Reading up on leadership
91 deep · digging since nov 19, 25
- The 33-year-old executive Satya Nadella is trusting to save Microsoft’s AI strategy
Microsoft is betting on rising executive Jacob Andreou to retool its Copilot AI product and regain competitiveness against rivals like OpenAI and Anthropic.
- Ask for no, don't ask for yes (2022)
Rather than asking for permission, offer colleagues a deadline to veto your planned action, which reduces their cognitive load and keeps projects moving.
- How Honda’s Pledge to Go All-Electric Unraveled
Honda's aggressive push to sell only electric vehicles by 2040 backfired when demand slowed, leading to its first-ever annual loss and internal calls for CEO Toshihiro Mibe to resign.
- Warsh Makes His Case With Jargon, and a Penchant for Detail
Warsh uses detailed jargon and a penchant for detail to outline a vision for change at the Federal Reserve during a press conference.
- https://x.com/cb_doge/status/2065431215545749608/video/1 (via @elonmusk)
Gwynne Shotwell delivers her full speech from NASDAQ, highlighting SpaceX’s achievements and future goals.
- The Steady Hand at SpaceX Is Not Elon Musk
Gwynne Shotwell serves as the stabilizing force at SpaceX, counterbalancing Elon Musk, as the company readies for a blockbuster IPO.
- For the Knicks’ Owner, a Title Might Finally Stop Some Boos
James Dolan, longtime Knicks owner, faces persistent boos from fans, and a championship may be the only way to change their perception.
- Elon Musk Laid Out 602 Goals. We Counted How Many He Hit. - The New York Times
A New York Times analysis found that of Elon Musk's 602 stated promises, only 19% were fulfilled on time, while 35% were never or late.
- What Is Airbnb For, Exactly?
Airbnb CEO Brian Chesky explains his founder-mode approach and rationale for expanding beyond rentals into hotels, car rentals, and groceries.
- Dropbox CEO Drew Houston to step down
Dropbox founder and CEO Drew Houston is stepping down after 19 years at the helm, moving to executive chairman, with co-CEO Ashraf Alkarmi continuing in the role.
- How SpaceX Is Structured to Favor Elon Musk
SpaceX's board structure and executive compensation disproportionately benefit Elon Musk over other shareholders, according to governance experts.
- Jeff Bezos Praises Trump’s Second Term as ‘More Mature’
Jeff Bezos publicly praised Donald Trump's second term as 'more mature' and denied adjusting Amazon or Post policies to win presidential favor.
- Harvard Faculty Vote to Approve Cap on A’s Per Course in Effort to Curb Grade Inflation - WSJ
Harvard faculty voted to approve a cap on the number of A's per course in an effort to curb grade inflation, despite sharp student backlash.
- How to Have a Difficult Conversation
Experts share effective step-by-step tools and techniques they use to navigate difficult conversations, making tough chats more manageable and productive.
- Meet Anthropic’s ‘Perfect Wingman’ for Its Race Against OpenAI - WSJ
Anthropic's CFO Krishna Rao seeks balance amid unprecedented growth, compute constraints, and intense competition with OpenAI.
- Meetings are forcing functions
Hacker News commenters sharply critique the idea that recurring meetings are effective forcing functions, with many citing them as bureaucratic time-wasters.
- OpenAI Wants to Go Public. First Sarah Friar Needs to Get It to Grow Up. - WSJ
OpenAI's CFO Sarah Friar is reining in Sam Altman's ambitious spending claims and imposing financial discipline as the company eyes a potential IPO.
- What ‘The Devil Wears Prada’ Taught Its Stars About Being a Boss
The cast and director of 'The Devil Wears Prada' reflect on leadership lessons from the film, the upcoming sequel, and which stars are actually kind in real life.
- Steiger Bean — AI Strategy for Executive Leaders
Steiger Bean is a CEO advisory firm co-founded by Celeste Bean and Jenni Steiger to help executives lead AI strategy and implementation.
- Tim Cook's Impeccable Timing
Tim Cook's CEO tenure at Apple is debated as operationally genius but lacking Steve Jobs-level innovation, with China and AI passivity as core critiques.
- John Ternus to become Apple CEO
Apple announces Tim Cook will become executive chairman and John Ternus will become CEO, effective September 1, 2026.
- Agentic Engineering Management
An exploration of applying AI agent loops to engineering management pillars—execution, team dynamics, personal development—assessing autonomy fitness and trust gradients for each.
- How Tim Cook’s Tech Uniform Helped Make Apple Trillions - The New York Times
Tim Cook's unassuming uniform of jeans and a polo shirt was an asset that helped Apple become a trillion-dollar company by projecting consistency and reliability after Steve Jobs.
