Leadership

Testing out the new Claude Cowork. I asked it to go through every Lenny's Podcast episode and pull out the 10 most important themes and lessons for product builders. Then, the 10 most counterintuitive truths. I gave it access to a folder with 320 transcripts. First, it said "This is a substantial task - 320 podcast transcripts to analyze!" 15 minutes later... The 10 most important themes from Lenny's Podcast 1. Activation Is Everything — Slack's "2,000 messages" moment, Gamma's 30-second magic. Get users to value fast. 2. Storytelling as a Superpower — Compelling narratives align organizations better than documents. 3. Positioning Is Strategy, Not Marketing — April Dunford's 5-step framework that starts with competitive alternatives, not messaging. 4. Product Discovery Before Delivery — Teresa Torres' Opportunity Solution Trees and Marty Cagan's Four Risks framework. Talk to customers weekly, not quarterly. 5. Ruthless Prioritization — Shreyas Doshi's LNO Framework (Leverage/Neutral/Overhead) and focusing on opportunity cost over ROI. 6. AI is Transforming Product Development — Model maximalism, evals as core PM skill, CEOs becoming ICs again. 7. Empowered Teams vs. Feature Factories — Marty Cagan's distinction: give teams problems to solve, not features to build. 8. Build Your Operating System — Claire Hughes Johnson's framework for founding documents, operating cadence, and decision frameworks. 9. Pre-Mortems and Risk Anticipation — Shreyas Doshi's technique to surface failure modes before they happen. 10. Small Teams, Outsized Impact — Jason Fried's 2-person/6-week constraints, Shopify's pair programming culture. The 10 most counterintuitive truths: 1. Fear Gives Bad Advice—Do the Opposite — Whatever you're afraid to do (hard conversation, telling the board bad news) is exactly what you should do. 2. Adding Friction Can INCREASE Conversion — Adding personalization questions to signup improved Amplitude's conversion by 5%. 3. Fewer Features = More Value — The Walkman succeeded because Sony REMOVED recording. QuickBooks wins with half the features at double the price. 4. Adding People Makes You Slower (Absolutely) — Companies produce MORE total output after layoffs. Coordination overhead is the silent killer. 5. What Customers Say They Want Is Meaningless — 93% said they wanted energy-efficient homes. Nobody bought them. "Bitchin' ain't switchin'." 6. Goals Are Not Strategy—They're the Opposite — Richard Rumelt says confusing goals for strategy is the most common strategic error. OKRs are often just wish lists. 7. Don't A/B Test Your Big Bets — Instagram and Airbnb actively reject testing for transformational changes. You can't A/B test your way to greatness. 8. Your Gut IS Data — Intuition is compressed experiential learning that isn't statistically significant yet. Don't discount it. 9. Most PMs Are Overpaid and Unnecessary — Marty Cagan himself says feature teams don't need PMs. Nikita Bier calls PM "not real."

IndiGo (InterGlobe Aviation Ltd) CRISIS WASN’T IN THE SKIES. IT WAS IN THE LEADERSHIP CABIN. Three things stood out. One: Employees were left alone to face furious customers. No leader should ever let that happen. If you don’t stand by your people in a storm, don’t expect them to stand by your customers in the sun. Customer experience collapses the moment employees feel abandoned. Two: In any crisis, honesty is the only strategy that works. This time, the communication wasn’t transparent. When leaders hide the full picture, years of goodwill can disappear overnight. A crisis can earn trust, but only if you tell the truth. Three: The belief that “we are too big to be ignored” has ended more companies than competition ever has. Customers always have a choice. And if they don’t, they will create one. We shouldn’t watch the Indigo crisis like spectators. This is a reminder for every leader to build their own crisis blueprint. Because crises will come, when they do, your response becomes your reputation. There is more to business than profits. There are people, trust, and how you show up when it matters most.

Most organizations say they value honesty. But the moment disagreement shows up, many leaders get nervous. Here’s the truth: Healthy conflict isn’t a threat to unity — it’s the birthplace of clarity, innovation, and trust. When people stop disagreeing, ideas stop sharpening. Cultures get quiet. Toxicity grows in the silence. Leaders: if your team feels like there are things they can’t say, something is already broken. Invite honest disagreement. Model it. Celebrate it. That’s where progress and truth are found.

💡 Trust is what happens between the meetings. Not in the agenda. Not in the slides. It’s built in the tiny moments—the hallway chats, the “how’s your dad doing?” check-ins, the post-call laughs. That’s where culture quietly compounds. Remote teams don’t get those moments by accident; you have to engineer them. ✅ Create space for non-work huddles ✅ Check in just to say hi ✅ Celebrate people when no one’s asking you to Because trust isn’t a value on the wall. It’s the feeling people have when the meeting’s over.

