Stop Having All the Answers: An Executive Coach's Playbook for Tough Talks, Co-Founders and Energy

Lockett opens by saying she hopes listeners come away feeling that the human side of building a business is fun, impactful and achievable with simple tools. She illustrates with a client she has seen for ten years, who started as a frontline engineering manager at Coinbase with a dream of building a global community. He now runs a large community of creators and developers for Coinbase's Base app and, she says, is having more fun than ever.

The most common gap she sees, especially among technical leaders, is the assumption that they must have all the answers. People climb the ladder by being dependable and the smartest person in the room, but in a fast-scaling company they quickly have less context than the people around them. Lockett says that when you always advise, you train your team to bring you all their hard problems.

Coaching is a learnable alternative: shift into curiosity and help people solve their own problem. Advising is still right when an issue is urgent, when you know the answer you want driven, or when the person lacks the skill. Lenny compares this to the Harvard Business Review idea of the monkey on the back, where a leader's job is to keep the monkey with the person who owns it.

Lockett describes three levels of listening. At level one you are absorbed in your own inner dialogue and what the problem means for you. At level two you focus on the speaker and can repeat their words back. At level three, global listening, you also pick up body language, tone and context, and reflect back more than the speaker is aware of.

She demonstrates by asking Lenny what it is like to be a dad. He answers that it is the most amazing thing he has done but also challenging. She reflects back the squirm in his chair and his averted eyes, naming both high joy and the discomfort of sleep training and setting boundaries. Lenny says it felt good to be seen, and that it took less than a minute.

Lockett stresses that this does not require an hour-long coaching session with each person. Giving someone your full attention in the time you already spend, synthesising their words and mirroring the emotions you notice, builds connection. You can even check your guesses by asking whether you have it right.

A powerful question, Lockett says, comes from real curiosity, has no single right answer and opens up new options without leading the witness. She teaches the GROW model: goal, which asks what success looks like; reality, which asks where you are stuck and what you have tried; options, which asks what paths exist; and way forward, which asks what you will do next.

The questions need not come in order. If someone is clear on the outcome, spend your time on where they are stuck, and often saying the problem aloud leads them to their own breakthrough. Coaching assumes the person has the context, so it is the wrong tool if someone asks how to take a company public.

If you strongly disagree with where someone is heading, you can be honest and curious at once. Lockett suggests saying "help me understand how you came to that conclusion", then sharing your view openly while still letting them own the solution. In her talent work with CEOs she uses this to press on ideas like delaying a performance conversation for six months.

She gives the example of a client running an AI company who was also acting as head of product and had become the blocker on every decision. They set up squads, a biweekly product review and clear KPIs, and he moved from deciding everything to coaching with questions. Squads now move faster, and he has time to focus on product vision and strategy.

Lockett coaches Lenny on a real challenge: endless work. He describes a newsletter that began as a chill side project and grew, along with the podcast and a busy online community, into a constant stream of small asks, with a boulder always rolling behind him. She reflects that he loves the work yet wonders why it feels like fighting for his life.

Asked about his dream state, Lenny says it is roughly the same output with more free time to tinker with AI tools and spend with his wife and son. Lockett notices he describes tinkering both as spacious fun and as a way to stay ahead, and he agrees both are true. He admits that when he gains free time he fills it with new commitments, even after setting rules to refuse talks and events.

For options, Lenny lists publishing less often, having already cut the newsletter to two to four posts a month, plus delegating more and sharpening his no policy. His next step is to skip a newsletter in two weeks and revisit what he says yes to. Lockett adds that the more resonant the end state, the easier near-term discipline becomes, and she urges a full-bodied yes to what you want.

Afterwards Lockett notes that people are far more bought in when coached than told, and that the same questions work on technical, urgent topics. She adds that great leaders ask whether someone wants advice or space to think. Lenny agrees that unsolicited advice rarely lands.

Lockett recalls running a coaching program for roughly 50 top technology executives at Stripe, whose engagement scores showed how exhausted creative, committed leaders had become. The people who stayed energized, she says, were those spending most of their time in their gifts, the things they are naturally good at and love doing. She aims for 80 percent, accepting that some 20 percent will always be unloved logistics.

Founders often drift out of their strengths without noticing, such as a technical founder who solves a problem they are obsessed with for three years and then finds themselves managing a board and a team. To spot this, she suggests listing each night for two weeks the five things that gave you the most energy and the five that drained you. Patterns reveal a slow leak in your gas tank.

Lenny says he did something similar when leaving his job and found advising calls depleting but writing energizing, so he followed that. Lockett offers other methods: ask five to 10 people what shows up when you walk into a room, or review your calendar for what you look forward to and dread. She says designing life around your gifts takes intention and risk.

Telling the people around you matters. When Lockett worked at Stripe she explained to her boss that she planned to become a coach, and was then given talent retention work that fit that path. Founders can hire around their weaknesses, for example visionaries who hate managing teams pairing with a COO.

Responding to Lenny's point that most people have jobs and responsibilities, Lockett says that people executing well can ask for roles that fit their strengths, since employers want to know what will keep them for five years. That may mean moving horizontally rather than up the ladder, which took her several risks and some uncomfortable jobs. Sometimes leaders hire a chief of staff or build teams with complementary strengths.

Her own story illustrates this. Ten years ago at a small company called Remind she moved from running user research into a product manager role and won over a skeptical group of senior engineers, yet she lay awake agonising over design decisions. A colleague told her that her gift was not product strategy but motivating teams and influencing executives, and although initially offended she knew he was right, and trained as a coach.

