In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub are joined by Kevin Goldsmith, a seasoned tech leader with a background in both music and technology. Kevin shares insights from his early career in the music industry, his journey through various tech roles, and his book 'It Depends'. The discussion covers important topics like learning from failure, managing tech debt, and the impact of AI-assisted coding. Kevin also talks about the value of retrospectives, even after successful projects, and shares experiences from his tenure at Spotify. As a fun bonus Brad and Kevin both discuss their histories as record label owners and conclude by recommending some of their new favorite music.

• 00:00 Introduction and Guest Welcome
• 00:55 Record Label Stories
• 02:42 Kevin's Career Journey
• 07:34 Writing 'It Depends'
• 13:19 Lessons from Failure
• 18:04 Spotify Retrospectives
• 25:02 Feature Requests and Fun Stories
• 27:42 Exploring Music Algorithms
• 28:36 Technical Challenges and Business Implications
• 29:23 The Social Aspect of Music Sharing
• 31:29 Managing Multiple Spotify Accounts
• 33:00 Tackling Tech Debt in Monolithic Systems
• 42:23 AI Assisted Coding: A Tool for the Future
• 48:40 Music Recommendations and Closing Remarks

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/
• Kevin Goldsmith: https://www.linkedin.com/in/goldsmith/
• It Depends Book: https://itdependsbook.net/
• Tacocat: http://tacocatdotcom.com/
• The Telescreens: https://linktr.ee/Telescreens

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #retrospectivs #ai #aiassistedcoding #punkrock

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a recent incident in a small engineering team that highlights challenges of managing technical debt even with skilled developers and robust code review processes. They explore the importance of refactoring in agile methodologies, the pitfalls of large pull requests, and the complexities of quantifying and prioritizing technical debt. The conversation touches on the limitations of traditional code review processes and the potential of automated CI tools to enforce code quality. The episode underscores how even well-intentioned teams can fall prey to subtle coding anti-patterns and offers insights for improving tech debt management at different organizational scales.

• 00:00 Introduction and Welcome
• 00:30 Discussing a Recent Incident
• 00:58 Importance of Code Reviews
• 03:00 Challenges in Code Refactoring
• 05:25 Code Review Process and Human Error
• 07:22 Tools and Strategies for Code Quality
• 08:11 Evaluating and Managing Tech Debt
• 15:47 Conclusion and Call to Action
• 16:06 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/
• Defining, Measuring, and Managing Technical Debt - Google Research https://ieeexplore.ieee.org/document/10109339

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #codereviews #cicd

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss a recent OpenAI study on AI's effectiveness in completing real-world freelance software engineering tasks. They delve into the results showing that AI models completed only 26% of tasks successfully, highlighting current limitations. The conversation transitions to broader topics including the increasing use of AI in various industries, the potential displacement of jobs, and the essential skill of learning to work with AI. They also explore the energy consumption concerns related to AI queries and the possible environmental impact. The discussion reflects on the evolving nature of work and technological revolutions, and speculates on the future role of AI in everyday tasks.

• 00:00 Introduction: The Next Revolution
• 00:20 AI Coding Experiment on Upwork
• 02:35 Results and Analysis of AI Performance
• 03:30 Challenges and Limitations of AI
• 06:09 AI in the Workplace: A New Mandate
• 08:12 The Rise of Vibe Coding
• 11:00 AI Natives vs. AI Immigrants
• 12:41 The Hype Machine and Future of AI
• 15:22 Energy Consumption and Environmental Impact
• 19:50 Conclusion: The AI Revolution Continues

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/
• OpenAI Research Paper: https://openai.com/index/swe-lancer/

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #ai #aicoding #vibecoding #aiassistedcoding

 

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome special guest Ted Neward, a senior distinguished engineer at Capital One, joins the hosts to discuss the challenges and intricacies of engineering leadership and technology culture. Ted shares his diverse experiences, from his previous roles at Rocket Mortgage and Smartsheet to his current position. The discussion delves into the often overlooked aspects of job descriptions, interview processes, and the importance of measurable and actionable performance expectations. Ted also reflects on the use of coding projects in interviews, the role of AI tools in programming, and the necessity of training interviewers to avoid unconscious bias. This episode provides valuable insights into creating effective and inclusive engineering cultures.

