To combat founder stagnation, Kavak's CEO undertakes a rigorous annual exercise of "firing" himself. He defines the ideal CEO profile for the company's next phase and then objectively assesses if he can evolve by letting go of old habits and personas to fulfill that role.
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As part of their annual strategy refresh, a top CEO leads her team in a "blank sheet" exercise: designing a new company from scratch to compete with them. This proactive self-disruption forces them to identify their own weaknesses and market gaps, generating fresh ideas to incorporate into their actual business strategy.
Despite success, founder Kevin Wagstaff felt like an "imposter" as the company scaled beyond $10M ARR. He recognized his strengths were in the early, scrappy "bias to action" phase, not managing a larger organization. He proactively brought in a seasoned CEO better suited for the next stage of growth.
Harvey CEO Winston Weinberg experiences a four-month cycle of accumulating pressure from unsolved problems. He argues the only release is a fundamental reinvention: making a new leadership hire, restructuring the company, or cutting a failing initiative. This cycle is necessary to unlock the next stage of scale.
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.
After eight years of grinding, the founder recognized he had taken the company as far as his skillset allowed. Instead of clinging to control, he proactively sought an external CEO with the business acumen he lacked, viewing the hire as a "life preserver" to rocket-ship the company's growth.
A top-performing CEO adapted the board practice of an "executive session." He periodically removes himself from his own leadership meetings and asks an HR leader to gather candid feedback on his performance. This powerfully models vulnerability and a commitment to continuous improvement for the entire organization.
To avoid complacency, Miro's CEO asks himself daily, "If I started this company today, what would the product and strategy look like?" The answer to this question determines whether the company needs a small evolution or a complete strategic rebuild to stay relevant in the market.
Borrowing a quote from Shopify's CEO, Mike Cannon-Brookes emphasizes that a founder's key responsibility is to counteract the natural decline in ambition that occurs as a company grows. They must constantly push the organization to remain bold and hungry.
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.
The M&A Science founder stepped back as CEO from his scaling software company, Dealroom, because his strength is in the early "boots on the ground" phase, not optimization and process maturity. This highlights the importance for founders to align their role with their core strengths rather than clinging to a title.