She says it is no one else's job to help you live in your gifts: a manager's job is to help you perform in the role you were hired for, while navigating your career is on you. Lenny cites founders who structured around their weaknesses, including a president hired to run operations and a CTO who made a rule of having no reports. Lockett cautions that you must still make sure people get managed.

Her advice is to start small. You do not need to quit your job; skip optional draining events, take a 30-minute walk between depleting meetings, or read before bed. Lenny says he has started reading a physical book for 30 minutes before sleep and finds it joyful.

Lockett loves working with co-founders because their core values surface when they meet someone else's. She compares it to a marriage that people hesitate to discuss with friends or their board, and notes the commonly cited statistic that 65 percent of startups fail because of co-founder conflict. A healthy relationship, she says, starts with self-awareness of what each person brings and how they are experienced.

She suggests tools such as the Enneagram, or simply telling each other your strengths and weaknesses and how you will cover gaps neither of you fills. She describes a typical tension between a skeptical, fact-seeking CTO and a vision-selling CEO, a dance between skepticism and optimism. Knowing the dance keeps you from stepping on each other's toes blindly.

Second, make conscious commitments, which she calls co-founder vows, and renew them like a couple needs a date night. Schedule biweekly dinners, regular lunches or quarterly in-person check-ins to ask how it is working and what has gone unsaid. She describes this as getting off the dance floor and onto the balcony, and has co-written a check-in guide with First Round.

When founders come in frustrated, she says, they usually still care about the business and remember loving the partnership. She describes a PR duo whose roles had pulled them apart, who used a 360 review and open conversation to name the current state, and who left recommitted with a weekly virtual meeting and quarterly in-person time. In another case, a day together made clear that one founder would leave, which she counts as success because clarity lets you stay or step out lovingly.

Lockett says people often enter a conflict armored to prove the other person wrong, when the real goal is mutual understanding. She teaches Marshall Rosenberg's nonviolent communication in four steps. First, state a factual observation, such as not being invited to the last three sprint planning meetings. Second, share your feelings without blame, such as feeling anxious or confused.

Third, name the universal need behind the feeling, such as clarity, collaboration or connection. Fourth, make a small, easy request, such as being included as optional or sent the roadmap afterward. The other person need not agree and may counter-propose; the point is that they understand you without feeling defensive.

She links this to the Stanford business school course known as Touchy Feely, where staying on your side of the net means sharing emotions and needs without blame or assumption. She also notes that a feeling is an emotion word, so phrases like "I feel like you're being a jerk" are really judgments. Lenny says the reframe that the goal is understanding rather than convincing blew his mind.

Lockett adds that ignoring feelings does not make them go away: they bubble up and drive behaviour unconsciously, so professionals should acknowledge that they have feelings. When the other person shares a different perspective, you can ask whether they are open to hearing your side, and vulnerability tends to invite vulnerability in return.

Lockett says conflict has poor marketing: we want to run from it, yet when we feel ambivalent or in conflict, something we care about is at stake. She asks leaders to see the difficulty as a sign there is something to learn and a skill to build. She believes the quality of our relationships determines the quality of our lives, and that without conflict you cannot have healthy ones.

Second, she says we always contribute to the conflict, however insane the other person seems. Entering with humility and curiosity matters, because no framework can rescue someone arriving rigid and full of blame. She cites the idea of taking 100 percent responsibility, rather than playing victim or hero, and Lenny recalls Jerry Colonna's question about how you are complicit in creating conditions you say you don't want.

She gives an example of a CEO whose co-founder kept undercutting his decisions. Using the nonviolent communication steps, he learned the co-founder was frustrated that he spent time selling instead of on product vision. Lockett distinguishes this from burnout advice: you should not grind through depleting work, but when you avoid an interpersonal issue, it is because you care.

For talent decisions she recommends the Stripe question: would you enthusiastically rehire this person for the same role? A no does not mean fire them, she says; it means act, whether by a conversation, a performance plan or a different role. She notes leadership teams outgrow their roles as a company scales, and that talent and the environment you build for it are everything beyond product-market fit and timing.

Lockett says companies complicate alignment so that vision, strategy, goals and values live in different places, and employees could not easily name the top three priorities. She likes the one-page plan, which she adapted from Alpine Investors' people-first operating rhythm, because it simplifies. Columns run from vision and values to strategic intentions and KPIs, then annual goals and quarterly goals.

She says Alpine has collected data suggesting portfolio companies that use the rhythm see higher returns, and she works with some of their CEOs. The benefits she sees are clarity, alignment and more connection, because how the plan is created and reviewed matters as much as the document. She offers to share a template.

The rhythm includes kicking off the year with the plan and meeting each quarter to reflect on what worked and what didn't. She likes asking "what's an inconvenient truth?" to surface what nobody has time to discuss. Like co-founders, executive teams need to get onto the balcony and have some spacious time to work on the business.

Lockett uses AI in three ways. Granola takes notes during sessions so she can be fully present, and a folder per client lets her spot patterns over time. She uses ChatGPT to brainstorm fresh ideas for the eight retreats a year she runs for a women's organization.

She is also experimenting with an AI companion for clients between sessions. It would hold their development plan, her frameworks and the session notes, and give tactical help such as how to approach an anxious team meeting. She sees personal coaching as still essential for vision and deep behaviour change, with AI covering tactics.

Her closing message is that the world is getting lonelier and building businesses is a human endeavour. She likes the AI boom but urges leaders to bring people together and overcome the default of blind grind and loneliness. In the lightning round she recommends *The 15 Commitments of Conscious Leaders* and *Designing Your Life*, and shares a Joseph Campbell line about making your own path with every step.