When new leadership arrives, a long-serving executive's value lies in their deep institutional knowledge and cross-functional relationships. They can act as a crucial bridge, helping synthesize diverse perspectives to guide the new team's vision and ensure a smoother transition.

It is significantly more difficult to step in as a non-founder CEO than to build a business from scratch. The new leader must contend with inherited business inertia, a pre-existing culture shaped by the founder, and constant comparisons, making transformative change much harder.

When an executive leaves, the CEO should step in to run their department directly. This provides invaluable operational context for hiring a replacement and empowers the CEO to make necessary but difficult changes (org structure, personnel) that a new hire would hesitate to implement.

The complexity of long-term estate and succession planning often leads to indefinite postponement. A more effective approach is to create a plan based on the business's current state and set a recurring calendar reminder to review and update it every two years.

When planning for the business's future without you, prioritize the stability and job security of your team. Confident and secure employees are the best guarantee that your clients will be taken care of, creating a more resilient and sustainable legacy.

The transition from a hands-on contributor to a leader is one of the hardest professional shifts. It requires consciously moving away from execution by learning to trust and delegate. This is achieved by hiring talented people and then empowering them to operate, even if it means simply getting out of their way.

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.

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.

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.