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

Lenny Rachitsky

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

Lenny Rachitsky•Nov 23, 2025

AI Summary

In this episode, executive coach Rachel Lockett shares practical frameworks for leadership, including when to coach versus direct, the GROW model for self‑solution, and strategies to make difficult conversations smoother. She discusses avoiding burnout by designing energizing careers, nurturing healthy co‑founder relationships, and aligning organizations with a one‑page plan, while also highlighting AI’s role in modern coaching. Lockett’s expertise, rooted in senior HR roles at Stripe and Pinterest, is demonstrated through a live coaching session, offering listeners actionable tools for building high‑trust teams and designing a life they love.

Why It Matters

These insights give CEOs and founders scalable methods to boost culture, productivity, and talent retention, directly impacting growth and resilience in tech‑driven organizations.

Episode Description

Executive Coach Rachel Lockett: When to coach vs. tell, preventing burnout, co-founder relationships, difficult conversations, and her one-page plan framework

Show Notes

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

Lenny Rachitsky – Nov 23, 2025

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 Lenny.

We discuss:

  1. When to coach and when to just tell people what to do – [09:00]

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

  3. Techniques for making difficult conversations less difficult – [01:20:28]

  4. Avoiding burnout and designing a more energizing career – [41:55]

  5. Building and sustaining a healthy co‑founder relationship – [01:06:50]

  6. Creating a one‑page plan that aligns your entire company – [01:31:47]

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

  8. Why you should ask, “Would I enthusiastically re‑hire this person?” to clarify talent decisions – [23:55]

Listen on YouTube →

Also available on Spotify and Apple Podcasts.

Where to find Rachel Lockett

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

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

Referenced resources

  • 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

  • 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

Recommended books

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

  • The 15 Commitments of Conscious Leadership – 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 collection – https://www.amazon.com/Roald-Dahl-Collection-Books-Box/dp/0241377293

My biggest takeaways from this conversation

(Content to be added by the reader.)

Comments

Want to join the conversation?

Loading comments...