Recovering Judgment in an Age of Easy Wisdom

By Federico Malatesta 

Years ago, I presented a post-project appraisal to a board that included former politicians and successful businessmen. The appraisal was direct: the project had not gone well. When I finished outlining the failure points, the room went quiet. The CEO looked at me and asked, “So you’re saying we need to be tougher and smarter?” For a moment, I assumed I would be shown the door. Instead, after a long pause, he nodded and said, “You’re right. We didn’t get this one right.”

There was no defensiveness, no pivot to a softer frame. Just acknowledgment and the expectation that we would understand the failure rather than bury it. That moment taught me what judgment looks like in practice, and how rare it has become.

The Problem with “Leadership Wisdom”

Contemporary leadership discourse has developed a particular weakness: the preference for attitudes over analysis. The concepts that circulate most widely – authenticity, empowerment, presence, vulnerability – have become interchangeable virtues. They sound correct because they follow the familiar shape of insight, not because they clarify what a situation actually demands.

The philosopher Slavoj Žižek once demonstrated this by offering four contradictory statements about life (I’m paraphrasing here): “reject immediacy for eternity; reject eternity for the present; find eternity in fleeting moments; accept the tension between them.” Each sounds wise. All contradict each other. The structure does the work, so we end up nodding before thinking.

Leadership advice often operates the same way. When a team underperforms, a leader can call for “more empowerment.” If empowerment produces confusion, they pivot to “clearer direction.” If direction appears rigid, they shift to “authentic leadership.” Each rotation feels justified. Each one bypasses the harder work of diagnosing what the situation actually requires.

The result is conceptual mobility without real commitment and responsibility that migrates elsewhere, often to consultants who provide cover for decisions leadership prefers not to own directly.

A Different Orientation

Wisdom, in its older sense, meant the capacity to evaluate competing obligations, recognize constraints, and choose despite imperfect coherence. It wasn’t a harmonizing technique but a disciplined confrontation with trade-offs. Leadership requires the same discipline: interpreting ambiguity, identifying which priorities must prevail, and accepting the consequences of that choice. We need to recover what leadership has always required before we buried it under abstractions.

Three Practices for Restoring Judgment

1. Diagnose before you declare a stance on a difficult decision. Write down what you actually know versus what approach you’re tempted to adopt. If you can’t articulate the specific complexity of the situation, it is likely that you are not ready to lead through it. The discipline is simple: facts first, framing second.

2. Use expertise as a resource, not a shield. When you bring in external consultants, define upfront which decisions remain yours. If you find yourself saying “the analysis showed…” to justify an unpopular call, ask whether you’re explaining your reasoning or hiding from your direct responsibility. External validation can be helpful, but it should not be relied on indefinitely.

3. Name what you own. Identify one decision you’ve recently attributed to circumstances, timing, or organizational constraints that was actually yours to make. Say it out loud, to yourself or to your team. Responsibility that is not owned tends to stay unexercised. The CEO in that boardroom didn’t qualify his acknowledgment. He didn’t find a scapegoat. That’s what being accountable sounds like.

Judgment strengthens through use. It is restored not by consuming more insight, but by practicing discernment in concrete situations, where trade-offs are real and consequences cannot be outsourced. The difference between gestures that resemble understanding and practices that embody it becomes visible only when leaders slow down enough to diagnose, choose, and stand behind their choices. In that sense, judgment is not a trait to be rediscovered, but a capacity to be exercised, deliberately, repeatedly, and in public.

Author Bio: Federico Malatesta is the founder of FM Transformational Coaching™, a practice that unites executive insight, leadership frameworks, and lived experience to explore how identity evolves through change. Previously Chief Investment Officer for a $40 billion energy portfolio, Federico now applies the discipline of global finance to the psychology of transformation.

Federico operates from the Artha Ranch in Texas, where he breeds and raises reined cow horses. He writes regularly on narrative collapse, identity, and leadership transitions.