Everyone knew the emperor was naked. But no one dared say a word.
That’s the tension of a Catch-22: the truth is visible, even obvious, but saying it carries risk. Ministers feared humiliation. Townspeople feared reprisal. The emperor couldn’t admit it without losing legitimacy. Only a child, innocent, uninvolved, unafraid, and therefore uniquely free, could say what others dared not voice.
In leadership, the hardest truths are often the ones no one feels safe to say.
Catch-22s are among the most dangerous traps in organizational life. You see the problem, but naming it can make you appear disgruntled, disloyal, or self-serving. Proposing a solution invites resistance. Staying silent preserves dysfunction.
This is why companies often hire expensive consultants only to be told, in polished PowerPoint, what employees have known for years. Internal critiques feel political. Suggestions from peers can be dismissed as ambition in disguise. But a McKinsey partner can say what a manager cannot – not because it’s more insightful, but because it’s less political.
When IBM was struggling in the early 1990s, executives understood the problems – siloes, bureaucracy, and irrelevance – but saying so was political suicide. It took Lou Gerstner, an outsider with no tech background. He had nothing to protect and no alliances to defend. He said the obvious. He didn’t invent new solutions; he supported existing ones. His neutrality gave him the authority others lacked.
The same happened at Ford in 2006. The company was floundering. Insiders saw it, but speaking up could end a career. Then Alan Mulally arrived from Boeing without any Detroit loyalties. He asked blunt questions, demanded honesty, and addressed the elephants in the room that others couldn’t. He wasn’t necessarily smarter, he was just freer.
These are classic Catch-22s: speak up and pay the price or stay silent and enable failure. In such moments what organizations need isn’t just better ideas, they need better messengers. Outsiders with no agenda. Someone who can say what others can’t.
This isn’t a new insight. The Torah saw it long ago.
In Parshas Yisro, Moshe is overwhelmed by his duties to lead, judge, and manage. People were lining up from dawn to dusk. It was unsustainable. Yet no elder dares suggest delegation. It would seem disloyal, arrogant or insubordinate. Only Yitro, Moshe’s father-in-law and a Midianite priest, can intervene: “What you are doing is not good.” He proposes a structure of delegation. Moshe accepts. Yitro’s distance gave him credibility. His voice carried no subtext, only concern.
In this week’s parsha, Pinchas, a more explosive crisis unfolds. Zimri, a tribal prince, openly defies Moshe, bringing a Midianite woman, Kozbi, into his tent – a provocative act amid national moral collapse. Moshe is silent. Chazal explain that Zimri challenged him directly: “If this is forbidden, who permitted you to marry the daughter of Yisro?” – a pointed reference to Tziporah, Moshe’s Midianite wife. Though Moshe’s case was clearly different, the confrontation rendered Moshe powerless. Any response could be dismissed as personal defense.
Pinchas steps in. He too has reason to take offense. Chazal say his mother was Tziporah’s sister, also a Midianite. The challenge to Moshe was, in a sense, also a challenge to his own family and his legitimacy. But unlike Moshe, Pinchas had not been publicly confronted. He could act without appearing defensive. He was better positioned to respond.
And he does, confronting the crisis and restoring order. The Torah praises his zeal. What made him effective wasn’t detachment. It was the perception of detachment. He acted not because he was above the issue, but because he wasn’t the one being attacked.
This dynamic plays out in families and education. A parent or teacher may offer guidance for years with little visible impact. Then a child returns from a summer in NCSY Kollel or a year in yeshiva transformed, nott because the message changed, but because the setting did. At home, listening to a parent feels like conceding. Among peers, religious growth may feel uncool. But in a new setting, the Catch-22 dissolves. There’s no ego or past to defend. The message can finally be heard.
That’s why people turn to therapists, rabbanim, or mentors – not always for new insight, but for the permission to accept what they already know. To make conscious what the subconscious has already internalized. A couple may recognize their issues but fear speaking them aloud. An outsider gives voice to the unspoken.
Often, we already know the truth. What we lack is the freedom to say it, or to hear it without shame. That’s why we need others, not to enlighten us, but to unburden us.
This reveals something essential about leadership: seeing the path forward doesn’t always mean you’re the one to lead the charge. Authority doesn’t guarantee agency. Proximity can paralyze. Sometimes, the most effective move is to step aside so that someone else, better positioned, can speak.
Delegating the message isn’t weakness. It’s strategy. It’s humility. It’s love. When the goal is resolution, not recognition, the messenger may matter more than the message.
This is the shift leadership coach Dan Sullivan calls moving from how to who. Leadership isn’t always about solving the problem yourself, it’s about identifying who can. Escaping a Catch-22 is rarely about invention. It’s about orchestration – not how do I solve this, but who can act where I should not.
At its core, leadership is the art of enabling others. And at times, that means choosing silence, not from fear, but from wisdom, so that another voice can rise and be heard.