• 00:00 Introduction and Guest Welcome
• 00:34 Ted's Professional Journey
• 01:27 Exploring Esoteric Programming Languages
• 03:11 Tech Culture at Rocket Mortgage
• 04:16 Challenges in Job Descriptions and Interviewing
• 08:02 The Importance of Leveling Guidelines
• 11:36 Defining Good Code
• 19:02 Interview Process and Structural Guidance
• 25:53 Interview Training and Culture Challenges
• 27:09 Unintended Consequences of Filtering
• 27:59 Systems Thinking in Hiring
• 30:21 Bias and the Interview Process
• 31:28 Sample Coding Projects in Interviews
• 35:44 AI in the Hiring Process
• 43:29 The Philosophy of Interviewing
• 47:50 Concluding Thoughts and Reflections
• 49:50 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/
• Ted Neward: https://www.linkedin.com/in/tedneward/

#podcast #technology #leadership #ctos #technicaldebt #management #leadership #problemsolvingtechniques #problemsolvingstrategies #engineering #entrepreneurship #engineeringmanagement #hiring #engineeringtalent

 

 

 

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the importance of having an implementation plan in software development. They emphasize the role that written plans play in fostering collaboration and scaling projects. Through a candid conversation originally recorded in the summer of 2024, they dive into the nuances of translating business requirements into code, the core competencies required for engineering leaders, and best practices for creating effective implementation plans.

The episode also addresses common challenges engineers face, such as decision paralysis and the reluctance to share early ideas, while offering strategies for overcoming these hurdles. The hosts also share a comprehensive checklist for determining when a written implementation plan is necessary, touching on topics like schema changes, new technologies, and coordination across teams. The importance of a supportive, feedback-rich culture in engineering teams is highlighted as a key factor in successful project execution.

• 00:00 Introduction to the Podcast
• 00:48 The Core Skill in Software Development
• 02:29 Coaching Engineers on Implementation Plans
• 04:06 The Importance of Written Implementation Plans
• 06:02 Challenges and Solutions in Implementation Planning
• 09:57 Creating a Collaborative Culture
• 18:11 Guidelines for Formal Implementation Plans
• 23:09 Conclusion and Call to Action
• 23:34 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/

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub dive into the fascinating world of learning styles and their impact on teamwork in both remote and in-person environments. The conversation begins with Scott's personal trip, transitioning into an insightful discussion about the importance of understanding and leveraging different cognitive styles within engineering teams. The episode highlights how visual, kinesthetic, and auditory learning play crucial roles in effective communication and decision-making, supported by examples from strategic planning and mentoring junior engineers. The hosts stress the significance of intentional approaches to creating shared understandings, particularly in remote settings.

• 00:00 Introduction and Podcast Origins
• 00:50 Family Trip to Philadelphia
• 03:38 Work Trip to San Francisco
• 04:27 The Importance of In-Person Meetings
• 07:52 Learning Styles and Cognitive Styles
• 17:08 Mentoring in a Remote World
• 23:35 Conclusion and Final Thoughts
• 27:55 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/

 

In this bonus episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss their hands-on experience with an AI agent for updating their podcast website. They share the AI's initial success, followed by its struggle with a more complex task, leading to valuable insights. Key takeaways include the importance of knowing when to reset the AI, providing clear instructions, and the need for strong QA practices. They also touch on personal approaches to problem-solving and the balance between AI assistance and human oversight.

Watch the full video of their coding experiment on our YouTube Channel.

• 00:00 Introduction and Welcome
• 00:27 AI Coding Experiment
• 00:58 Challenges with AI Assistance
• 04:21 Human vs AI Problem Solving
• 05:40 Trust and Familiarity with Code
• 10:20 QA and Error Handling
• 12:04 Conclusion and Sign-off

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub welcome special guest Michael Natkin, a distinguished CTO with an Oscar and a James Beard Award. The discussion centers on the transformative impact of AI in coding and engineering, from the use of tools like Cursor and Code Rabbit to the potential of AI agents in automating complex tasks. The conversation delves into how AI is reshaping both junior and senior engineering roles, the nuances of prompting AI, and the promising yet cautious foray of non-technical users into the coding world. The trio also explores the future of software development and the importance of evolving with AI to safeguard career prospects in the tech industry.

