Lenny’s Podcast: Product | Career | Growth

A Guide to Difficult Conversations, Building High-Trust Teams, and Designing a Life You Love

Guest: Rachel Lockett (Executive Coach, former HR leader at Pinterest & Stripe)
Host: Lenny Rachitsky
Air Date: November 23, 2025

Overview

In this episode, executive coach Rachel Lockett shares actionable frameworks and insightful stories about leadership, handling difficult conversations, building high-trust teams, and intentionally designing a fulfilling work and life experience. Rachel draws on her experience coaching CEOs, founders, and leaders at high-growth tech companies, emphasizing the power of self-awareness, coaching over telling, and living in your strengths. Lenny participates in a live coaching session, demonstrating Rachel’s tools in real time.

Key Discussion Points & Insights

1. The Human Side of Leadership

• Rachel’s hope for listeners: “I hope that your listeners take away that the human side of business building is incredibly fun and impactful and that it’s easy to do. They can do it with simple tools.”
  (05:22, Rachel)

• The challenge for leaders is often not knowledge, but vulnerability and willingness to seek help. Leaders thrive when they invest in understanding the talents and needs of their teams.

• Lenny: “If you really understand the talent around you and you create an environment where they can be successful, your business will thrive.”
  (05:55, Rachel summarizes the core idea)

2. Coaching vs. Telling: Developing High-Trust, Accountable Teams

Coaching Is a Learnable Skill

• Many technical leaders assume they must have all the answers, but this leads teams to depend on their leader for every decision—slowing growth and sapping motivation.
• Rachel advocates for shifting from “solving” to “coaching,” which unlocks brilliance in others.

“Great leaders know that when you try to advise and have the answer all the time, you’re not actually equipping your team… you’re training your team to come to you with all of the hard problems.”
(09:24, Rachel)

When to Advise vs. Coach

• Advise: If it’s urgent, or the person lacks necessary skills.
• Coach: When the person has the context and capability to figure it out.

“Coaching is an alternative path that unlocks brilliance in your team and is way more motivating for the people around you.”
(09:58, Rachel)

Basic Coaching Tools for Leaders

• Active Listening:
  • Level 1: Internal (self-focused)
  • Level 2: Focused (repeat back words)
  • Level 3: Global (read between lines, observe emotions, tone, body language)
• Powerful Questions:
  • Use the GROW model
    • Goals: What does success look like?
    • Reality: What’s happening now?
    • Options: What could you do?
    • Way Forward: What will you do next?

“Dropping into level three listening is what great leaders do when they’re influencing, when they’re selling, when they’re pitching a vision, and definitely when they’re coaching.”
(15:11, Rachel)

3. Live Coaching Demonstration [27:37–40:30]

Rachel coaches Lenny on managing “endless work” and the “Indiana Jones boulder” effect of constant demands. She uses GROW to help Lenny:

• Articulate his goal (more free time, higher creativity)
• Identify obstacles (habit of saying yes, filling spare time with more tasks)
• Brainstorm options (skip newsletters, enforce boundaries, delegate more)
• Outline next steps (skip a newsletter week, revisit criteria for accepting new commitments)

“Every time you say yes to something, think about the trade-off, because you’re saying no to something else that you actually want.”
(38:58, Rachel)

4. Avoiding Burnout and Finding Your Zone of Genius [42:46–57:18]

Diagnose Burnout

• Burnout is common among high-performing leaders; renewal and preventing burnout means operating in your strengths (“gifts”) as much as possible (~80% is the goal).
• Rachel recommends a 2-week self-inventory:
  • Each night, write 5 activities that energized you and 5 that depleted you.
  • Spot patterns and openly communicate strengths/interests to peers and managers.

“When people are in their gifts and their strengths firmly, most of the time, they have more energy… You can design your life so you’re spending 80% of your time in your gifts.”
(44:34, Rachel)

Taking Action to Rebalance

• Share your goals and development areas proactively with managers.
• It’s your responsibility to navigate your career into a role matching your strengths—don’t expect your manager to do this for you.

“It’s no one else’s job to help you live in your gifts.”
(57:18, Rachel)

5. Building High-Trust Co-Founder and Team Relationships [60:39–76:50]

Co-Founder Relationships

• Self-awareness is foundational: know your own and your partner’s strengths and values.
• Use explicit “co-founder vows”: concrete commitments to each other, regularly reviewed.
• Make space for the relationship—regular check-ins, open dialogue, and physical (or virtual) time together.

