Engineering Leadership
Rewrites are an organizational failure more often than a technical one. These episodes are about the people side.
A rewrite produces almost no external evidence of progress for a long time, and leaders respond to that silence with oversight: longer status reports, more frequent reviews, more stakeholders in the room. To the team it reads as micromanagement; to the leader it is managing risk with nothing to go on. Both readings are right, and the supervision itself slows the work down further.
These conversations cover the ground underneath that: culture, autonomy, hiring, morale, running organizational change, and teaching engineers to describe technical friction in terms the rest of the business can act on.
54 episodes · browse the full archive
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20:51
TheseusShipping Outside of the Tech Stack (Ep. 160)
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11:37
Episode 151: Celebrating Wins During Constant Iteration
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38:24
Episode 147: Managing Organizational Change ft. Sophia Rosa
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27:46
Episode 146: How AI is Reshaping Careers and Workflows
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10:48
Episode 143: Tactics to Obscure (Parody)
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23:50
Episode 142: Are You Ready to Scale? A Local Case Study
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14:14
Episode 136: Key Questions to Ask When Navigating Your Career
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49:57
Episode 135: Is Changing an ERP System a Rewrite? ft. Sophia Rosa
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17:40
Episode 129: Credit Where Credit Is Due
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16:04
Episode 128: Revisiting An Old Story With Our Current Experience
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28:59
Episode 127: The Pains Caused by Differing Abstractions
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20:16
Episode 125: Navigating Risky Software Setups
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29:30
Episode 124: Treating Communication Gaps Like Tech Debt ft. Austen Tucker
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27:10
Episode 122: Providing Constructive Feedback
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20:33
Episode 120: Bad Testing & Release Practices Are Cultural Problems, Not Technical Problems
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20:14
Episode 117: How to Make Incremental Changes Visible
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36:36
Episode 115: [CI/CD] Beautiful Feedback Loops with guest Spriha Tucker
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19:21
Episode 112: The Impact & Cost of Hidden Business Rules
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13:34
Episode 111: The Social Aspects of a Failed Rewrite
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20:05
Episode 109: Conway's Law and Software Quality
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16:07
Episode 108: Consolidating Tech Stacks - Is It Worth It?
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33:44
Episode 104: An Infrastructure Rewrite Story with Guest Paul Stack
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17:32
Episode 97: Fulfilling Friday - A Tattoo Scam?
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17:03
Episode 92: A Framework for Prioritizing Tech Debt ft. Dustin Rea
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23:56
Episode 88: Creating a Culture of Continuous Improvement with Guest Erik Enge
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8:28
Episode 86: Annual Reminder - Prune Your Meetings
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19:38
Episode 84: The Impact of AI on Interviewing
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33:33
Episode 83: The Impact of AI on Recruiting
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12:28
Episode 80: What is "De-Risking"?
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18:29
Episode 79: The Toxicity of "Certainty"
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12:51
Episode 71: Are Ignorable Errors Still "Errors"?
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16:10
Episode 64: Aligning Yourself With the Company's Risk Profile
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16:01
Episode 63: Fulfilling Friday: SMS Spamming Saved
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18:46
Episode 62: The Peculiar Failure of Correctly Predicting Problems
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21:24
Episode 58: When You Can’t Iterate
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13:31
Episode 55: Writing Your Job Out Of Existence
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14:05
Episode 54: Shadow Your Colleagues
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27:59
Episode 51: How Company Culture Impacts Code Delivery
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26:44
Episode 49: Falsehoods Programmers Believe About Projects Part 2
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17:59
Episode 48: Falsehoods Programmers Believe About Projects
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20:32
Episode 47 - Maintenance Work as a Flight to Safety - A Manager's Perspective
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15:13
Episode 44 - Do More With Less
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11:12
Episode 42: Iteration as a Defense From Micromanagement
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44:59
Episode 37: Interview Insights - Changing the Game for Interviewers and Candidates
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19:59
Episode 35: The Subtle Art of Refusing Meetings
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13:34
Episode 33: How to be a Terrible Teammate
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39:40
Episode 27: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 2
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26:31
Episode 26: The Ticket Master - Computerizing India’s Railways with Aadil Farid, Part 1
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30:41
Episode 20 - Shrink Mode
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13:22
Episode 16 - Tricks to Facilitate Conversation
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40:52
Episode 12 - Company Culture Pt. 2 with Thomas Morris
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25:11
Episode 11 - You Can't Build to Spec
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51:17
Episode Six - How Company Culture Makes Or Breaks Your Team
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19:06
Episode Five - Perverse Incentives