Barry O’Reilly argues that artificial intelligence should sharpen leaders’ judgment rather than replace it, freeing them from administrative churn for deeper thinking and better decisions. The entrepreneur and author also warns that AI hype and content slop can shift unfinished work upward, demanding new standards of rigor, context and respect for colleagues’ time.

Molly Graham makes a case for career reinvention through calculated risk, beginner’s humility and a willingness to endure the emotional chaos of change. The new WorkLife host considers how small acts of courage can build resilience in a precarious job market and at midlife.

Product recruiter Chris Lee explains why job seekers should tailor their LinkedIn narratives to a specific target, treating the search as a test of candidate-market fit. He also walks through how recruiters scan profiles for stage, domain, seniority and hands-on AI experience before deciding whom to contact.

Semafor editor-in-chief Ben Smith makes the case for an anti-scale news business built on elite audiences, global events and aggressively independent reporting. He and Nilay Patel spar over creator economics, advisory boards, AI tools and whether audiences can still recognize journalism that refuses to be bought.

Google DeepMind’s leadership shakeup has sharpened doubts about whether the company can reclaim the AI frontier, even with its enormous resources, cloud business and consumer reach. Nilay Patel and Hayden Field weigh the costs of bureaucracy, brain drain and a widening split between long-term research and immediate commercial demands.

Microsoft’s CTO argues that the next phase of AI hinges less on raw model gains than on an open, secure agentic web capable of taking action across systems. He also defends makers’ right to choose between handcraft and automation, whether in code, woodworking or ceramics.

Charity Majors argues that AI’s boosters and skeptics are responding to real evidence: faster code generation on one side, worsening reliability and operational strain on the other. The Honeycomb co-founder makes the case for replacing faith in code review with production feedback loops, observability and stronger validation.

Molly Graham and AI-management educator Hilary Gridley consider whether generative tools can sharpen leadership or simply automate bad habits. Their conversation makes the case that clear judgment, explicit standards and accountability matter more as AI accelerates both thoughtful work and workplace slop.

Being "layered" at work—when a company hires a new boss above you or splits your role—can feel like a demotion even when it is a necessary response to growth. Molly Graham and former CrossFit CEO Don Faul map out how employees and leaders can handle the bruised egos, hard conversations, and potential opportunity with care.

Bluesky CEO Tony Schneider makes the case for a social network built less like a walled garden than an open web, with portable identities, interoperable apps and user-controlled moderation. He also sketches a business model based on commerce and referrals rather than advertising, while confronting the app’s political reputation and the challenge of broadening its audience.

Maggie Haberman joins Ezra Klein to trace Donald Trump’s second term as a government of improvisation, spectacle and unilateral power, where foreign policy, immigration crackdowns and self-dealing all orbit the president’s impulses. Their conversation argues that the administration’s chaos is less a coherent ideology than Trump reality: a White House shaped by flattery, grievance and a leader increasingly absorbed by monuments to himself.

Casey Newton talks with Granola co-founder Chris Pedregal about why AI meeting note takers have become indispensable office software, and what it means to turn workplace conversations into a permanent layer of machine-readable context. Their conversation circles the promise of better tools, the risks of surveillance, and the uneasy possibility that AI may make meetings easier without helping anyone work less.

A Checkr executive explains why some big-company operators thrive at startups while others wash out, tracing the answer to humility, hands-on experience, and a precise fit between what a company needs and what a leader actually knows how to build. The conversation widens into a playbook for moving upmarket into enterprise sales, designing incentives, using AI in production, and making decisions that scale without smothering a company in process.

Molly Graham talks with former Marine and Facebook executive Don Faul about what pressure strips away in leadership: ego, certainty and the illusion that authority is about being served. Drawing on combat, hypergrowth tech and personal setbacks, Faul makes the case for servant leadership, moral courage and the discipline to control how you show up when the stakes rise.

Altana CEO Evan Smith describes a world where tariffs, customs friction, and military choke points are forcing global trade to become more traceable, automated, and politically fraught. The conversation tracks how AI is remaking both border paperwork and software development while doing little to revive U.S. manufacturing jobs in the way tariff advocates promised.

Nilay Patel and Hayden Field size up Apple’s trade secret case against OpenAI as both a legal threat and a stress test for a company already juggling executive turnover, IPO pressure and an uncertain hardware strategy. Their conversation widens into a sharper question about AI’s future: whether OpenAI can turn consumer fascination into an actual market before enterprise rivals and courtroom battles define the field for it.

Every’s team breaks down how a new premium tier built around discounted AI tools produced the biggest subscription-revenue jump in the company’s history. The conversation doubles as a snapshot of how builders are using agents to automate the dull parts of work, orchestrate software stacks, and turn expensive experimentation into something more accessible.

Molly Graham talks with longtime TED steward Chris Anderson about the counterintuitive power of giving things away, from opening TED Talks to the internet to stepping aside as CEO and ultimately handing off TED itself. Their conversation treats letting go not as loss, but as a leadership practice that can unlock scale, trust and renewal.

After a layoff, product leader Eric Goehring rebuilt his search around referrals, careful storytelling and pointed reverse interviews, landing a new role in six weeks. Along the way, he argues that while AI can sharpen the work behind a search, hiring still lags badly in figuring out how to evaluate it.

Plaid COO Eric Sager describes how companies stay steady through shocks by treating acquisitions, pandemics and AI booms as milestones rather than identities, and by building a culture that prizes customers over short-term optics. He argues that organizational resilience comes from clear decision-making, spare capacity, frontline intimacy and leaders who reward behavior that strengthens the mission, not just the metrics.