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A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett

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Nov 23, 2025

Guest

Rachel Lockett

Rachel Lockett, an executive coach and former HR leader at Stripe and Pinterest, shares insights on emotional intelligence and leadership. She discusses when to coach versus give advice, introducing the GROW technique to empower others. Rachel emphasizes avoiding burnout by aligning roles with strengths and suggests practical energy tracking methods. She also explores the dynamics of co-founder relationships, advocating for regular check-ins and effective communication strategies to transform conflicts into growth opportunities.

01:45:19

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Episode notes

00:00 / 00:00

Use The GROW Coaching Model

Apply the GROW model: Goal, Reality, Options, Way forward to coach decisions.
Ask open questions in those four areas to surface answers the person already knows.

00:00 / 00:00

Founder Shifted From Solver To Coach

Jeff shifted from deciding everything to coaching squads with KPIs and product reviews.
The squads moved faster and he regained time for vision and strategy work.

00:00 / 00:00

Measure What Energizes You

Track five energizers and five drains each day for two weeks to spot patterns.
Use results to redesign your role so you spend ~80% of time in your strengths.

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Human side of building teams

02:44 • 2min

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Coaching shifts leaders' energy

05:06 • 8min

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Active listening levels

13:31 • 5min

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Powerful questions and the GROW model

18:38 • 9min

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Live coaching: reducing endless work

27:37 • 12min

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When to give advice vs coach

Avoiding burnout by living your gifts

42:47 • 5min

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Practical ways to find your strengths

Strengths-aligned careers and role swaps

01:00:13 • 43sec

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Co-founder dynamics and self-awareness

01:00:56 • 3min

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Co-founder rituals and vows

01:03:34 • 4min

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Repairing tense co-founder relationships

01:07:27 • 5min

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Nonviolent Communication for hard talks

01:12:50 • 8min

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Reframing conflict as growth

01:21:12 • 5min

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Talent clarity: would you rehire them?

01:25:47 • 7min

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One-page plan and operating rhythm

01:32:18 • 5min

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AI's role in coaching and tools

01:36:52 • 4min

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Loneliness, connection, and leadership

01:40:56 • 1min

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Lightning round and recommendations

• Mentioned in 73 episodes

Nonviolent Communication

A Language of Life

Marshall B. Rosenberg

Nonviolent Communication (NVC) is a framework created by Marshall Rosenberg that aims to enhance communication by promoting compassion and empathy. The book outlines a four-step process for effective communication: observing what is happening without judgment, identifying and expressing feelings, recognizing and articulating needs, and making clear requests. Rosenberg emphasizes the importance of separating observations from evaluations to avoid defensiveness and promote genuine human connections. The book includes practical exercises, role-plays, and real-life examples to illustrate how NVC can be applied in various relationships and situations, including personal, professional, and conflict resolution contexts. It also discusses how NVC can help in developing self-compassion and resolving conflicts by focusing on the underlying needs rather than the actions that trigger emotions.

#759

• Mentioned in 43 episodes

The 15 Commitments of Conscious Leadership

A New Paradigm for Sustainable Success

Diana Chapman

Kaley Warner Klemp

Jim Dethmer

This book distinguishes between unconscious and conscious leadership, offering a roadmap to help leaders transition from fear-based to trust-based leadership. The 15 commitments outlined in the book aim to enhance self-awareness, accountability, and collaborative relationships. By practicing these commitments, leaders can achieve more energy, clarity, focus, and healthier relationships, both personally and within their teams. The commitments include ending blame and criticism, speaking candidly, finding unique genius, and creating win-for-all solutions, among others. The authors provide practical exercises and resources to help leaders implement these commitments effectively.

#412

• Mentioned in 67 episodes

Designing your life

How to Build a Well-Lived, Joyful Life

Dave Evans

Bill Burnett

Bill Burnett and Dave Evans

In this book, Bill Burnett and Dave Evans apply the principles of design thinking to help readers design and build a life that is both meaningful and fulfilling. The authors, who are also educators at Stanford University, emphasize the importance of prototyping, experimentation, and iteration in life design. They provide practical exercises and tools to help readers navigate life's challenges and create a future that aligns with their values and aspirations. The book is based on their highly successful course at Stanford and has been widely praised for its empowering and practical approach to life design.

Rachel Lockett is a sought-after 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. In this episode, Rachel shares powerful frameworks for coaching reports, having difficult conversations, avoiding burnout, and strengthening co-founder relationships. She also demonstrates these techniques through a live coaching session with me.

