A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
Timestamps are as accurate as they can be but may be slightly off. We encourage you to listen to the full context.
Podcast Summary
Executive coach and former HR leader Rachel Lockett delivers powerful frameworks for transforming leadership through coaching, difficult conversations, and emotional intelligence. (09:00) She demonstrates that great leaders know when to coach versus when to tell people what to do, showing how this shift unlocks brilliance in teams while preventing leader burnout. (41:55)
- Core focus: Shifting from being the person with all the answers to empowering teams through coaching, managing interpersonal dynamics effectively, and designing careers around personal strengths to avoid burnout
Speakers
Rachel Lockett
Rachel Lockett is an executive coach and former HR leader at Stripe and Pinterest who now works with CEOs, founders, and tech leaders on emotional intelligence, resilience, and leadership skills. She created coaching programs for Stripe's top 50 executives and has developed frameworks for co-founder relationships, difficult conversations, and leadership development that have helped scale multiple billion-dollar companies.
Lenny Rachitsky
Lenny Rachitsky is the host of Lenny's Podcast and author of Lenny's Newsletter, one of the most popular product management and growth publications. He previously worked at Airbnb as a Senior Product Manager and helps professionals in tech advance their careers through actionable insights and frameworks.
Key Takeaways
Master the Art of Coaching vs. Telling
Most technical leaders assume they must have all the answers, but this creates dependency rather than capability. (09:00) Rachel explains that when you constantly advise, "you're training your team to come to you with all of the hard problems" rather than equipping them to solve challenges independently. The key is shifting into curiosity when someone brings you a problem and helping them discover their own solution through powerful questions. Great leaders coach when the person has the right context and skills, and only advise when there's urgency or the person lacks necessary capabilities. This approach unlocks brilliance in your team and creates more motivated, self-sufficient team members.
Use Active Listening and the GROW Framework
Effective coaching requires mastering two core skills: active listening and powerful questions. (13:45) Active listening has three levels - internal (focused on yourself), focused (hearing their words), and global (understanding emotions, body language, and context beneath the words). The GROW model provides a structure for powerful questions: Goals (what does success look like?), Reality (what's your current situation?), Options (what paths could you take?), and Way forward (what will you do next?). (18:37) These tools create space for people to think through problems while feeling truly heard and understood.
Design Your Career Around Your Natural Gifts
Burnout often stems from spending too much time outside your zone of genius rather than just working too hard. (41:55) Rachel recommends tracking for two weeks what gives you energy versus what depletes you each day. When people operate from their natural strengths 80% of the time, they have dramatically more energy and inspiration. This requires intentional career design - telling your manager about your gifts, hiring around your weaknesses if you're a leader, and sometimes taking lateral moves to get into your strengths. As Rachel learned when a colleague told her "you're a people person, not a product strategist," recognizing and leaning into your gifts leads to both better performance and more fulfillment.
Transform Difficult Conversations with Mutual Understanding
The biggest mistake in difficult conversations is trying to prove your point rather than creating mutual understanding. (01:20:28) Rachel introduces the Nonviolent Communication framework: share Observations (facts only), express Feelings (emotions without blame), state Needs (universal human needs), and make Requests (specific, doable asks). This approach keeps you "on your side of the net" without crossing into blame or assumptions that trigger defensiveness. The goal isn't to convince someone they're wrong, but to help them understand your experience so they can empathize and respond constructively.
Strengthen Co-founder Relationships Like a Marriage
Sixty-five percent of startups fail due to co-founder conflict, making this relationship as critical as any marriage. (01:06:50) Strong co-founder relationships require two elements: self-awareness about your individual strengths and dynamics (using tools like the Enneagram), and intentional relationship maintenance through regular check-ins away from daily business operations. Just like couples need date nights, co-founders need dedicated time to discuss how they're working together, what's frustrating them, and how to align on vision and strategy. This "balcony time" away from the "dance floor" of operations prevents small issues from becoming relationship-ending conflicts.
Statistics & Facts
- Sixty-five percent of startups fail because of co-founder conflict, making the co-founder relationship one of the most critical factors in startup success. (01:06:50)
- Stripe processed just over $1.4 trillion last year, which works out to approximately 1.3% of global GDP, demonstrating the scale at which successful companies operate.
- According to Alpine Investors' data, portfolio companies that implement the People First operating rhythm with their one-page plan approach achieve higher returns compared to those that don't use this structured approach. (01:31:47)
