A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett
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What is the biggest leadership gap that keeps clients from succeeding?
When clients come to you, what is the biggest gap they have that is keeping them from being successful as leaders?
Most leaders, especially technical leaders, assume they have to have all the answers. People have climbed the ladder because they've been dependable, reliable, the smartest person in the room. But great leaders know that when you try to advise and have the answer all the time, you're not actually equipping your team to go solve the hard problems. You're training your team to come to you with all of the hard problems.
Difficult conversations are difficult. How do we help people make them less difficult?
We operate in tech, like we're supposed to give all of ourselves, all of our time, all of our energy to this endeavor, and it's purely logical. That's not at all true. It's completely emotional. Professionals have feelings. People, when they want to have a conflict, they come in ready to prove their point. There's a misguided view that the goal is to convince the other person that what they're doing is wrong. Actually, the goal of any conflict is to create mutual understanding. Understanding.
Talk about what you've learned about helping leaders in tech avoid burnout.
When people are in their gifts and their strengths, they have more energy. We all have more energy when we're operating from the things we naturally are good at. It's no one else's job to help you live in your gifts. What I notice in big companies is people are often annoyed or frustrated with their management for not making their job more interesting. No, your manager's job is to help you perform in the job you were hired to do. It's your job to navigate your career.
The power of this is this makes your life so much better.
Honey, let's try it. So I want you to tell me a challenge, something that you're struggling with.
The main thing I struggle with these days is just Today, my guest is Rachel Lockett, an executive coach and former longtime HR leader at Pinterest and at Stripe. She works with CEOs and founders and leaders at tech companies on both ways that they are emotional and positive intelligence, resilience and courage, and what they do, setting vision and strategy, prioritizing, and building trusted and accountable teams. She's someone I've heard a lot about over the years from other podcast guests, and this conversation. Conversation is powerful. It's jam-packed with advice and tips and frameworks that'll make you a better leader and also a better person. We even do a couple live coaching sessions to demonstrate some of Rachel's approaches, and as you'll see, I had a number of epiphanies during this conversation.
If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. It helps tremendously. And if you become an annual subscriber of my Newsletter, you get a year free of a ton of incredible products, including Devin Lovable, Replit, Bolt, Init, and Linear Superhuman, Descript, Whisper Full, Gamma, Perplexity, Warp, Granola, Magic Patterns, Raycast, Chapier D Mobbed, and Striped Atlas. Head on over to Lenny's Newsletter.com and click Product Pass. With that, I bring you Rachel Lockett after a short word from our sponsors. 1.3%. It's a small number, but in the right context, it's a powerful one. Stripe processed just over $1.4 trillion last year. That figure works out to be about 1.3% of global GDP.
It's a lot, but it's also just 1.3%. Stripe handles the massive scale and complexity of many of the world's fastest growing enterprises, including 78%. Of the Forbes AI 50 and more than half of the Fortune 100. There's a reason I've had more leaders from Stripe on this podcast than any other company. They know how to build great products that scale and that people love. Stripe is also a lot more than just payments. They've also got a category-leading billing solution and a highly optimized checkout experience built specifically to increase your checkout conversion. Enterprises like Atlas. Figma and Urban. Use Stripe to create fully branded and customized checkout pages with access to more than 125 global payment methods.
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Chapters
6 chapters
1
What is the biggest leadership gap that keeps clients from succeeding?
0:00–49:50
2
How can leaders use active listening to make people feel truly heard?
49:50–52:10
3
How can you align your work with your natural gifts and stay energized?
52:10–1:05:41
4
What practices help co‑founders build strong, healthy relationships?
1:05:41–1:19:16
5
How does the Non‑Violent Communication (NVC) framework make difficult conversations easier?
1:19:16–1:32:00
6
How is AI being used to enhance coaching and support clients between sessions?
1:32:00–1:45:15
Speakers
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