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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.

Building Self-Trust in the Age of AI: Leading with Curiosity, Clarity, and Connection

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.

Sheep and Shepherds

Beyond Velocity: 5 Surprising Truths About Measuring AI's Impact in Engineering

AI as an Organizational Mirror: What It Reveals — And Requires

At ELC 2025, what began as a discussion on defining outcome-oriented metrics for AI features turned into something more revealing: a shared struggle among engineering leaders to measure the real impact of AI-assisted work. This piece explores why teams often mistake productivity spikes for progress, the missing link between activity and outcome, and how to bridge that gap with metrics that actually matter.

When AI Metrics Go Sideways

Engineering Leadership in an AI-First Company Culture

Wade Chambers discusses how to learn anything by applying “conscious growth” and neuroplasticity to your career. You’ll learn how to get unstuck, and move your career forward. Plus Wade also shares stories about his early failures as an engineering manager, and what he wished he knew when he first became a manager. 

Conscious Career Growth (part 1)

In this episode, we discuss frameworks & strategies for building a “startup-within-a-startup” with Heidi Williams, Head of Engineering for Grammarly Business @ Grammarly! She shares stories about her leadership style while revealing the benefits of & considerations for creating a startup-within-a-startup, sourcing ideas & hosting knowledge-sharing meetings, identifying adjacencies in your user base, communicating challenges between individuals & teams, developing leading indicators, and more.

Building a startup-within-a-startup

Will Larson CTO @ Calm shares with us how to focus your time on what actually matters. You’ll hear about many of the common traps engineering leaders fall into and his frameworks to help you better target your time to focus on long-term, high-impact work.

Spend Time On What Matters

Albert Strasheim, CTO & SVP of Engineering @ Rippling, joins us to share the riveting story of how Rippling’s leadership navigated the recent collapse of Silicon Valley Bank. He reveals what was at stake for his company & the hundreds of millions of dollars at stake for customers & their employees, how Rippling’s core values influenced their critical decision-making, tips for communicating with clarity both internally & externally, and tactics that allowed the team to respond with precision during crisis. Additionally, Albert shares the pre-crisis strategies, habits & systems he is most thankful for that helped Rippling leadership respond successfully throughout this critical period.

Rippling's Response to the SVB Collapse: A Story of Leadership, Crisis Management, Clarity and Communication

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Leadership Blogs

.css-4atpvc-StyledLink:hover *{color:var(--theme-color-primary, #04B17D);}Building Self-Trust in the Age of AI: Leading with Curiosity, Clarity, and Connection

Building Self-Trust in the Age of AI: Leading with Curiosity, Clarity, and Connection