Leaders LoopThe Data Behind College Football’s New Era
Ron Yurko, director of the Carnegie Mellon Sports Analytics Center, explains how data is reshaping the Heisman race, college football forecasting, and sports betting. … Read More
Reading List
The Leadership Reading List
We don't write everything worth reading. This is where we collect the best leadership and business writing from other publications and blogs, so you don't have to go looking for it.
AI Safety Has Reached a Critical Point
Kevin Werbach, professor of legal studies and business ethics at the Wharton School, explains the growing risks of artificial intelligence and why government regulation may be necessary to keep frontier AI in check. … Read More
When Compliance Workarounds Backfire
John Holcroft/Ikon Images In 2021, Barcelona-based delivery platform Glovo was faced with a law that threatened its business model. Spain had passed the Rider Law, which introduced a presumption of employment when a digital platform organizes, directs, or controls couriers’ work, including through algorithmic management. Glovo came up with what seemed like a clever fix […]
How do you like them apples?
In October, the apples in New England are some of the best in the world. Alas, the apples in this bowl are nine months old and from 3000 miles away. I found them sitting in a forlorn corner of a hotel gym in Cape Cod. Why source lousy apples? Because they’re not being hired to […]
Building a second-wave AI business
A very long rant, riffing on the opportunity for bootstrapped startups who seek to create value using AI. I wrote it a while ago, thought it was too long, but in arguing with an AI today (everyone needs a hobby) I realized it was worth sharing: Most AI success stories to date are about cost […]
The Real Reasons Why Digital Projects Fail
Danae Diaz/Ikon Images It’s a familiar scenario: An organization implements digital tools intended to improve a particular process but fails to obtain the desired result. Employees who are meant to use them complain that the tools don’t solve the problem or that they add inefficiencies. Managers who investigate problems with the tools chalk the failure […]
Lobby expertise
Someone who has seen a lot of movies but has never made one has a certain kind of knowledge. The same is true for clients, patients and students. They haven’t solved a problem, healed a patient or taught a class, but they’ve seen it done. They might have something helpful to add. Or they might […]
How to Respond When People Throw Wrenches During Change
CHANGE initiatives rarely fail because of flawed strategies or poor execution. They fail because of human behavior: what people do when they feel threatened or at risk of losing status, control, or relevance. A senior leader withholds resources from another team. A project team member hoards information about transition status. Each move undermines the initiative's success. When combined with othe
🎙️ How I AI: 8 real Jev use cases + How OpenAI uses ChatGPT Sites (live at DevDay!) + Claire’s DevDay recap
Your weekly listens from How I AI, part of the Lenny’s Podcast Network
AI’s Impact on Financial Services
Jeremy Siegel and Jeremy Schwartz discuss how artificial intelligence is transforming financial services, from investment research and financial advice to productivity, innovation, and the future of the industry. … Read More
How OpenAI uses ChatGPT Sites (live at DevDay!) | Kath Korevec (Product Lead)
Watch now (36 mins) | 🎙️ Kath Korevec demos ChatGPT Sites live at OpenAI DevDay, showing how to turn Slack, Notion, and calendar data into internal tools that adapt to each person on your team
Rehearsal Intelligence: Using Digital Twins for Crisis Readiness
Carolyn Geason-Beissel/MIT SMR | Getty Images In July 2024, the cybersecurity software company CrowdStrike released a defective content configuration update. In the ensuing 78 minutes, before a patch was deployed, IT systems worldwide crashed. Microsoft estimated that 8.5 million Windows devices were affected. As blue screens of death cascaded across the globe, airlines grounded fleets, […]
Create a handoff doc
Imagine if your job required you to maintain an updated handoff doc, something the boss could give to a new hire that would let them immediately get caught up on the work. All the file names, locations, assumptions, choices, dilemmas and contacts, organized and ready to go. Creating something like this would be annoying and […]
OpenAI’s Head of ChatGPT: We’re entering a new era of AI (again) | Tibo Sottiaux
Listen now (37 mins) | Tibo Sottiaux on why Dots is OpenAI’s biggest bet, why agents will dominate internet traffic, and what builders are still getting wrong
Getting critical
I’d heard a lot about critical theory but didn’t really understand what was being talked about. The Frankfurt School of the 1930s wasn’t really a school. It was philosophers and academics who were arguing with each other about how the world actually works — and about why people keep accepting arrangements that hurt them. And […]
🧠Community Wisdom: Getting value from personal AI agents without handing over your inbox, the ego threat of going from IC to manager, uncommon perks to negotiate for, and more
A roundup of community insights covering how to leverage AI assistants for productivity while maintaining privacy boundaries, the psychological adjustment challenges when transitioning from individual contributor to management, and lesser-known workplace benefits worth advocating for during negotiations.
Uniformity
Consistency costs extra. If you want to buy machine screws or widgets that are exactly the same to five decimal points, you’ll pay a premium for that. In exchange, you’ll get parts that are precisely as expected, making assembly more reliable. Mechanization’s productivity and our fear of fear have driven us to do this with […]
The Hidden Cost of Competition in the Workplace
Henning Piezunka, Wharton associate professor of management, explores how rivalry motivates individual performance while potentially undermining team success. … Read More
Modern vanity
“Vanity” has the same root as “in vain.” Emptiness. Staring at the mirror, focusing on our appearance. It’s an empty pursuit of a not-very-worthwhile goal. But modern vanity is amplified. Culture hooked the toxic emotion of shame to vanity. Now, instead of a chance to be seen and admired, vanity is mostly about avoiding the […]
Leading Thoughts for October 1, 2026
IDEAS shared have the power to expand perspectives, change thinking, and move lives. Here are two ideas for the curious mind to engage with: I. Brady, Kliman, and Smith on seeing the full story: "We feel strongly that empathy and humility aren’t distractions from value creation; they’re the drivers of value creation. In fact, they’re essential if we want to lead difference-filled teams that solve