Many leaders avoid difficult conversations until it's too late - and that avoidance destroys trust, creates resentment, and turns manageable issues into existential crises. Rachel Lockett, executive coach and former HR leader at Stripe and Pinterest, reveals practical frameworks for productive conflict, building high-trust teams, and creating sustainable success without burning out.

Rachel has spent over a decade coaching CEOs, founders, and senior leaders at tech companies from early-stage startups to scale-ups. In this pod conversation with Lenny, she shares concrete tools for difficult conversations and the "one-page plan" operating rhythm that keeps teams aligned without bureaucracy - and demonstrates exactly how these frameworks work through live coaching sessions.

Most technical leaders climb the ladder by being the smartest person in the room - reliable, dependable, always having the answer. This strength becomes their Achilles' heel in leadership.

"Most leaders, especially technical leaders, assume they have to have all the answers," Rachel explains. "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 solve hard problems. You're training them to come to you with every problem."

This creates a vicious cycle: leaders become bottlenecks, teams become dependent, leaders burn out. The shift is profound - from having all the answers to asking the right questions, from solving problems to building problem-solvers.

The antidote is "level three" listening - not just hearing words, but understanding emotions, body language, context, and unstated needs. At this level, leaders reflect back insights the speaker isn't fully aware of themselves.

Key Takeaways:

When people approach conflict, they enter ready to prove their point and convince the other person they're wrong. This adversarial approach guarantees defensiveness. Rachel introduces a powerful alternative: the NBC framework for non-violent communication.

Observation - Share objective facts without interpretation or judgement. "I noticed you didn't close the fridge fully" rather than "You always leave the fridge open."

Feelings - Express genuine emotion. This must be an actual emotion (frustrated, anxious, disappointed) not disguised judgement ("I feel like you're being a jerk" isn't a feeling). Professionals have feelings, and ignoring them doesn't make them disappear.

Needs - Identify the core human need that wasn't met: autonomy, consideration, respect, safety, or connection. This moves conversation from blame to understanding what truly matters.

Request - Make a specific, actionable ask that addresses the need. Not a demand, but a clear request the other person can honour or discuss.

"The goal of any conflict is to create mutual understanding," Rachel emphasises. "It's not to convince the other person that what they're doing is wrong." This transforms conflicts from battles into opportunities for connection.

The framework works because it keeps you on "your side of the net" - sharing your experience rather than making assumptions about intentions. When you lead with vulnerability, others naturally reciprocate.

Key Takeaways:

There's a dangerous myth in ‘tech’ that work should be purely logical, unemotional, and demand "all of ourselves, all of our time, all of our energy." This fiction ignores a fundamental truth: professionals have feelings.

"We operate in tech like it's purely logical," Rachel observes. "That's not at all true. It's completely emotional. If we ignore our feelings, they bubble up and we unconsciously act from them."

When organisations pretend emotions don't exist, people don't stop having feelings - they stop talking about them. Emotions go underground, manifesting as passive-aggressive behaviour, unexplained resistance, team dysfunction, and attrition. Avoiding emotional topics creates more drama, not less.

Acknowledging emotions makes teams more effective. When people name feelings and needs explicitly, issues get resolved faster with less collateral damage. The alternative - letting resentment build until someone explodes or quits - is far more disruptive.

Remote work amplifies this challenge. Without casual face-to-face interactions, emotional cues are harder to read. Leaders must actively create space for genuine connection, not just task-focused Zoom calls.

Key Takeaways:

Most people operate at "level one" listening - distracted by their own inner dialogue whilst someone else speaks. This is the default state, especially when rushed or stressed.

"Level one listening is internal," Rachel explains. "I'm thinking about the implications of that problem on me. I'm completely distracted with my own inner dialogue. Most people go through their world rushed and in level one."

Level two is focused - actively paying attention to words, able to repeat them back. This happens in good one-on-ones when problem-solving together. Functional but limited.

Level three is where transformation happens. This is global listening - hearing beneath the words, noticing body language, tone, what's being communicated beyond what's said. At this level, you understand full context and reflect back insights the speaker isn't fully aware of themselves.

Rachel demonstrates this in a live coaching segment. When Lenny describes being a father, she notes: "Initially, I saw you squirm in your chair. You looked up and down and avoided my eye contact at first because my sense is you love being a dad. And it's so challenging. It's so tiring. I'm hearing both of that in your answer."

This attentiveness creates psychological safety. People feel truly seen, making them more open to challenge and change. Leaders who master level three listening become people others actively seek out for difficult conversations.

Key Takeaways:

A common struggle for leaders is saying no without guilt or damaging relationships. The default is either saying yes to everything (burnout) or saying no in ways that create resentment.

