LLenny's Podcast
← All episodes
Rachel Lockett23 November 2025

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

8Frameworks
13Insights

Frameworks in this episode

Leadership5 steps

Balcony Rhythm for Co-Founder Relationships

Build shared self-awareness, then protect the relationship with vows and a real check-in cadence

Read →
Leadership4 steps

Coach vs. Advise Decision

Stop training your team to bring you every problem by knowing when to coach instead of solve

Read →
Self-Mastery5 steps

Energy Audit for Your Zone of Genius

Track what energizes and depletes you for two weeks, then redesign your role toward 80% in your gifts

Read →
Leadership4 steps

GROW Model for Powerful Questions

Four question categories that let people solve their own problem and walk away with a concrete next step

Read →
Communication4 steps

Non-Violent Communication (OFNR) for Difficult Conversations

Observation, feeling, need, request — get mutual understanding instead of trying to win the argument

Read →
Strategy4 steps

One-Page Plan and Operating Rhythm

Put vision through quarterly goals on one page, then meet in a rhythm to reflect on it

Read →
Leadership3 steps

The Enthusiastic Rehire Test

One binary question that cuts through months of avoided talent decisions

Read →
Communication4 steps

Three Levels of Listening

Drop from your own inner monologue into hearing what people communicate beneath their words

Read →

Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Myth Buster· 1

Myth Buster1:13:00

The Goal of Conflict Isn't to Win, It's Mutual Understanding

Rachel corrects the common belief that a difficult conversation is about proving the other person wrong. People walk in armored, ready to prove their point, but the actual goal of any conflict is to create mutual understanding. When she confronts her husband about parenting, her aim is to help him understand what she's struggling with so he can empathize, not to prove how little he's doing.

  • People enter conflict armored and ready to prove their point
  • The misguided view is that the goal is to convince the other person they're wrong
  • The real goal of any conflict is to create mutual understanding
  • Aim to help the other person empathize and see your struggle, not to prove them wrong

“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…”

Rachel Lockett · 1:13:00
#conflict#communication#difficult-conversations

Hot Take· 2

Hot Take57:00

It's Not Your Manager's Job to Make Your Work Interesting

Rachel pushes back on the common frustration that management should make your job more interesting. Your manager's job is to help you perform in the role you were hired to do; navigating your career and matching your gifts to the world's needs is your own responsibility. If your world right now is your company, understand its needs well enough to apply your strengths to them.

  • It's no one else's job to help you live in your gifts
  • People wrongly get annoyed at management for not making their job more interesting
  • Your manager's job is to help you perform in the job you were hired to do
  • Navigating your career and matching your gifts to needs is your own job

“no one else's job to help you live in your gifts.”

Rachel Lockett · 57:00

“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.”

Rachel Lockett · 57:00
#career#ownership#management#strengths
Hot Take1:17:30

Tech Pretends Work Is Purely Logical. It's Completely Emotional.

Rachel challenges the tech culture assumption that work is purely logical and that you should give all of yourself, your time, and energy to the endeavor. She argues it's completely emotional, professionals have feelings, and if you ignore those feelings they bubble up and you end up unconsciously acting from them. Naming actual emotions, not disguised judgments, is the key to human connection.

  • Tech operates as if work is purely logical and demands all of your time and energy
  • That's not true; work is completely emotional and professionals have feelings
  • Ignored feelings bubble up and you act unconsciously from them
  • A real feeling is an emotion word, not 'I feel like you're being a jerk'

“It also acknowledges that professionals have feelings.”

Rachel Lockett · 1:17:30

“I think that we operate in tech like we're supposed to give all of ourselves, all of our time, all of our energy to this…”

Rachel Lockett · 1:17:30
#emotions#workplace-culture#communication#tech

Explainer· 4

Explainer09:00

Why Great Leaders Coach Instead of Having All the Answers

Rachel Lockett explains that technical leaders climb the ladder by being the smartest, most dependable person in the room, so they assume leadership means always having the answer. But at a scaling company you have less context than your team, and defaulting to advice trains people to bring every hard problem back to you. Coaching is a learnable alternative that unlocks the team's own problem-solving.

  • Most technical leaders assume they must have all the answers because that is how they got promoted
  • When you scale, you have less context than the people around you, so the old operating mode breaks
  • Always advising trains your team to bring you every hard problem instead of solving them
  • Coaching is a learnable skill that shifts your energy into curiosity when someone brings a problem

“Most leaders, especially technical leaders, assume they have to have all the answers.”

