Culture, Quality, and Tech Debt: Lessons from the Front Lines with Greg Conklin

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by special guest Greg Conklin for a candid and insightful conversation on what it takes to build high-performing engineering teams.

Drawing from their shared time at the telemedicine startup 98point6, the trio unpacks hard-earned lessons around tech debt, operational excellence, and culture-first leadership. Topics include:

• Why setting guardrails for quality, performance, and reliability early pays dividends later.
• The real value of postmortems and RCA meetings (and how to make them stick).
• How overly strong culture filters can unintentionally suppress bravery and dissent.
• What startups should prioritize in their first few quarters to avoid painful rework.

Whether you're scaling an early-stage team or trying to fix systemic issues in a mature org, this episode delivers practical frameworks and honest reflection from leaders who've been there.

• 00:00 Introduction and Welcome
• 00:46 Guest Introduction: Greg Conklin
• 02:05 Revisiting 98.6: Lessons Learned
• 03:27 Empowerment and Quality at 98.6
• 05:32 Challenges in Engineering Management
• 10:46 Operational Excellence and Technical Debt
• 24:25 Dropbox Postmortem Insights
• 27:14 Blameless vs. Egoless Retrospectives
• 30:51 Setting Early Standards in Startups
• 35:11 Challenges in Test Automation
• 38:49 Local Development and Ephemeral Environments
• 44:33 Concluding Thoughts on Engineering Leadership
• 47:15 Podcast Outro and Credits

Resources:

• How Many CTOs Pod: https://howmanyctospod.com
• Scott Porad: https://www.linkedin.com/in/scottporad/
• Brad Hefta-Gaub: https://www.linkedin.com/in/bradheftagaub/
• Greg Conklin: https://www.linkedin.com/in/gregoryconklin/
• Greg's Blog: https://gregconklin.com/

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