We discuss:

* When to coach and when to just tell people what to do [09:00]

* The GROW technique for helping people figure out a solution for themselves [18:37]

* Techniques for making difficult conversations less difficult [01:20:28]

* Avoiding burnout and designing a more energizing career [41:55]

* Building and sustaining a healthy co-founder relationship [01:06:50]

* Creating a one-page plan that aligns your entire company [01:31:47]

* Practical ways AI is transforming executive coaching and leadership development [01:36:50]

* Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions [23:55]

Also on Spotify and Apple Podcasts

Brought to you by:

Stripe—Helping companies of all sizes grow revenue

Vanta—Automate compliance. Simplify security.

Persona—A global leader in digital identity verification

Where to find Rachel Lockett:

• LinkedIn: https://www.linkedin.com/in/rhlockett/

• Website: https://www.lockettcoaching.com

Referenced:

• One-page plan template: https://www.lockettcoaching.com/#resources

• Lockett Coaching Leadership Toolkit: https://www.dropbox.com/scl/fi/s74a9cn1ka1ebz6pglypf/Leadership-Toolkit_-Coaching-Rachel-Lockett.pdf?rlkey=yg2m9df2ziwy0fa6p0dt4gcfu&st=dgzvnf76&dl=0

• Renew Your Co-Founder Vows—and Other Tactics for Strengthening the Most Important Relationship in Your Startup: https://review.firstround.com/five-practices-to-strengthen-your-co-founder-relationship/

• First Round Guide to Co-Founder Check-Ins: https://docs.google.com/document/d/1yUosmfMuE-8-sAwPrEPDcGqkJLVLWg5dC2_8lcXm7U4/edit?tab=t.0

• Coinbase: https://www.coinbase.com

• Management Time: Who’s Got the Monkey?: https://hbr.org/1999/11/management-time-whos-got-the-monkey

• Chuck Palahniuk’s quote from Fight Club: https://www.goodreads.com/quotes/1338270-people-don-t-listen-they-just-wait-for-their-turn-to

• Patrick Collison on X: https://x.com/patrickc

• Stripe: https://stripe.com

• Remind: https://www.remind.com

• Zach Abrams on LinkedIn: https://www.linkedin.com/in/zacharyabrams

• Brex: https://www.brex.com

• Bridge: https://www.bridge.xyz

• Superhuman’s secret to success: Ignoring most customer feedback, manually onboarding every new user, obsessing over every detail, and positioning around a single attribute: speed | Rahul Vohra (CEO): https://www.lennysnewsletter.com/p/superhumans-secret-to-success-rahul-vohra

• Zigging vs. zagging: How HubSpot built a $30B company | Dharmesh Shah (co-founder/CTO): https://www.lennysnewsletter.com/p/lessons-from-30-years-of-building

• The Enneagram Institute: https://www.enneagraminstitute.com

• How to build deeper, more robust relationships | Carole Robin (Stanford GSB professor, “Touchy Feely”): https://www.lennysnewsletter.com/p/build-robust-relationships-carole-robin

• How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC): https://www.lennysnewsletter.com/p/jerry-colonna

• How Netflix builds a culture of excellence | Elizabeth Stone (CTO): https://www.lennysnewsletter.com/p/how-netflix-builds-a-culture-of-excellence

• What Is PeopleFirst?: https://alpineinvestors.com/story/what-is-peoplefirst

• How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors): https://www.lennysnewsletter.com/p/how-to-break-out-of-autopilot-graham-weaver

• Granola: https://www.granola.ai

• KPop Demon Hunters on Netflix: https://www.netflix.com/title/81498621

• Loom: https://www.loom.com

• Joseph Campbell’s quote: https://www.goodreads.com/quotes/21396-if-you-can-see-your-path-laid-out-in-front

• Wes Anderson’s short films (Roald Dahl) on Netflix: https://www.netflix.com/tudum/articles/wes-anderson-netflix-short-films

Recommended books:

• Nonviolent Communication: A Language of Life: Life-Changing Tools for Healthy Relationships: https://www.amazon.com/Nonviolent-Communication-Language-Life-Changing-Relationships/dp/189200528X

• The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success: https://www.amazon.com/15-Commitments-Conscious-Leadership-Sustainable/dp/0990976904

• Designing Your Life: How to Build a Well-Lived, Joyful Life: https://www.amazon.com/Designing-Your-Life-Well-Lived-Joyful/dp/1101875321

• Roald Dahl books: https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.

My biggest takeaways from this conversation:

To hear more, visit www.lennysnewsletter.com

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