The "memo is the strategy" isn't just a CEO problem. Teams often run the same play, creating roadmaps, OKRs, or retro actions that serve as announcements of intent but lack any real execution or follow-through mechanism.

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.

Expert product leadership is not about mastering standard frameworks, but about discerning which elements apply to a company's unique situation. In many contexts, like a PE-backed manufacturer going digital, most textbook frameworks are unsuitable and must be selectively combined, adapted, or rejected entirely to be effective.

For startups tackling monumental challenges, complex planning frameworks like OKRs are a distraction. Instead, maintain a clear, ambitious long-term vision and focus the entire company's energy on executing the immediate next step with maximum speed and quality.

When evaluating others' success, ask if their strategy would work for most people who adopt it, or if it relied heavily on luck. If a strategy isn't reproducible and leaves many casualties behind, it's not a model to be learned from, regardless of the impressive outlier outcome.

Principles from companies like Amazon cannot be simply copy-pasted. Success requires adapting the "right tool for the job" and recognizing that culture eats strategy. Without the right incentives, data quality, and low-politics environment, these frameworks are destined to fail.

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.

A common OKR failure is assigning teams high-level business metrics (like ARR) which they can only contribute to, not directly influence. Success requires focusing on influenceable customer behaviors while demonstrating how they correlate to the company's broader contribution-level goals.

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.