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

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