Document Expectations Instead of Yelling

Ben Horowitz believes the most destructive leadership mistake is hesitation. When faced with two bad options, leaders must still make a clear choice rather than avoid the decision entirely. The psychological muscle required for great leadership is the ability to "click in the abyss" and choose the slightly better path, even when both options appear terrible.

The hardest decisions are precisely where leaders add their unique value. As Horowitz explains, "If everybody agrees with the decision, then you didn't add any value because they would have done that without you. So the only value you ever add is when you make a decision that most people don't like." This perspective reframes unpopular decisions as evidence of leadership rather than failure.

Leaders must develop comfort with imperfection. The "CEO test" has a median score of 18, not 90 - meaning even successful leaders regularly earn D-minuses. What matters is avoiding the complete failure (the F) while continuing to move forward. This is why Horowitz believes C-minus students often make better CEOs than straight-A students; they're already comfortable with imperfection and failure.

Confidence is the critical foundation for leadership effectiveness. When leaders lose confidence after making mistakes, they begin to hesitate on subsequent decisions. This hesitation creates a dangerous vacuum where senior team members feel compelled to jump in and make decisions, leading to political dysfunction. The most valuable support for CEOs is helping them maintain confidence through inevitable failures.

For product managers specifically, Horowitz emphasizes that their role is fundamentally about leadership through influence. The job isn't about completing tasks like writing specs or conducting interviews - it's about delivering a product that customers love and outperforms competitors. This requires getting engineering to understand you with clarity, understanding engineering with clarity, and having a strong view of the market and technology landscape.

When evaluating talent, Horowitz recommends focusing on strengths rather than absence of weaknesses. The question should be: "Do they have a world-class strength?" rather than fixating on flaws. This applies to both hiring and investment decisions. As he puts it, "You don't judge a person by the worst thing that ever happened to them... you want to judge people on what they do well, not what they screwed up."

Leaders should aim to be respected in the long run rather than liked in the short term. The most important things you'll say to people are often things they don't want to hear, but these difficult truths can save companies and careers. This requires the courage to run toward fear rather than away from it.

Leadership Implications

For leaders making difficult decisions:

• When facing two bad options, recognize that hesitation is worse than either choice
• Explicitly acknowledge the downsides of your decision rather than pretending there aren't any
• Remember that unpopular decisions are where you add unique value as a leader

For managing your psychology:

• Build confidence through small wins that lead to the next small win
• Recognize that your internal beliefs about yourself have more impact than external circumstances
• Accept that the leadership "test" has a low median score - perfection isn't the goal

For developing teams:

• As CEO, focus on finding great people rather than developing mediocre ones
• Look for "managerial leverage" - people who bring ideas to you rather than waiting for direction
• Judge people on their strengths and potential, not their worst moments or weaknesses

For product managers:

• Focus on leadership through influence rather than task completion
• Your job is delivering winning products, not checking boxes
• Develop clarity in both expressing your vision and understanding technical realities