This may be an unpopular opinion but.... the most important characteristics I look for in a leader are vulnerability, empathy, and intuition. Everything else is secondary. Why? ➡️ Hire a leader with empathy because if they can create a culture where your employees are not terrified to fail or make a mistake, that will allow them to be more innovative. At Spanx we had 'oops' meetings where we would go around and talk about a mistake we made that week. Employees (and leadership!) had to stand up and share their biggest screw-ups. It made it to where the fear of embarrassment didn't kill performance. ➡️ Hire a leader who's vulnerable and doesn't feel the need to put on a facade to be taken seriously. When I started Spanx, instead of talking at my customer, I wanted to talk to them. I made myself vulnerable, and I tried to apply that same logic to working with my employees. Vulnerability helps you connect with everyone. Your customers, your employees, even your critics! ➡️ Hire a leader who's in touch with their intuition. Do they know how to listen to their gut? Do they know when to throw out the data and the 'expert opinions'? The Spanx team and I did this in 2019 when picking the famous leather legging as our hero product of the year.... we had no proof that it would create a cult-following but we had a gut feeling and we trusted it. What are your top 3 things you look for in a leader? ⬇️

£322M in revenue. £120M cash in the bank. And still family-owned after 130 years. That’s Barbour. Most fashion brands chase growth at all costs. Barbour never has. A century-old and quietly spinning out £30m+ profit every year. The antithesis of the modern fashion playbook. → Revenue: £322m last year – compounding at 7% a year over 5 years → Gross margin: ~50%, among the strongest in fashion → Profit after tax of : £34m last year → Cash: £120m in the bank, balance sheet strength unrivalled They call themselves a Premium Niche. Jackets built to last decades, not seasons. So what’s the playbook? 1️⃣ Brand without dilution → Barbour does not discount — not online, not abroad → Instead they push sales via story-led branding 2️⃣ Heritage with a future → Same CEO for 25 years. Dame Margaret Barbour as Chair for 50. Jackets still made in South Shields since 1894 → Paired with reinvention: collabs with Erdem, Alexa Chung, Ganni. → Wax for Life, repairs and eco-materials - before Patagonia made it cool. 3️⃣ Global appeal → 130th anniversary campaign hit 1B impressions in 10 days across Asia → Early into China, Japan and the US - leveraging British heritage abroad → But adapted for local climates (eg. a 52-week summer range in the Gulf) Fashion loves disruption. Barbour proves discipline disrupts harder. If “boring” means £30M+ profit and £120M in cash… Maybe more brands should try being boring. -- I’m John - a CFO who loves brand and co-owner of Traction. Follow for insights on how - and why - brand building belongs on the balance sheet.

I was shadowing a coaching client in her leadership meeting when I watched this brilliant woman apologize six times in 30 minutes. 1. “Sorry, this might be off-topic, but..." 2. “I'm could be wrong, but what if we..." 3. “Sorry again, I know we're running short on time..." 4. “I don't want to step on anyone's toes, but..." 5. “This is just my opinion, but..." 6. “Sorry if I'm being too pushy..." Her ideas? They were game-changing. Every single one. Here's what I've learned after decades of coaching women leaders: Women are masterful at reading the room and keeping everyone comfortable. It's a superpower. But when we consistently prioritize others' comfort over our own voice, we rob ourselves, and our teams, of our full contribution. The alternative isn't to become aggressive or dismissive. It's to practice “gracious assertion": • Replace "Sorry to interrupt" with "I'd like to add to that" • Replace "This might be stupid, but..." with "Here's another perspective" • Replace "I hope this makes sense" with "Let me know what questions you have" • Replace "I don't want to step on toes" with "I have a different approach" • Replace "This is just my opinion" with "Based on my experience" • Replace "Sorry if I'm being pushy" with "I feel strongly about this because" But how do you know if you're hitting the right note? Ask yourself these three questions: • Am I stating my needs clearly while respecting others' perspectives? (Assertive) • Am I dismissing others' input or bulldozing through objections? (Aggressive) • Am I hinting at what I want instead of directly asking for it? (Passive-aggressive) You can be considerate AND confident. You can make space for others AND take up space yourself. Your comfort matters too. Your voice matters too. Your ideas matter too. And most importantly, YOU matter. @she.shines.inc #Womenleaders #Confidence #selfadvocacy

