What is leadership in the AI Era? w/ Bill Coughran & Bret Reckard #243
The Engineering Leadership Podcast
Transitioning from Big Tech to Startups
Bill recommends new leaders do coding work, learn the codebase, and avoid imposing big-company playbooks at startups.
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.
ABOUT BILL COUGHRAN
Bill Coughran works as a founders' coach and partner at Sequoia Capital to help build spectacular technology-centric companies. Previously, Bill was Senior Vice President of Engineering at Google with oversight of Chrome, YouTube, maps, google.com, underlying infrastructure systems, and security.
ABOUT BRET RECKARD
Bret Reckard is Talent Partner at The General Partnership (TheGP), a hands-on venture firm working alongside ambitious founders in talent, engineering, go-to-market, and product. He leads TheGP’s Talent vertical, matching foundational leaders, early engineers, and key specialists across the portfolio. Before this role, Bret spent over a decade at Sequoia Capital leading Talent and Network, where he helped hundreds of founders at companies like Stripe, Confluent, Retool and DoorDash build their early teams.
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SHOW NOTES:
- Introduction and Bill Coughran's background at Sequoia and Google (1:36)
- Hiring pitfalls and the biggest mistakes made as a leader (3:49)
- Managing crises: Acting as a dictator during the 2010 Google hack (5:25)
- Building for the AI world without chasing "shiny objects" (7:09)
- Developing context: How to learn AI without relying on LLM summaries (9:02)
- Identifying enduring companies and real value capture in the AI era (10:53)
- The debate on coding assistants and the future of junior engineering talent (13:23)
- Transitions: Making the leap from large organizations to early-stage startups (15:59)
- Staying curious and finding excitement in the next professional challenge (18:23)
LINKS AND RESOURCES
This episode wouldn’t have been possible without the help of our incredible production team:
Patrick Gallagher - Producer & Co-Host
Jerry Li - Co-Host
Noah Olberding - Associate Producer, Audio & Video Editor https://www.linkedin.com/in/noah-olberding/
Dan Overheim - Audio Engineer, Dan’s also an avid 3D printer - https://www.bnd3d.com/
Ellie Coggins Angus - Copywriter, Check out her other work at https://elliecoggins.com/about/
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