Ganesh Datta
HostCTO & Co-founder of Cortex
Steve Evans
Former SVP of Engineering at Chegg
February 12, 2026
In This Episode
Cortex co-founder and CTO Ganesh Datta sits down with Steve Evans, the former SVP of engineering at Chegg. Steve shares his honest perspective on the "micro" in microservices and explains why making service creation too frictionless can accidentally lead to a massive organizational tax.
The discussion covers the transition from building for hypothetical future problems to focusing on actual business outcomes. Ganesh and Steve also dive into the "game of telephone" that often blocks context from reaching individual developers and discuss why engineering leaders should value qualitative sentiment as much as technical data.
You’ll learn
Engineering teams often over-build for ambiguous future problems that never actually arrive. Build for today's problems to avoid painting yourself into a corner with unnecessary infrastructure.
When the cost of a new service is nearly zero, developers will naturally choose to spin up new ones instead of digging into existing code. This creates a cognitive tax that slows down onboarding and makes working across teams feel impossible.
Technical metrics like release frequency are helpful for spotting anomalies, but they don't tell you if you're heading in the right direction. True productivity should be measured by business KPIs like payment success rates or accuracy of results.
Context often gets blocked as it trickles down from the C-suite to the individual contributor. Small roundtables with mixed groups are more effective than large all-hands meetings for identifying where that context is getting lost.
Leaders should look at the hard data but also pay close attention to the anecdotes and sentiment of their teams. If the metrics look good but the customers or engineers are unhappy, you've still got a problem to solve.
Quotes
"What I was railing against was the micro in microservices. We gave the team a hammer and everything became a nail."
Steve Evans
Former SVP of Engineering at Chegg
"Someone pulls up the service map in your observability platform and it makes the New York City subway system seem simple. You're sitting there unwinding the Christmas tree lights and trying to figure out how this thing works."
Steve Evans
Former SVP of Engineering at Chegg
"We've been measuring for a very long time how fast engineers run on a treadmill, not how far they're going."
Steve Evans
Former SVP of Engineering at Chegg
"This isn't IT summer camp. We're not here for kicks and giggles. We're here to produce business outcomes."
Steve Evans
Former SVP of Engineering at Chegg
Timestamps
01:08
Defining microservices as a trillion dollar mistake when they're over-engineered.
04:00
How zero-cost service creation creates an incentive model that backfires.
12:04
Identifying the macro tax of architectural complexity during critical incidents.
13:58
The cognitive tax that every developer pays when navigating a complex ecosystem.
19:34
Breaking down the difference between "miles per gallon" metrics and actual outcomes.
28:54
Why uptime is not the be-all and end-all for every business.
33:36
Managing the game of telephone between leadership and individual contributors.
41:48
Using small roundtables to identify and fix communication blockages.
46:28
Balancing quantitative data with qualitative sentiment to measure organizational health.
Other episodes
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The discussion covers the transition from a "Stockholm Syndrome" mindset where teams accept broken processes to a culture of reliability and security. Ganesh and Jeff also dive into the importance of incentives, the role of leadership in empowering teams, and why the most effective transformations start with identifying individual pain points rather than issuing top-down mandates.
January 29, 2026
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Fred also shares how Xero thinks about confidence scores for changes, why production readiness is a continuous journey rather than a one-time gate, and the importance of automating as much as possible to keep engineers focused on what matters most. The conversation also covers how AI coding assistance fits into production readiness, why security can't be separated from operational excellence, and Fred's best advice for engineering leaders just starting to build a production readiness program.
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Ganesh and Kaspar unpack why standardization doesn't kill creativity, the critical difference between "rigid paths" and "Golden Paths," and why treating your platform as a product is non-negotiable. They also discuss the emerging role of AI, arguing that AI agents are effectively a new class of "junior engineer" that makes robust platforms more essential than ever.
December 18, 2025
Kaspar von Grünberg
CEO and Co-founder