Stress isn’t always about the thing itself. It’s about our relationship to it. Two leaders can face the exact same challenge — a missed deadline, a difficult board meeting, a team conflict — yet their experience of stress is entirely different. Why? Stress often has less to do with the external event and more to do with the lens through which we view it. 👉 When we label something as unbearable, it grows heavier. 👉 When we approach it as a problem to be solved, it becomes manageable. 👉 When we see it as an opportunity to grow, it can even become empowering. This distinction matters because leaders carry tremendous weight. If everything feels like a “threat,” stress compounds. But if we learn to reframe — to shift our relationship to the pressure — we not only reduce stress, we increase our capacity to lead with clarity and resilience. As an executive coach, I work with clients on this every day. Here are a few practices that make a difference: ✅ Name it clearly. → Is it the situation itself that’s stressful, or the meaning you’ve attached to it? Naming the difference is the first step in reframing. ✅ Shift the narrative. → Instead of asking “Why is this happening to me?”, try “What is this asking of me as a leader?” ✅ Control the controllable. → Stress escalates when we fixate on what’s outside our power. Refocus on the small actions you can take. ✅ Build in recovery. → Even the strongest leaders need rituals that restore — whether that’s exercise, mindfulness, or simply 10 minutes of stillness. The goal isn’t to eliminate stress. The goal is to reshape our relationship to it so it serves us, rather than overwhelms us. Coaching can help; let's chat. Book Your Coaching Discovery Call Today  ↳ https://lnkd.in/eKi5cCce Enjoy this? ♻️ Repost it to your network and follow Joshua Miller for more tips on coaching, leadership, career + mindset. #executivecoaching #leadership #mentalhealth #coachingtips #wellness

Your success as a leader comes down to how well you set others up to succeed. And I’ve gotten this wrong more than once. When onboarding new leaders, I would give them a stack of docs, send them on a listening tour, and check in often. I assumed that was enough. It wasn’t. I gave them information—but not context. And context is what actually drives clarity, confidence, and results. I’ve since rethought my entire approach to onboarding leaders. This year, when two fantastic leaders joined our team, I did something different: spent a week on providing context. No shortcuts. We talked through: Our mission, strategy, and priorities What success looks like in their first 90 days, 6 months, and year What’s worked—and what hasn’t—in these roles before How we’ll share feedback and stay in sync The shift? Less “onboarding” as a task. More “transferring judgment.” We left with shared context. And here’s what’s interesting: the same thing applies when onboarding AI agents. You can’t just dump data into a system and hope it performs. AI needs context too—about your customers, your voice, your goals, and what “good” looks like. Whether you’re onboarding a new employee or a new AI teammate, the principle is the same: Context isn’t a nice-to-have. It’s the difference between getting started and getting results.

🥊 “Jingjin, have you ever considered that women are just inferior to men?” That was her opening line. The lady who challenged me was not a traditionalist in pearls. She was one of the top investment bankers of her time, closed billion-dollar deals, led global teams, the kind of woman whose voice dropped ten degrees when money was on the line. And she meant it. “Back in my day, if I had to hire, I’d always go for the man. No pregnancy leave. No PMS. No emotional volatility. Just less… liability.” And she doesn’t believe in what I do. Helping women lead from a place of wholeness. Because to her, wholeness is a luxury. Winning requires neutrality. And neutrality means: be less female and suck it up! I’ve heard versions of this many times, and too often, from high-performing women who "made it" by suppressing. But facts are: 🧠 There are no consistent brain differences between men and women that explain men’s “logic” or women’s “emotions.” 💥 Hormones impact everyone. Men’s testosterone drops when they nurture. Women’s cortisol rises in toxic workplaces, not because they’re weak, but because they’re sane. 📉 What we call “meritocracy” is often a reward system for those who can perform like they have no body, no children, no cycles. None of those are biologically male traits. They’re artifacts of a system built around male lives. So, if you're a woman who's bought into this logic, here are some counter-strategies: 🛠 1. Study Systems Like You Studied Deals Dissect the incentives, norms, and bias loops of your workplace the same way you’d break down a P&L. Don’t internalize what’s structural. 🧭 2. Redefine Strategic Strengths Stop mirroring alpha aggression to prove you belong. Deep listening, self-regulation, and nuance reading, these are leadership assets, not soft skills. Use them ruthlessly. 💬 3. Name It, Don’t Numb It If your hormones impact you one day a month, say so, but also say what it doesn’t mean: It doesn’t cancel out 29 days of clarity, strategy, and execution. 🪩 4. Build Your Own Meritocracy Start investing in spaces, networks, and cultures where your wholeness isn’t penalized. If none exist, build them. 🧱 5. Deconstruct Before You Self-Doubt When you catch yourself thinking “maybe I’m not built for this,” pause. Ask: Whose rules am I trying to win by? Who benefits when I question myself? This post isn’t about defending women. We don’t need defending. It’s about calling out the internalised metrics we still use to measure ourselves. 👊 And choosing to rewrite them. What’s the most 'rational' reason you’ve heard for why women are a liability?