OKRs and SMART goals are repackaged versions of Peter Drucker's 1940s "Management by Objectives." This framework was designed for simple, repetitive tasks on an assembly line, making it fundamentally unsuited for today's complex, knowledge-based work where problems have no single right solution.

Cascading OKRs through multiple layers (company to department to team to individual) often results in "OKR theater" where the connection to business impact is lost. Instead, an individual product manager's goals should be no more than one link away from a core business objective that leadership cares about.

For goal-setting to be effective, limit company-wide goals to three. Designate one goal as the ultimate tie-breaker in resource conflicts. Ensure goals are simple enough for an intern to understand. Crucially, your strategy must involve painful trade-offs ('strategy should hurt'), otherwise you haven't truly prioritized.

A common leadership mistake is setting impossible goals. This often stems from a flawed planning process that doesn't clearly distinguish between aspirational "stretch" goals and committed "planned" goals. Without this clarity, especially in financial planning, teams are set up for failure.

Simply stating a goal, like "increase sales by 15%," is insufficient for autonomous teams. Leaders must also articulate the "anti-vision"—the negative outcomes to avoid, such as eroding customer experience. This rich context provides clearer guardrails and a more nuanced understanding of the mission.

Vague goals like "get better" lack emotional weight. Creating precise, detailed goals—like "add 50 qualified opportunities by March 31st"—fosters a strong psychological and emotional connection to the outcome. This attachment is crucial for maintaining motivation and overcoming obstacles.

Setting rigid targets incentivizes employees to present favorable numbers, even subconsciously. This "performance theater" discourages them from investigating negative results, which are often the source of valuable learning. The muscle for detective work atrophies, and real problems remain hidden beneath good-looking metrics.

The culture around OKRs often treats the framework as gospel. When teams struggle, the default response is "you're doing them wrong," labeling critics as heretics. This prevents genuine discussion about whether the system is fundamentally flawed, trapping organizations in a cycle of failed implementation.

The most successful sales teams don't necessarily hit every specific goal they write down. Instead, their success comes from the continuous habit of setting goals. This constant process of intentionality leads to significant overall improvement and achievements they didn't even initially plan for.