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.

Effective leadership transitions must be planned years in advance. The successor should gradually assume managerial duties, making the final handover a natural, expected event for employees and LPs. Rushed plans fail, especially if the departing leader isn't truly ready to retire.

Instead of abrupt changes, Sequoia employs a gradual, multi-year transition process for its leadership stewards. Past leaders like Michael Moritz and Doug Leone remained involved for years after handing over the reins, ensuring stability and continuity for the firm and its LPs.

To ensure a smooth leadership handover, John Zimmer transitioned from an operating role to a board seat before fully departing Lyft. This deliberate, two-year process provided stability and support for the company's new leadership team during its next chapter.

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.

Successful delegation is not an abrupt handoff but a gradual process. Bring in a senior person and collaborate with them, then slowly cede specific responsibilities (e.g., customer interviews). This allows you to transition your own role from day-to-day operator to an internal advisor, ensuring continuity.

To transition from founder to CEO, Unbound Merino's co-founder admitted his own uncertainty and directly asked his top executive what she needed from him to consider him a great CEO. This act of vulnerability built trust and provided a clear path for his leadership development.