“Just like couples need a date night, co-founders need time and space to connect with each other, to come together and say, ‘how’s this working for you?’”
(62:32, Rachel)

Conflict and Difficult Conversations

• The goal in conflict is not to “win” or convince, but to create mutual understanding.
• Everyone has a role in contributing to a conflict—look for your responsibility.
• Use Nonviolent Communication (NVC) (Marshall Rosenberg):
  1. Observation: Just the facts—what happened.
  2. Feelings: Express your emotion (not blaming).
  3. Needs: Identify your underlying human needs.
  4. Request: A concrete, do-able ask.

“The goal of any conflict is to create mutual understanding.”
(27:27 & 72:50, Rachel)
“Genuinely, professionals have feelings… If we ignore our feelings, they will bubble up and we will be unconsciously acting from them.”
(77:36, Rachel)

Reframing “Difficult Conversations”

• Treat points of fear/discomfort as compasses for personal growth.
• “If there’s something you’re afraid of, that is a sign you should do that. The cave you fear contains the treasure you seek.”
  (86:39, Lenny paraphrasing guiding wisdom)

6. Creating Effective Team Operating Rhythms [91:48–96:44]

• Rachel recommends a simplified One-Page Plan approach:

  • Clearly state your Vision and Values
  • Strategic intent and KPIs
  • Annual and then Quarterly goals
  • Make everything visible and transparent, so anyone can see how their work connects to the big picture

• The rhythm of reflection and alignment is as important as the plan: regular offsites, team reflections, and honest retrospectives.

“It’s not just about having a plan, it’s about how you create it, how you reflect on it, and how you come together around it.”
(94:41, Rachel)

7. The Future of Coaching and AI [97:13–100:47]

• Rachel uses AI tools (like Granola and ChatGPT) to manage coaching notes, plan retreats, and is experimenting with ways to offer clients AI-powered support between sessions.
• She sees AI augmenting (but not replacing) human connection and personal coaching.

Notable Quotes & Memorable Moments

• On active listening:
  “Most people aren’t listening, they’re just waiting for their turn to talk. This is rampant in tech, and great leaders flip that script and tune in.” (13:31, Rachel)

• On setting boundaries and taking back time:
  “Be careful working for yourself if your boss is a workaholic.” (27:51, Lenny, self-reflection)

• On mutual understanding in conflict:
  “Actually, the goal of any conflict is to create mutual understanding.” (27:27 & 72:50, Rachel)

• On moving toward your gifts:
  “If you can see your path laid out in front of you, step by step, it’s not your path. Your own path you make with every step you take. That’s why it’s your path.” (103:06, Joseph Campbell quote via Rachel)

• On co-founder alignment:
  “There should be some element of love for your co-founder. In fact, I think when you work closely with colleagues and you really are able to see their gifts and enable them, you can’t help but love them.” (71:21, Rachel)

Timestamps for Key Segments

• The Human Side of Leadership: 05:03–06:22
• Coaching vs. Telling – Live example: 09:24–27:37
• Live Coaching with Lenny: 27:37–40:30
• Avoiding Burnout & Zone of Genius: 42:46–57:18
• Co-Founder/Team Relationship Tips: 60:39–66:50
• NVC & Difficult Conversations: 72:50–80:29
• Designing Team Operating Rhythms: 91:48–96:44
• AI & Future of Coaching: 97:13–100:47
• Lightning Round/Favorite Resources: 102:11–104:28

Further Resources/References

• 15 Commitments of Conscious Leadership (Recommended Book)
• Designing Your Life by Bill Burnett (Recommended Book)
• Nonviolent Communication by Marshall Rosenberg (Framework and Book)
• One-Page Plan/People First Operating Rhythm (Alpine Investors)
• GROW Coaching Model (Widely used coaching tool)

Closing Thoughts

Rachel’s frameworks and lived examples offer clear, actionable steps for leaders at any level to build high-trust cultures, navigate tough situations, and design careers that energize. If you’re committed to growth—as a product builder or people leader—her guidance and tools are both inspirational and practical.

Learn more or contact Rachel at: [lockettcoaching.com]

“Building businesses is an inherently human endeavor… I want to encourage listeners to connect with the people around them, lead healthier teams, create environments where connection is inevitable, and they will have more fun and build better businesses because of that.”
– Rachel Lockett (101:07)