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

Lenny's Podcast: Product | Career | Growth

2025/11/23
Lenny's Podcast: Product | Career | Growth

Lenny's Podcast: Product | Career | Growth

2025/11/23
OverviewShownoteHighlightsTranscriptChaptersPins

Shownote

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 framewor...

Highlights

Leadership isn't about having all the answers—it's about asking the right questions. In this conversation, a seasoned executive coach unpacks how technical leaders can shift from being constant problem-solvers to empowering their teams through intentional coaching, emotional intelligence, and self-awareness.
14:24
Level Three listening uncovers emotional context and deepens connection instantly.
20:05
People often know the answer and need a nudge through curiosity and open-ended questions
25:29
Empowering teams through coaching freed up time for strategic work
39:23
Being coached leads to more commitment than being told what to do
42:03
People have more energy when working in their gifts and strengths.
53:42
Your gift isn't always what you're currently doing—recognize where you truly add value.
1:01:49
65% of startups fail due to co-founder conflict.
1:26:02
Fear can be a compass pointing to what you should do.
1:37:15
AI provides tactical advice between sessions based on client context and development plans

Chapters

Why leaders should stop giving answers and start coaching
00:00
When to guide versus when to decide: closing the leadership gap
17:13
How listening deeply unlocks team potential
25:29
From fixer to facilitator: creating space for empowered teams
36:44
Saying no as a strategy for energy and growth
42:03
Discovering your zone of genius to avoid burnout
53:42
Are you protecting your true strengths—or losing them to busyness?
1:01:49
Can your co-founder relationship survive without check-ins?
1:13:43
Using empathy, not blame, to transform difficult conversations
1:37:15

Transcript

Lenny Rachitsky: When clients come to you, what is the biggest gap they have that is keeping them from being successful as leaders? Rachel Lockett: Most leaders, especially technical leaders, assume they have to have all the answers. People have climbed t...