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When AI Metrics Go Sideways

Neela Deshpande
Neela Deshpande
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Roundtable: The AI Productivity Paradox: Why Some Teams Gain 30% While Others Lose 20%

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This is a special episode, highlighting a session from ELC Annual 2025! Bill Coughran (Partner @ Sequoia Capital & former SVP of Engineering @ Google) and Bret Reckard (Talent Partner @ The General Partnership) deconstruct the evolving role of engineering leadership in an era dominated by AI hype. Bill is a legendary leader who joined Google right after the .com bubble and has seen every major industry shift since. Drawing on his experience scaling Google and advising world-class startups, Bill shares why the best leaders are "catastrophic thinkers," how to balance servant leadership with the need for decisive action, and why AI is forcing every leader to return to their technical roots. Plus they cover enduring companies and real value capture in the AI era, the nuances of organizational design, the "apprentice model" for mentorship and the dangers of over-layered hierarchies that stifle speed. Bill also provides a candid look at leadership transitions, offering a tactical guide for those moving from Big Tech to early-stage startups.
This is a special episode, highlighting a session from ELC Annual 2025! OpenAI evolved from a pure research lab into the fastest-growing product in history, scaling from 100 million to 700 million weekly users in record time. In this episode, we deconstruct the organizational design choices and cultural bets that enabled this unprecedented velocity. We explore what it means to hire "extreme generalists," how AI-native interns are redefining productivity, and the real-time trade-offs made during the world's largest product launches. Featuring Sulman Choudhry (Head of ChatGPT Engineering) and Samir Ahmed (Technical Lead), moderated by Lawrence Bruhmeller (Eng Management @ Sigma).
In this episode, Brian Balfour (Founder & CEO @ Reforge) deconstructs the two core, interconnected challenges leaders face in the AI age: deciding what to build and evolving the Engineering, Product, Design workflow to deliver it. We cover why you should avoid “the local maxima trap” and siphon off "skunkworks" teams to take high-risk, AI-native bets. Brian provides the blueprint for the "Great Distribution Shift," detailing how to reshape your product from the ground up to avoid being left behind as platforms close, and how to emerge as a winner in the new AI landscape. Plus, learn how to rethink what to build, avoid commoditization, compress product discovery from weeks to hours, scale feature variations & prototypes, evolve products to solve harder classes of problems and shift specialist roles from "inboxes" to system builders.
In this episode, Daniel Lereya (Chief Product and Technology Officer @ Monday.com) shares how they are evolving their engineering roles from developers to builders & system designers, where the lines between product, engineering, and design are intentionally blurred, and developers manage AI Agents as team members, tackling an ever-expanding list of projects. We explore the shift from "developer" to "system designer" and why managing AI agents requires the same skills as managing people. Plus, a case study where the Monday.com team leveraged AI agents to decompose a monolith, autonomously manage the project board and assign strategic / high-risk tasks to humans.
During this session, we discussed the importance of aligning technical strategy with business goals, the realistic impact of AI on productivity, and the need for cross-functional collaboration to keep roadmaps both flexible and realistic.
# Leadership
# Engineering Leadership
# Roundtable
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This is a special episode, highlighting a session from ELC Annual 2025! The true promise of AI isn’t in replicating human intelligence. It’s in developing entirely new forms of non-human intelligence that perceive and understand the world in fundamentally different ways. Jamie Lien (Co-Founder and Chief Scientist @ Archetype AI) and Rashi Agarwal (Head of AI Engineering @ GoodLeap) explore the emergence of "Physical AI" - machines that sense the world through modalities beyond human biology to form internal representations free from our biases and then translate that understanding back to us in human terms.
In an era where AI delivers answers instantly, leadership is shifting from output to awareness. This article explores how curiosity, clarity, and connection become essential skills for engineering leaders who want to stay grounded in their own judgment—rather than outsourcing confidence to the machine.
# AI
# Leadership
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Michael Woodley
Michael Woodley · Dec 1st, 2025
Baaaaaaa.🐑 You’ve heard it before — the sound of teams moving fast but not forward. In the race toward AI, most leaders follow trends instead of realizing purpose.
# AI
# Culture
# Building Team Culture
# Leadership
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Ruslan Belkin (Head of Platform Engineering @ Inflection AI) joins us to deconstruct fundamental shifts in engineering leadership. We explore the future of user interfaces, his “sci-fi” approach to establish & test product vision, & how to leverage “investor decks” for better decision-making and project validation. Ruslan also dives into the complexities of building emotional intelligence into AI systems, cultivating an outcome-oriented engineering culture & avoiding process traps. Plus, we discuss how to keep up with the velocity of change (including when new research necessitates a major pivot), synthetic data & the future of data as a defensibility strategy, & why agent reliability is the massive opportunity ahead. 
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