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 biggest downside of remote work isn't lost productivity, but the elimination of serendipity. It removes the chance encounters that lead to friendships, mentorship, and cross-pollination of ideas. For those needing to build a network, the convenience of working from home comes at the high cost of isolation and stunted growth.
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.
While acknowledging the benefit of having mentors, Herb Wagner has found that the process of being a mentor is even more educational. Teaching and guiding others forces a deeper understanding of one's own principles and provides fresh perspectives from the next generation, offering greater personal and professional growth.
Individual self-help is often self-indulgent because we cannot see our own blind spots. True growth happens in a community context where relationships built on trust allow others to offer feedback. This makes the collective more intelligent than any individual working alone.
Instead of scheduling rigid, three-hour co-founder check-ins that often get canceled, adopt a 'counter-puncher' mindset. Keep important topics top-of-mind and seize spontaneous opportunities—like another meeting getting canceled—to have those crucial conversations. This fluid approach is more effective in a chaotic startup environment.
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.
Use the GROW model (Goal, Reality, Options, Way Forward) to structure coaching conversations. This simple set of question categories helps leaders guide their team members to find their own solutions, fostering independence and critical thinking without the leader needing to provide the answer directly.
Building influence requires a strategic approach. Actively survey your professional relationships, identify where you lack connections with stakeholders, and methodically invest time in building alliances with leaders who can advocate for your ideas when you're not in the room.
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.
The young founder hired an experienced executive who became a mentor and effectively his boss. He learned more from observing this leader's actions—how he interacted with people and approached problems—than from direct instruction. This demonstrates the power of learning through osmosis from seasoned operators.