Know: Protecting the Wrong People
Justification: “She may not be perfect, but I can’t afford to lose her now. Better the devil you know.”Reality: The devil you know is still the devil.
Few decisions are harder than removing a long-tenured executive. Leaders justify delay by citing loyalty, sunk costs, or fear of disruption. But keeping misaligned leaders is corrosive. It demoralizes others, who see that performance doesn’t matter. It consumes disproportionate time and energy. And it erodes credibility, as people conclude the leader lacks the courage to act.
The antidote: Evict the devils. Not everyone should make the journey. Leaving someone in a role they cannot succeed in isn’t compassion, it’s cruelty. It sets them up for failure and broadcasts to everyone else that standards are optional.
Yes, exits are painful. But acute pain from a tough decision is far better than chronic pain from avoiding it. Free yourself to focus on people already predisposed to advance the vision. When you remove dams, momentum flows again.
5. Reporting Enmeshment: Confusing Emulation with Growth
Justification: “We’ve been a great team for years, and she’s now ready to succeed me.”Reality: Long-term reporting relationships often breed co-dependence, not development.
Mentoring is essential. But when a promising leader spends too long in one boss’s orbit, they risk becoming a replica rather than an original. I’ve seen organizations elevate successors who sound and act just like their predecessor, only to find that “more of the same” isn’t what transformation requires.
Enmeshment feels safe but creates blind spots. It can also choke off opportunities for broader growth. Without varied assignments, leaders stagnate, lacking the agility transformation demands.
The antidote: Move talent around, early and often. Diverse experiences stretch leaders’ styles and voices. Assign high-potentials to struggling business units, rival functions, or cross-border roles. The more of the organization they see, the stronger—and more authentic—they become. Emulation is admirable, but growth requires mobility.
Choosing the Path of Progress
Transformation isn’t undone by markets alone. More often, it’s these rationalizations, comforting stories leaders tell themselves, that derail progress. The woman at the airport thought her “special status” exempted her from the rules. Leaders often think the same.
But leaders who resist these fallacies, and instead choose accountability, contextual wisdom, differentiation, courage, and mobility, create transformations that last.
The costs of indulging rationalizations are dire: wasted time, lost credibility, and failed change. The benefits of escaping them are equally profound: resilient organizations, energized people, and futures worth building.
Don’t let the justifications win.
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