Even successful leaders struggle. During a coaching segment, Lenny admits filling his calendar the moment he feels free, committing to more than sustainable.

The solution isn't willpower - it's understanding what saying yes costs. Rachel asks: "How is that commitment to saying yes serving you?" When Lenny admits "Not great," she explores what benefits he gets from this pattern.

Through questioning, it becomes clear saying yes serves needs like staying relevant, maintaining opportunities, and feeling productive. But the cost is enormous - less time for creative exploration (his actual fuel), less time with family, and constant overwhelm.

The key insight: current ways of operating aren't random - they serve some need, even unconsciously. Understanding what you're getting from the pattern lets you find healthier ways to meet those needs. Then saying no becomes easier because you see clearly what you're saying yes to instead.

Rachel suggests reframing from "How do I say no?" to "What am I saying yes to by saying no?" If declining a speaking engagement means saying yes to creative exploration time (which fuels better work long-term), the choice becomes clearer.

Key Takeaways:

As companies scale, they swing between chaotic lack of structure or suffocating bureaucracy with endless OKRs and planning documents. Rachel introduces an elegant alternative: the one-page plan.

The concept is deceptively simple - every team or project has a single page (literally one page, not 47 slides) capturing: goal, key metrics, success definition, owners, and needed support. That's it. [NB I am a HUGE fan of this; can’t recommend it enough!]

"At Stripe, teams would create this one-page plan," Rachel explains. "It had the goal, the metrics, the definition of success, the owners, and what they needed from other teams. Everyone could see everyone else's one-page plan. It created alignment without bureaucracy."

The power comes from constraints. When you can only use one page, you're forced to clarify what actually matters. No room for fluff, CYA statements, or vague aspirations. Just essential information.

Critically, one-page plans were visible across teams. This transparency created natural coordination - teams could see dependencies, identify conflicts early, and offer help without a centralised programme management office. The system was self-organising.

The one-page plan serves as a living document, updated regularly as reality unfolds. Unlike annual planning exercises that become instantly obsolete, this approach acknowledges plans change and makes updating frictionless. If you can't fit your update on one page, you're probably not clear enough about what changed.

This works best for companies between 50 and 500 people - large enough to need coordination, small enough to maintain transparency. Below 50, informal communication often suffices. Above 500, you may need more structure, but the principle of radical simplicity still applies.

Key Takeaways:

Rachel shares a pivotal moment that shaped her entire approach to coaching. Working as a product manager at Remind, she was asked to lead product management for the core product.

Initially, she was excited - a promotion, a chance to be "where strategy happens." Within a month, she had a sceptical team of 12 senior engineers working effectively, disagreeing productively, and feeling more connected to users.

"But what I was also doing is I was at home stressing in the middle of the night about the new user experience," Rachel recalls. "I couldn't decide which designs to go with. I was always overleveraging our data scientists and swirling on decisions that didn't need so much stress."

Then colleague Zach Abrams pulled her aside during a walk: "Rachel, your zone of genius is not being a product strategist. I've watched you over the last few months and you've gotten the team more motivated than I ever could and you've influenced the entire executive team behind your ideas. You're a people person."

At first, Rachel felt offended. But sitting with the feedback, she realised he was right. Both her parents were therapists (she'd actively avoided that path), yet here she was, essentially being a work therapist. She loved entrepreneurial energy and big vision, but her gift was developing people and building high-trust teams.

This led her to train as a coach and eventually move into HR leadership at Pinterest and Stripe before founding her coaching practice. Meanwhile, Zach led product at Coinbase, Brex, and most recently Bridge (acquired by Stripe). Both honoured their respective zones of genius.

Rachel's "80/20 rule" is aspirational: spend 80% of time in your natural gifts, 20% on logistics and necessary tasks that don't energise you. When you're in your gifts, you have dramatically more energy. The inverse - spending most time in activities that drain you - is the express path to burnout.

The practical implication: regularly audit where your energy comes from. What activities leave you energised versus depleted? What feels like "work" versus "play"? Then actively reshape your role towards your gifts, even if that means delegating or eliminating responsibilities that look impressive on paper but drain your spirit.

Key Takeaways:

Building high-trust teams isn't about trust falls - it's about creating psychological safety through consistent, small actions over time. Trust is earned through vulnerability, reliability, and willingness to have difficult conversations early.

One surprising insight: co-founders often create the least trusting relationships because they never establish fundamental structures other team members have. Unlike manager-report relationships with regular one-on-ones and clear feedback mechanisms, co-founders often just "wing it," assuming their shared mission is enough.

