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
How Thrive Market's SVP of Engineering thinks about reliability culture
In this episode of Braintrust, Cortex co-founder and CTO Ganesh Datta sits down with Randy Shoup, SVP of Engineering at Thrive Market. Randy shares lessons from his leadership roles across multiple companies and explains how measurement and transparency can help teams build stronger engineering cultures.
Randy and Ganesh chat about how fear can block progress, why recovery speed matters more than trying to prevent every failure, and how teams improve through steady, incremental gains. They also discuss a few practical ways to build trust around metrics so organizations can use visibility for learning instead of punishment.
February 26, 2026
Randy Shoup
SVP of Engineering at Thrive Market
Why great engineering teams don’t accept “normal” errors
Cortex co-founder and CTO Ganesh Datta sits down with Jeff Schnitter, a Solution Architect at Cortex. Jeff shares insights from his time as a Senior Principal Engineer at Workday, where he led developer experience and release engineering, to explore how organizations can successfully shift their internal culture.
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
Jeff Schnitter
Solution Architect at Cortex
Why production readiness at Xero starts with the customer, not the checklist
Cortex co-founder and CTO Ganesh Datta sits down with Fred Mare, Principal Engineer at Xero in Melbourne, Australia. They explore what production readiness really means, why it should be framed around customer impact rather than internal processes, and how to build a sustainable program without overwhelming your engineering teams.
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.
January 15, 2026
Fred Mare
Principal Engineer at Xero