- A Wish List for John Ternus, the Man Replacing Tim Cook as Apple’s CEO - The New York Times
John Ternus, Apple's hardware engineering chief, will replace Tim Cook as CEO of a highly profitable company that needs fresh ideas to sustain growth.
- Apple C.E.O.s Through the Years: From Michael Scott (Not That One) to John Ternus - The New York Times
A historical overview of Apple's CEOs from Michael Scott to John Ternus, detailing how each executive shaped the company's impact on technology.
- Nobody is coming to save your career
Hacker News commenters argue career growth is self-driven, not a manager's responsibility, while criticizing Amazon's lack of mentorship.
- Standoff With Iran Raises Fresh Doubts About Trump’s Freestyle Diplomacy - The New York Times
The standoff with Iran raises fresh doubts about President Trump's improvisational and uncoordinated diplomatic approach.
- LaGuardia Crash Tests New Port Authority Leader - The New York Times
The LaGuardia airport crash tested new Port Authority leader Kathryn Garcia, who consoled injured firefighters and managed delays across New York's three major airports.
- There are only two paths left for software
Software companies must either accelerate revenue growth by 10 points with new AI products or rebuild for 40%+ true operating margins, with no viable middle path.
- In Denmark’s Election, How Will the Woman Who Took On Trump Fare? - The New York Times
Prime Minister Mette Frederiksen, energized by the Greenland crisis, heads into Denmark’s election as a dominant yet possibly polarizing force.
- Exclusive | Mark Zuckerberg Is Building an AI Agent to Help Him Be CEO - WSJ
Mark Zuckerberg is building a personal AI agent to help him retrieve information faster and flatten decision-making layers at Meta.
- Staff complain that xAI is flailing because of constant upheaval
xAI staff complain that constant upheaval, co-founder departures, and Musk's hardcore demands are destroying morale and causing talent loss, despite aggressive expansion plans.
- How Jeff Bezos Upended The Washington Post - The New York Times
Jeff Bezos, dissatisfied with losses at The Washington Post, is pushing the newsroom to double productivity with half its budget.
- The Fall of Noma’s René Redzepi Reverberates in the Restaurant World - The New York Times
The closure of Noma sparks debate among chefs about the extent and nature of possible changes in restaurant kitchen culture and practices.
- 24 Hours With Nike’s C.E.O. as He Races to Win Back the Sports World - The New York Times
Nike CEO Elliott Hill travels globally to rebuild relationships with sports leagues and athletes to drive a turnaround for the company.
- Conductor Andris Nelsons Has Become a Cautionary Tale - The New York Times
Andris Nelsons’s abrupt departure from the Boston Symphony Orchestra was foreshadowed by his artistic decline, making him a cautionary tale for conductors.
- How Alberto Carvalho Became L.A.U.S.D. Superintendent Despite Scandals - The New York Times
Alberto Carvalho became L.A.U.S.D. superintendent amid scandals including an F.B.I. raid on his home and office, yet retained the job.
- Kristi Noem Survived Many Crises. Then She Crossed a Trump Red Line. - The New York Times
Kristi Noem's repeated political crises were tolerated until she violated a core loyalty expectation of President Trump, who then distanced himself from her.
- Something is afoot in the land of Qwen
Alibaba's Qwen team lead Junyang Lin and several other key researchers resigned, potentially losing the team behind the impressive open-weight Qwen 3.5 models.
- Trump Follows His Gut. His National Security Advisers Try to Keep Up. - The New York Times
Trump's rapid, instinct-driven decision-making process produces frequent contradictions and leaves his national security team unprepared for consequences.
- How Trump Decided to Go to War With Iran - The New York Times
President Trump's decision to take military action in Iran was driven by an Israeli leader's push to end diplomacy, with little opposition from advisers.
- Kickstarter’s C.E.O. on Running a Fully Remote Company With a Four-Day Workweek - The New York Times
Kickstarter CEO Everette Taylor explains how the company operates fully remote with a four-day workweek while managing both small projects and major corporate clients.
- Berkshire Hathaway Posts a Drop in Earnings in Buffett’s Last Year - The New York Times
Gregory Abel's first earnings report as Berkshire Hathaway CEO shows lower profits, mainly from insurance declines, using straightforward commentary instead of Warren Buffett's folksy style.
- What's Wrong With This Idea?
Asking "What's wrong with this idea?" invites honest critique, surfaces flaws early, and strengthens decision-making in technology teams.
