All founders make high-impact mistakes. The critical failure point is when those mistakes erode their confidence, leading to hesitation. This indecisiveness creates a power vacuum, causing senior employees to get nervous and jockey for position, which spirals the organization into a dysfunctional, political state.

Unlike startups, institutions like CPPIB that must endure for 75+ years need to be the "exact opposite of a founder culture." The focus is on institutionalizing processes so the organization operates independently of any single individual, ensuring stability and succession over many generations of leadership.

Even with full board support, a successor CEO may lack the intrinsic 'moral authority' to make drastic 'burn the boats' decisions. This courage is harder to summon without the deep-seated capital a founder naturally possesses, making company-altering transformation more challenging for an outsider.

Instead of starting from a textbook, WCM developed its effective culture by identifying the negative traits of its original founder's regime—control, opacity, and stinginess—and deliberately doing the opposite. This 'inversion' method provides a powerful, practical template for cultural transformation.

Successor CEOs cannot replicate the founder's all-encompassing "working memory" of the company and its products. Recognizing this is key. The role must shift from knowing everything to building a cohesive team and focusing on the few strategic decisions only the CEO can make.

The founder hired an experienced CEO and then rotated through leadership roles in different departments (brand, product, tech). This created a self-designed, high-stakes apprenticeship, allowing him to learn every facet of the business from experts before confidently retaking the CEO role.

When transitioning leadership, you must allow your successors to make mistakes. True learning comes from fixing failures, not just replicating successes. As the founder, your instinct is to prevent errors, but you must permit 'fuck ups' for the next generation to truly develop their own capabilities and own the business.

Founders remain long after hired executives depart, inheriting the outcomes of past choices. This long-term ownership is a powerful justification for founders to stay deeply involved in key decisions, trusting their unique context over an expert's resume.