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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:* 1. When to coach and when to just tell people what to do 2. The GROW technique for helping people figure out a solution for themselves 3. Techniques for making difficult conversations less difficult 4. Avoiding burnout and designing a more energizing career 5. Building and sustaining a healthy co-founder relationship 6. Creating a one-page plan that aligns your entire company 7. Practical ways AI is transforming executive coaching and leadership development 8. Why you should ask, “Would I enthusiastically rehire this person?” to clarify talent decisions *Brought to you by:* Stripe—Helping companies of all sizes grow revenue: https://stripe.com/ Vanta—Automate compliance. Simplify security: https://vanta.com/lenny Persona—A global leader in digital identity verification: https://withpersona.com/lenny *Transcript:* https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations *My biggest takeaways (for paid newsletter subscribers):* https://www.lennysnewsletter.com/i/178940830/my-biggest-takeaways-from-this-conversation *Where to find Rachel Lockett:* • LinkedIn: https://www.linkedin.com/in/rhlockett/ • Website: https://www.lockettcoaching.com *Where to find Lenny:* • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ *In this episode, we cover:* (00:00) Introduction to Rachel Lockett (04:58) The human side of business building (09:00) Coaching vs. advising (13:09) Skill 1: Active listening (18:37) Skill 2: Powerful questions (24:49) Real-life coaching example (27:36) Live coaching example with Lenny (41:55) Addressing burnout in tech (51:03) Spending more time working toward your goals (53:09) Discovering her passion for executive coaching (57:36) It's your job to navigate your career (58:44) Why Rachel says to start small (01:00:49) Building strong co-founder relationships (01:06:50) Handling co-founder conflicts (01:12:35) Improving interpersonal skills with team members (01:20:28) Reframing difficult conversations as growth opportunities (01:31:47) The one-page plan for company alignment (01:36:50) Leveraging AI in coaching and personal development (01:42:04) Lightning round and final thoughts *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 ...References continued at: https://www.lennysnewsletter.com/p/a-guide-to-difficult-conversations _Production and marketing by https://penname.co/._ _For inquiries about sponsoring the podcast, email [email protected]._ Lenny may be an investor in the companies discussed.

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