Rachel Lockett · 00:00

“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…”

Rachel Lockett · 00:00
#leadership#coaching#management#technical-leaders
Explainer14:30

The Three Levels of Listening, and Why Leaders Need Level Three

Rachel breaks listening into three levels: level one is internal, where you're distracted by your own inner dialogue; level two is focused, where you can repeat back the words; and level three is global listening, where you hear beneath the words to tone, body language, and context. Great leaders drop into level three when influencing, selling, pitching vision, and coaching. She demonstrates it live by reflecting back not just Lenny's words about fatherhood but the emotion underneath them.

  • Level one listening is internal, consumed by your own inner dialogue while someone talks
  • Level two is focused listening where you can repeat back the person's words
  • Level three is global listening, hearing tone, body language, and context beneath the words
  • Active listening takes under a minute and creates emotional connection and motivation

“Level three listening listening is global listening. So, that's when I'm hearing beneath the words. I'm hearing what you're communicating, not just what you're saying.”

Rachel Lockett · 14:30
#listening#communication#coaching#emotional-intelligence
Explainer43:30

Why Working in Your Gifts Is the Antidote to Burnout

Rachel argues that burnout in tech comes from spending too much time outside your natural strengths. Leaders who stay inspired for years seem to have a hidden battery, and she attributes it to spending most of their time in their gifts. Her aspirational target is 80 percent of your time spent on what you're naturally good at and love, accepting that 20 percent will always be logistics you don't enjoy.

  • People burn out after years of pushing, not because they lack talent but because they leak energy
  • We all have more energy operating from what we're naturally good at and innately love
  • Technical founders often end up doing a completely different job than the one that plays to their strengths
  • The aspiration is 80 percent of your time in your gifts, with 20 percent unavoidable logistics

“We all have more energy when we're operating from the things we naturally are good at and the things we innately love doing.”

Rachel Lockett · 44:00

“So, my fitness test is 80%. That's the goal. That's the aspiration. You're always going to have 20% of things you don't love doing.”

Rachel Lockett · 52:30
#burnout#strengths#energy#career-design
Explainer1:01:30

Why Co-Founder Relationships Need Date Nights and Vows

Rachel treats the co-founder relationship like a marriage, noting that 65 percent of startups fail because of co-founder conflict. It's a tender, private relationship people don't feel comfortable discussing with their board, and it lacks support. Just as married couples need date nights, co-founders need deliberate time and space to check in on their alignment, and she advocates co-founder vows, recommitments, and regular check-ins.

  • 65 percent of startups fail because of co-founder conflict
  • The relationship is private and tender, like a marriage, with too few supports
  • Just like couples need date nights, co-founders need time and space to reconnect
  • She recommends co-founder vows, quarterly in-person check-ins, and regular renewals

“65% of startups fail because of co-founder conflict.”

Rachel Lockett · 1:01:30

“just like couples need a date night co-founders need time and space to connect with each other”

Rachel Lockett · 1:03:30
#co-founders#relationships#startups#conflict

Story· 2

Story24:30

The AI Founder Who Was the Blocker on Every Decision

Rachel shares the story of a client she calls Jeff, who ran an AI company while also acting as head of product. As his team and customer base grew he became overwhelmed and realized he was the blocker on every product and business decision, resenting it even though he had trained the team to work that way. Through coaching he built squads with clear KPIs and shifted from deciding everything to coaching in check-ins, ending up more energized with time to plan and work in his strengths.

  • Jeff was the bottleneck on every business and product decision and resented it
  • He had trained his team to bring him everything because he had always operated that way
  • The fix was squads with co-designed KPIs and a product review every two weeks
  • He shifted from deciding to coaching and freed himself to work on product vision and strategy

“soon he realized that he was the blocker on every decision, every business decision, every product decision and he was resenting it.”

Rachel Lockett · 25:00

“But with some coaching, he realized he was training his team to come to him with every decision because he had always operated that way.”

Rachel Lockett · 25:30
#founders#delegation#coaching#scaling
Story53:00

The Walk That Turned Rachel From a PM Into a Coach

Ten years ago Rachel moved from running UX research to a product manager role at Remind, leading twelve skeptical senior engineers. She got the team motivated and connected but was up at night agonizing over design and data decisions. On a walk, her colleague Zach Abrams told her that her gift wasn't being a product strategist, it was people, that she had motivated the team more than he ever could. She was offended, then realized he was right, got trained as a coach, and found her natural gifts.

