The Courage to Disappoint: Why Real Leadership Requires Discomfort

Leadership is not a popularity contest. If everyone is consistently pleased with your decisions, you are more likely following the path of least resistance over actually exhibiting the action of leadership. Rather, true actions of leadership recognizes a fundamental truth: meaningful change requires disappointing people at a rate they can absorb.

Adaptive challenges demand that people give up something they value. Those might include cherished beliefs, familiar identities, comfortable ways of working, or long-held assumptions about how things should be. This loss creates disappointment, even grief. Leaders who try to shield people from this discomfort fail to create the conditions necessary for adaptation.

Consider what happens when leaders try to please everyone. They avoid naming the hard truths, the contradictions within their organizations - aka the gap between espoused values and actual behavior. They provide technical fixes to adaptive problems, offering quick solutions that don't require people to change themselves. This is not leadership: it is conflict avoidance disguised as harmony.

Disappointing people at a rate they can handle is the critical balance. It acknowledges that adaptive work is painful. People must reexamine loyalties, question competencies they've spent years developing, and let go of interpretations and assumptions that have long given their work meaning. If you push too hard, people will retreat into denial or rebellion. If you push too gently, the necessary learning never occurs.

This does not mean being callous or deliberately stepping on toes to accomplish this. Rather, it means holding people accountable to their own highest aspirations even when they resist. It means surfacing the conflicts people would rather avoid. It means asking questions that make people uncomfortable because those questions expose the adaptive work that must be done.

It also does not means walking on eggshells around people, and being perpetually worried about stepping on toes. This robs their organizations of the friction necessary for growth. They collude in comfortable fictions rather than name uncomfortable realities. Their teams stay stuck, not because people lack capacity, but because no one is willing to disturb the equilibrium that keeps everyone safe but stagnant.

If no one is disappointed with you, ask yourself: What difficult reality am I not naming? What conflict am I smoothing over prematurely? What loss am I pretending people don't need to face? The absence of dissatisfaction often signals that the adaptive work isn't happening.

True leadership requires embracing this paradox: you must care deeply about people while simultaneously refusing to protect them from the disorienting work of change. You must create enough disequilibrium to mobilize people without overwhelming their capacity to adapt. The goal isn't to disappoint for disappointment's sake, but to recognize that disappointment signals the presence of the necessary learning for meaningful change.