- Watch: A Conversation With Anna Wintour and Her U.S. Vogue Successor, Chloe Malle - The New York Times
Anna Wintour and her U.S. Vogue successor Chloe Malle discuss the transition in their first joint interview, with Wintour urging people to move past comparisons.
- Management as AI superpower: Thriving in a world of agentic AI
An experimental UPenn class shows students building startups in four days with AI, arguing that management skills, not coding, are the superpower needed to thrive with agentic AI.
- forbes.com
Sam Altman's leadership of OpenAI and his aggressive bets on AI infrastructure and products position him as a transformative but controversial figure in technology.
- The Rise and Fall of South Korean First Lady Kim Keon Hee - The New York Times
South Korean First Lady Kim Keon Hee became the first former presidential spouse convicted on a criminal charge after her husband declared martial law.
- My time at Amazon, Part I - Becca Selah
A self-taught designer recounts her time at Amazon, detailing the rigid level system, the pressure to impress executives, and how motherhood forced her to confront the trade-offs of corporate ambition.
- Exclusive | The Messy Human Drama That Dealt a Blow to One of AI’s Hottest Startups - WSJ
Thinking Machines Lab CEO Mira Murati fired co-founder Barret Zoph after a tense meeting where Zoph and others threatened to leave unless he gained full technical control.
- a16z: The Power Brokers - Not Boring by Packy McCormick
a16z raised $15B in new funds, validating its strategy of building a scalable 'Firm' that sells power to portfolio companies, with Databricks as a prime example of its high-conviction, oversized bets approach.
- How a Puzzling 401(k) Plan Changed One Woman’s Life - The New York Times
Eryn Schultz, an H-E-B grocery store leader with an MBA, found her 401(k) plan wanting, triggering a slow pivot toward a career change.
- Elon Musk Relies on Gwynne Shotwell to Make SpaceX Soar - WSJ
The WSJ profiles Gwynne Shotwell's role managing crises like Musk's threat to decommission a spacecraft as SpaceX's IPO approaches.
- The Boss Who Hates Sick Day Requests - The New York Times
A boss's aversion to sick day requests highlights workplace tensions and the impossible demands placed on middle managers.
- Trump Addresses Venezuela, Greenland and Presidential Power in New York Times Interview - The New York Times
President Trump stated in a New York Times interview that he, not international law or treaties, would determine the limits of his presidential authority.
- Nicolai Tangen Manages Trillions of Dollars, but His Podcast Made Him Famous - The New York Times
Nicolai Tangen's podcast boosted his and Norway's $2.1 trillion oil fund's profile but embroiled it in a geopolitical tangle.
- Apple’s John Ternus Could Be Tim Cook’s Successor as CEO - The New York Times
Apple executive John Ternus, aged 50 with technical and organizational wins, may succeed CEO Tim Cook if he steps down.
- AddyOsmani.com - 21 Lessons From 14 Years at Google
Engineering success at Google depends more on navigating people, alignment, and ambiguity than on technical brilliance, according to 21 lessons from 14 years.
- Lessons from 14 years at Google
Lessons from 14 years at Google: novelty incurs debt, abstractions shift complexity, and clarity trumps cleverness.
- This week on How I AI: How Webflow's CPO built an AI chief of staff
Webflow's CPO built an AI chief of staff to run her week, using markdown files and disposable widgets for calendar delegation and meeting prep.
- Hasbro’s Secret Weapon for Training Its Next Leaders: A Board Game - WSJ
Hasbro uses an in-house board game, Toy Tycoon, to train up-and-coming leaders by role-playing as CEOs making strategic decisions.
- Katherine Maher of NPR Has Come Out on Top Despite Battles With Trump and the CPB - The New York Times
Katherine Maher's unyielding leadership in battles with Trump and the CPB has secured NPR's editorial independence despite internal friction.
- Miguel Carranza - My role as a founder CTO: Year Eight
RevenueCat's founder CTO recounts declining a near-$500M acquisition offer in 2024, choosing to raise $50M and build a multi-product company instead.
- Graphite Gets Bought By Cursor: Three Reflections from Six Years of Work [PMF didn’t happen right away; working IRL mattered; three founders, three distinct roles]
Graphite's acquisition by Cursor reflects lessons on finding product-market fit through iteration, the value of in-person work, and three co-founders staying united over six years.
- I'm a Tech Lead, and nobody listens to me. What should I do?
A tech lead who feels unheard should build influence through visible impact and trust rather than relying on hierarchical authority.