"Co-founders sometimes create the most damage in an organisation because they're not aligned," Rachel notes. "They're avoiding feedback with each other because 'we're in this together.' But that avoidance creates confusion for everyone else."

The solution is counterintuitive: co-founders need MORE structure, not less. Regular check-ins (weekly or bi-weekly) to explicitly discuss working relationship issues, not just business strategy. Clear agreements about decision-making authority in different domains. Permission to give each other direct feedback without threatening the partnership.

High-trust teams have what Rachel calls "permission to be human" - acknowledging that people have emotions, personal lives, and variable capacity. When a team member is going through a difficult time, high-trust teams don't pretend nothing is happening. They name it, adjust expectations temporarily, and offer support.

Crucially, high trust doesn't mean everyone likes each other or never disagrees. High-trust teams have MORE conflict, not less - but it's productive conflict where people challenge ideas without attacking each other personally. Trust provides safety to disagree vehemently whilst assuming positive intent.

Creating this environment requires leaders to model vulnerability first. Share when you don't have the answer. Admit mistakes publicly. Ask for help when you need it. This gives permission for everyone else to do the same, creating a culture where people show up as whole humans rather than curated professional personas.

Key Takeaways:

Rachel is building an AI coaching assistant that sits between regular sessions with clients. It won't replace human coaching (deep strategic and behavioural change still requires human connection), but it can provide tactical support in the moment.

The system would have access to the client's coaching session notes, development plan, Rachel's core frameworks, and training background. When a client faces a specific challenge - "I'm anxious about this team meeting, how should I approach it?" - they get personalised guidance based on everything they've worked on together.

"I see personal coaching as still critical for what is your vision of your life? How do you want to shift your core behaviour?" Rachel explains. "But AI can play a helpful role in between on the tactics."

This acknowledges a reality: clients often want more support between sessions but are reluctant to "bother" their coach. An AI assistant with full context removes that friction whilst preserving the human relationship for deeper transformational work.

Rachel sees her role as helping leaders "bring humans together to self-actualise" - fighting against the default state of blind grind and isolation. The AI tool enhances human connection, not replaces it, by handling routine tactical questions so human coaching time focuses on what truly requires a human.

This fits a broader pattern in how AI should augment professional work - not replacing human expertise but handling repetitive, pattern-matching work so humans focus on creativity, empathy, strategy, and relationship-building. The future isn't human OR AI, it's thoughtfully designed human AND AI collaboration.

Key Takeaways:

The frameworks Rachel shares are immediately applicable to challenges you're facing now. Whether it's a difficult conversation you've been avoiding, a co-founder relationship that needs attention, or your own path towards burnout, you can start making changes today.

For difficult conversations: Use the NBC framework next time you need to address an issue. Write out your Observation (facts only), Feelings (actual emotions), Needs (core human need), and Request (specific ask) before the conversation. This preparation alone often shifts your mindset from adversarial to collaborative.

For team dynamics: Implement one-page plans for your current projects. The constraint of one page forces clarity and eliminates vague language. Make them visible across teams to enable self-organising coordination.

For burnout prevention: Audit where you're spending time against where you feel energised versus drained. Look for opportunities to delegate, eliminate, or redesign responsibilities outside your zone of genius. No one else will do this work for you.

For building trust: Model vulnerability as a leader. Share when you don't have the answer. Admit mistakes publicly. Ask for help openly. This gives permission for your team to do the same, creating the psychological safety high-trust teams require.

For co-founder relationships: If you're in a co-founder dynamic, establish regular working relationship check-ins separate from business strategy discussions. Create explicit agreements about decision-making authority in different domains. Give each other permission to share direct feedback.

The common thread through Rachel's frameworks is that connection and clarity aren't opposed to high performance - they're essential enablers of it. Teams that have difficult conversations productively move faster, not slower. Leaders who operate from their zone of genius have more impact, not less. Companies that acknowledge the human side of work build better products and attract better talent.

As Rachel powerfully concludes: "I want to encourage listeners to think of themselves as leaders who bring humans together to self-actualise and that they have to actively overcome the default state which is blind grind and loneliness. They will have more fun and build better businesses because of that."

Key Takeaways:

About Rachel Lockett: Executive coach working with CEOs, founders, and leaders at tech companies. Former HR leader at Stripe and Pinterest. Focuses on helping leaders develop emotional intelligence, resilience, courage, and the ability to build high-trust teams whilst scaling companies.

About Lenny's Podcast: Interviews with world-class product leaders and growth experts to help listeners become better product leaders. Weekly episodes covering product management, growth, career development, and company building.

That’s a wrap.

As always, the journey doesn't end here!

Please share and let us know what you liked or want changing! 🚀👋

Alastair 🍽️.