• 00:00 Introduction and Welcome
• 00:36 Meet Michael Natkin: A Unique CTO
• 01:21 Michael's Journey: From Louisville to Glowforge
• 02:28 Achievements: James Beard Award and Oscar
• 03:31 Diving into AI and Coding
• 05:02 Real-World AI Experiences
• 05:19 AI Tools for Engineers
• 07:49 Challenges and Opportunities with AI
• 16:08 The Future of Junior Engineers
• 21:23 Exploring AI Tools and Systems
• 22:50 The Rapid Evolution of AI Tools
• 23:02 Non-Technical Engineers Making an Impact
• 23:37 Internal Tools and Their Effectiveness
• 24:41 Challenges with LLM-Generated Code
• 26:24 The Role of CTOs in Bridging Technical Gaps
• 27:11 Non-Technical Teams Using AI for Coding
• 30:02 The Future of AI in Software Development
• 30:14 Real-World Examples of AI Coding Success
• 31:33 Skepticism and Open-Mindedness in AI Adoption
• 33:19 The Evolution of Software Engineering
• 40:13 Encouraging Teams to Embrace AI
• 42:26 Final Thoughts and Reflections

In this episode of "How Many CTOs Does It Take?" podcast, hosts Scott Porad and Brad Hefta-Gaub discuss the critical role of a Chief Technology Officer (CTO) as a bridge between technology and business success. They delve into important topics such as organizing engineering teams, managing tech debt, and the trade-offs between enhancing engineering velocity and reducing operational costs. They emphasize the importance of clear metrics and accountability to measure team performance and align engineering efforts with business goals. Citing real-world examples and experiences, they provide insights into maintaining a balance between profitability and technical excellence. This episode also explores cultural shifts needed within organizations to prioritize collective objectives and improve overall efficiency.  

• 00:00 Introduction to the Role of a CTO
• 00:34 Meet the Hosts: Scott and Brad
• 00:47 Challenges Faced by Engineering Leaders
• 02:26 Organizing Engineering Teams
• 05:35 The Importance of Platform Teams
• 16:14 Balancing Profitability and Maintenance
• 20:50 Cultural and Process Considerations
• 25:33 Real-World Examples and Strategies
• 27:18 Contemplating a Shift in Platform Strategy
• 27:31 Defining Platform KPIs and Value
• 28:40 Customer Satisfaction and Platform Velocity
• 30:14 Balancing Cost and Velocity in Platform Teams
• 34:58 Organizational Structure and Conway's Law
• 39:19 Engineering Metrics and Success
• 42:36 Connecting Technology to Business Success
• 45:48 Implementing and Socializing New Ideas
• 52:37 Podcast Conclusion and Call to Action

In this episode of How Many CTOs Does It Take?, hosts Brad Hefta-Gaub and Scott Porad discuss best practices for running effective staff meetings. They explore different meeting structures, including ad hoc agendas, the 'ball of mud' pattern, and structured rhythms for sprint reviews and operations reviews. The duo emphasizes the importance of having a clear agenda to avoid unproductive meetings and suggest using categorized agenda items to align discussions with organizational goals. They also address the challenge of keeping attendees engaged and focused on key objectives. Practical tips for promoting fiscal responsibility, system uptime, and team engagement are shared to help leaders run more efficient and meaningful staff meetings.

00:00 The Importance of Meeting Agendas 00:21 Introduction to the Podcast 00:32 Different Approaches to Staff Meetings 01:14 Effective Meeting Structures 02:43 Tailoring Meetings to Company Needs 04:20 Balancing Structure and Flexibility 06:37 Addressing Common Meeting Issues 09:46 Implementing Structured Agendas 12:06 Engaging Attendees in Meetings 14:02 Conclusion and Podcast Outro