- The inside story of SpaceX’s historic rocket landing that changed launch forever - Ars Technica
Ten years after SpaceX's first Falcon 9 landing, the inside story details how the company overcame the CRS-7 launch failure and risky propellant densification to achieve rocket reuse.
- NASA finally—and we really do mean it this time—has a full-time leader - Ars Technica
Jared Isaacman is confirmed as NASA administrator, facing challenges of budget cuts, workforce reductions, and competition with China in returning humans to the Moon.
- Mozilla appoints new CEO Anthony Enzor-Demeo
HN commenters largely criticize Mozilla's new CEO, his MBA background, and the company's pivot to AI, arguing it undermines Firefox's only remaining differentiator of trust.
- Slate Q&A with CEO Chris Barman - YouTube
Slate CEO Chris Barman answers reservation holders' questions in a Q&A, providing detailed responses about the company's product and plans.
- How These Fortune 500 Leaders Navigate the Modern World
Fortune 500 leaders share strategies for navigating economic uncertainty, geopolitical tensions, and rapid technological change in 2025.
- From the DealBook Summit: Industry Leaders Share Their Insights - The New York Times
At the DealBook Summit lunch, leaders from technology, finance, education, and the arts shared key insights on critical questions of the day.
- DealBook Summit: Reckoning with the ‘New Normal’ - The New York Times
The DealBook Summit featured business leaders acknowledging that the Trump era has made the White House a central hub for corporate decision-making.
- Does the Job of C.E.O. or Private Investor Come First? Intel’s Chief Is Juggling That Question. - The New York Times
Intel CEO Lip-Bu Tan's dual role as a venture capitalist while leading a turnaround has raised questions about where his priorities lie.
- Meta’s New A.I. Superstars Are Chafing Against the Rest of the Company - The New York Times
Meta's AI elite clash with longtime Zuckerberg lieutenants, creating an us-versus-them tension inside the company.
- AI’s Next Challenge: Take the CEO’s Job - WSJ
Big-tech CEOs Pichai and Altman argue AI could soon handle executive roles, with Altman envisioning an AI-led OpenAI.
- Transparent leadership beats servant leadership
The HN commenters largely argue that the author's 'transparent leadership' is just a rebranding of true servant leadership, which already includes teaching and empowerment.
- Apple’s A.I. Chief, John Giannandrea, Is Retiring - The New York Times
Apple's AI chief John Giannandrea is retiring after the launch of a new Siri was postponed, reflecting Apple's struggles to keep pace with AI rivals.
- How to Attend Meetings
HN commenters largely agree with slide-deck advice on declining useless meetings but cite cultural resistance and lack of enforcement as barriers.
- Feedback doesn't scale
As organizations grow beyond 100 people, feedback becomes overwhelming noise because personal relationships don't scale, requiring structured systems like proxy relationships and working groups to replace direct trust.
- ‘In Triage Every Day’: A Beleaguered Speaker Says He’s Overwhelmed - The New York Times
Speaker Mike Johnson described being overwhelmed by the crushing demands of his role, joking his title is in name only.
- What a CTO should know about tech
A CTO must deeply understand technology capabilities and team strengths to make effective strategic decisions, drawing lessons from military theory.
- How the Coast Guard Revised Its Policy on Swastikas, Nooses and Bullying - The New York Times
The Department of Homeland Security revised Coast Guard policy to explicitly ban swastikas, nooses and bullying after public backlash.
- How evals drive the next chapter in AI for businesses
OpenAI advocates that "evals" — structured evaluation frameworks — are essential for businesses to turn vague AI goals into measurable, reliable outcomes.
- What Good Execution Looks Like - Yusuf Aytas
Good execution is defined by quiet, low-noise operations where clear direction, stable context, clear ownership, and trust enable teams to deliver without friction or management theater.
