Rachel Lockett

Rachel Lockett spent years as a senior HR leader at Pinterest and Stripe before becoming an executive coach working with CEOs, founders, and tech leaders -- giving her both the operator perspective and the coaching expertise to bridge theory and practice. Their core argument: Coaching unlocks brilliance and builds compounding team capability. Directing trains dependency and creates bottlenecks. The evidence is specific: An AI company CEO ('Jeff') who was the blocker on every product and business decision, coaching helped him create squads with clear KPIs, shift from deciding everything to asking good questions -- within weeks the teams moved faster and he freed time for vision and strategy. Furthermore, the Harvard Business Review 'monkey on the back' concept: leaders must keep the monkey on the report's back rather than taking every problem onto their own. In Rachel Lockett's own words: "Most leaders, especially technical leaders, assume they have to have all the answers. People have climbed the ladder because they've been dependable, reliable, the smartest person in the room. But great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way. It's an alternative path that unlocks brilliance in your team and is way more motivating for the people around you." (Explaining why coaching beats directing for team capability at scale.)

Executive coach and former longtime HR leader at Pinterest and Stripe; works with CEOs, founders, and leaders at tech companies on resilience, emotional intelligence, and building trusted teams Their core argument: Coaching creates the psychological safety that enables honest conversations -- start with curiosity, not directives. The evidence is specific: Live coaching demo with Lenny on the podcast -- asking 'What is it like to be a dad?' and reflecting back emotions in under 60 seconds. Furthermore, the GROW model applied in real-time: Goal, Reality, Options, Way forward. In Rachel Lockett's own words: "Great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems. And coaching is a different way. It's an alternative path that unlocks brilliance in your team." (Why coaching, not directing, builds both safety and capability.)