A mentor isn't someone who provides step-by-step instructions. The most powerful learning comes from finding someone you admire and closely observing their every move, how they speak, and how they behave in the face of obstacles, rather than seeking direct guidance.

To build relationships with potential mentors or sponsors, replace the extractive ask of "Will you mentor me?" with the value-added offer of "How can I help you?". This non-transactional approach demonstrates your worth, builds genuine rapport, and makes influential people want to invest in your career.

Orlando Bravo argues valuable mentorship isn't found in occasional calls. It's cultivated through daily work with colleagues who have direct context on your challenges. Proximity allows for the deep, nuanced guidance that scheduled, low-context conversations cannot provide.

The pace of change in AI means even senior leaders must adopt a learner's mindset. Humility is teachability, and teachability is survivability. Successful leaders are willing to learn from junior colleagues, take basic courses, and admit they don't know everything, which is crucial when there is no established blueprint.

Don't wait for a promotion or new job opening to grow. Proactively identify other teams' pain points and offer your expertise to help solve them. This proactive helpfulness builds relationships, demonstrates your value across the organization, and organically opens doors to new skills and responsibilities.

Many leaders, particularly in technical fields, mistakenly believe their role is to provide all the answers. This approach disempowers teams and creates a bottleneck. Shifting from advising to coaching unlocks a team's problem-solving potential and allows leaders to scale their impact.

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.

For short-term mentoring to be impactful, it must be painful. The goal isn't gentle guidance but to make an overlooked opportunity or flaw so painfully obvious that the mentee is jolted into action, partly to prove the mentor wrong. It's 'crash therapy'—uncomfortable but highly effective at driving change.