Takes
My favorite thing @om wrote was actually an interview with Brunello Cucinelli in 2015. And to this day, I think it’s the single best thing you can read on running a business. Better than any book, better than any article. Read it: https://om.co/2015/04/27/brunello-cucinelli-2/
@jasonfried
This is an email I sent earlier today to all employees at Coinbase: Team, Today I’ve made the difficult decision to reduce the size of Coinbase by ~14%. I want to walk you through why we're doing this now, what it means for those affected, and how this positions us for the future. Why now Two forces are converging at the same time. We need to be front footed to respond to both. First, the market. Coinbase is well-capitalized, has diversified revenue streams, and is well-positioned to weather any storm. Crypto is also on the verge of the next wave of adoption, with stablecoins, prediction markets, tokenization, and more taking off. However, our business is still volatile from quarter to quarter. While we've managed through that cyclicality many times before and come out stronger on the other side, we’re currently in a down market and need to adjust our cost structure now so that we emerge from this period leaner, faster, and more efficient for our next phase of growth. Second, AI is changing how we work. Over the past year, I’ve watched engineers use AI to ship in days what used to take a team weeks. Non-technical teams are now shipping production code and many of our workflows are being automated. The pace of what's possible with a small, focused team has changed dramatically, and it's accelerating every day. All of this has led us to an inflection point, not just for Coinbase, but for every company. The biggest risk now is not taking action. We are adjusting early and deliberately to rebuild Coinbase to be lean, fast, and AI-native. We need to return to the speed and focus of our startup founding, with AI at our core. What this means To get there, we are not just reducing headcount and cutting costs, we’re fundamentally changing how we operate: rebuilding Coinbase as an intelligence, with humans around the edge aligning it. What does this mean in practice? - Fewer layers, faster decisions: We are flattening our org structure to 5 layers max below CEO/COO. Layers slow things down and create coordination tax. The future is small, high context teams that can move quickly. Leaders will own much more, with as many as 15+ direct reports. Fewer layers also means a leaner cost structure that is built to perform through all market cycles. - No pure managers: Every leader at Coinbase must also be a strong and active individual contributor. Managers should be like player-coaches, getting their hands dirty alongside their teams. - AI-native pods: We’ll be concentrating around AI-native talent who can manage fleets of agents to drive outsized impact. We’ll also be experimenting with reduced pod sizes, including “one person teams” with engineers, designers, and product managers all in one role. In short: AI is bringing a profound shift in how companies operate, and we’re reshaping Coinbase to lead in this new era. This is a new way of working, and we need to leverage AI across every facet of our jobs. To those who are affected I know there are real people behind these decisions — talented colleagues who have poured themselves into this company and our mission. To those of you who will be leaving: thank you. You’ve helped build Coinbase into what it is today, and I am sincerely grateful for everything you've done. All impacted team members will receive an email to their personal account in the next hour with more information, and an invitation to meet with an HRBP and a senior leader in your organization. Coinbase system access has been removed today. I know this feels sudden and harsh, but it is the only responsible choice given our duty to protect customer information. To those affected, we will be providing a comprehensive package to support you through this transition. US employees will receive a minimum of 16 weeks base pay (plus 2 weeks per year worked), their next equity vest, and 6 months of COBRA. Employees on a work visa will get extra transition support. Those outside of the US will receive similar support, based on local factors and subject to any consultation requirements. Coinbase prides itself on talent density. Our employees are among the most talented people in the world, and I have no doubt that your skills and experience will be highly sought after as you pursue your next chapters. How we move forward To the team that is staying, I know this is a difficult day. We’re saying goodbye to colleagues and friends you've been in the trenches with. But here’s what I want you to know as we move forward together: Over the past 13 years, we have weathered four crypto winters, gone public, and built the most trusted platform in our industry. We’ve made it this far by making hard decisions and by always staying focused on our mission. This time will be no different – nothing has changed about the long term outlook of our company or industry. And most importantly, our mission has never been more important for the world. Increasing economic freedom requires a new financial system, and we’re building it. The Coinbase that emerges from this will be more capable than ever to achieve our mission. Brian
@brian_armstrong
yes we over-hired during covid because i incorrectly built 2 separate company structures (square & cash app) rather than 1, which we corrected mid 2024. but this misses all the complexity we took on through lending, banking, and BNPL. and that we’re now targeting $2M+ gross… https://t.co/uaKgTdzGob
@jack
Stripe's new frontpage shows the scope of their ambition. A ticker for percent of global GDP! This is not a gimmick. Patrick and John have always thought in these terms. pic.twitter.com/DD0qZPI3vS
@paulg
My conversation with Tobi Lütke (@tobi), co-founder and CEO of Shopify.0:00 Companies as Social Technology5:27 The Value of Reading Books: Cheat Codes for Life7:28 Post-IPO Crisis: Cosplaying as a CEO7:54 Competition vs Rivalry: The Power of Healthy Competition16:02 COVID… pic.twitter.com/WqXdq5EUm3
@davidsenra
I gave this talk to my team a few years ago and I find myself constantly referencing it - feels like it might be valuable for founders building their own company, and those that try to better understand our mindset and culture inside of Shopify pic.twitter.com/302T9EWlff
@tobi
Dropping another internal Context episode. @vlaurenlee and I talk about how she ascended Shopify from senior PM to leading all of product. Vanessa is brilliant. Worth a watch for any builders. pic.twitter.com/IQbZEEIsms
@tobi