  • Rachel led twelve skeptical senior engineers by listening and learning what users and the team needed
  • She got the team collaborating well but was stressing at night over product decisions that weren't her strength
  • Colleague Zach Abrams told her her zone of genius was people, not product strategy
  • She was offended at first, then embraced it, trained as a coach, and calls herself a work therapist

“your zone of genius or your gift is not being a product strategist, but I've watched you over the last few months and you have…”

Rachel Lockett (recounting Zach Abrams) · 54:30

“I'm basically a work therapist.”

Rachel Lockett · 55:30
#career-change#strengths#coaching#self-awareness

Q&A· 1

Q&A1:38:30

How Rachel Uses AI in Coaching, and What It Can't Replace

Asked how AI has changed coaching, Rachel describes using Granola to take session notes so she can be fully present and spot patterns across a client's history, and ChatGPT to brainstorm retreat ideas once she has the objectives set. She's building an AI tool to support clients between sessions, loaded with their development plan, goals, her frameworks, and the Granola notes, for tactical support before a tough meeting. She believes personal coaching stays critical for vision and behavior change while AI helps on tactics in between.

  • She uses Granola to capture session notes and surface patterns across a client's history
  • She uses ChatGPT to generate creative retreat ideas after setting core objectives
  • She's building a between-sessions AI bot loaded with each client's context and her frameworks
  • Personal coaching stays critical for life vision and behavior change; AI helps on tactics

“I'm experimenting with AI in a in a way to support my clients between sessions.”

Rachel Lockett · 1:38:30

“I see personal coaching as still critical for what is your vision of your life? How do you want to shift your core behavior to…”

Rachel Lockett · 1:39:30
#ai#coaching#tools#productivity

Tool· 2

Tool45:00

The Two-Week Energy Audit to Find Your Gifts

Rachel recommends a concrete exercise: for two weeks, every night, write down the five things that gave you the most energy that day and the five that depleted you most, then look for patterns. It reveals which natural gifts you're living in versus which draining tasks are causing a slow leak in your energy. She also suggests emailing five to ten people who know you well to ask what your strengths are, and scanning your calendar for what you look forward to versus dread.

  • For two weeks, log the five most energizing and five most depleting things each night
  • Patterns reveal your natural gifts versus the tasks slowly draining your tank
  • Alternatively email 5-10 people asking what shows up when you walk in the room
  • Scan your calendar for recurring themes of what you're excited to do versus what you dread

“it's like a slow leak in your gas tank that over time shows up in your daily amount of energy.”

Rachel Lockett · 45:30
#burnout#strengths#self-awareness#productivity
Tool1:27:30

The Stripe Question: Would You Enthusiastically Rehire Them?

When leaders avoid a talent conversation because they keep getting let down, Rachel asks a binary question they used at Stripe: would you enthusiastically rehire this person for the same role? People have an immediate physical, honest reaction, and if the answer is no, no amount of difficult conversations will fix it. A no doesn't mean fire them immediately; it means you need to do something, whether a performance plan, a role change, or a search.

  • The clarifying question is whether you'd enthusiastically rehire this person for the same role
  • It's binary and prompts an immediate, honest, full-body reaction
  • If the answer is no, more difficult conversations alone won't make it work
  • A no means take action, not necessarily an immediate firing

“would you enthusiastically rehire this person for the same role? Which is the question we always asked at Stripe?”

Rachel Lockett · 1:27:30
#hiring#talent#performance-management#leadership

Takeaway· 1

Takeaway12:30

When You Should Just Tell People What to Do

Coaching is not always the right move. Rachel gives clear heuristics for when to advise instead: when the issue is urgent, when the person genuinely lacks the skill, and when you already know the answer you want driven. Turning a moment like that into a guessing game where the report has to read your mind is a bad use of coaching.

  • Advise when the issue is urgent and you have a specific answer you want driven
  • Advise when the person coming to you lacks the skill they need
  • Don't turn coaching into a game where the person has to guess what's in your mind
  • Leaders over-index on advising even when their hired experts could solve it themselves

“It's an urgent issue and you actually have an answer that you want to drive.”

Rachel Lockett · 12:30
#coaching#management#decision-making