The Debugged Agenda

Can AI make you a better leader and a better communicator? Senior Director of Engineering Max Schubert uses ChatGPT every day as an emotional intelligence coach. He uses it to rehearse high-stakes conversations, prepare for difficult one-on-ones, and get critique on his own work.

In this episode of The Debugged Agenda, host Jason Short (CTO and Co-Founder of CH2 Solutions) talks with Max about using AI for leadership, psychology, and communication. They also cover why AI should make people more capable instead of replacing them, and how to choose between full-time engineers and contractors.

You’ll learn:
 → How to use ChatGPT voice mode to practice difficult conversations
 → Why Max adds “critique me” to his base AI instructions
 → The risk of AI becoming a crutch for engineering teams
 → How specific feedback raises the EQ of a whole room, including the boardroom
 → When staff augmentation beats one-off contractors in complex codebases
 → Why nearshore engineering teams in overlapping time zones build more trust

🎙️ ABOUT THE DEBUGGED AGENDA
 The Debugged Agenda explores the technology decisions that shape organizations, from leadership and talent to innovation, growth, and acquisition. Host Jason Short sits down with CEOs, CTOs, founders, and investors.

🔗 Learn more about CH2 Solutions: https://ch2solutions.com

👍 Like, subscribe, and share this episode with a leader who’s figuring out AI for their team.

In this episode of The Debugged Agenda, host Jason Short sits down with Bobby Tahir, a four-time CTO and two-time founder with more than two decades of experience leading technology organizations across startups, private equity-backed companies, and large enterprises. Bobby has been in boardrooms for nearly 20 years and has developed a clear-eyed view of what separates CTOs who thrive at the executive level from those who struggle and eventually wash out.

The conversation opens with a reframe most tech leaders need to hear: the board is not your adversary. They want you to succeed. But wanting you to succeed and making it easy for you are two different things. Bobby walks through why the CTO role carries a translation burden no other C-suite executive faces, why traditional tech metrics fall flat in board settings, and how to develop what he calls “competency triggers” that help boards connect technical work to business outcomes they actually care about.

In this episode of The Debugged Agenda, the conversation opens with a live example: Keating recently used Claude as a full partner to design an enterprise service experience from the ground up, and walks through why service design, not AI tooling, is now the true competitive moat. From there, she and Jason examine the widening gap between what AI makes possible and what most executive teams are equipped to manage, including a pointed observation that most C-suites still have no shared operating system, no clear decision-making discipline, and no common language for talking about what technology actually delivers.

Part 2 with John Basso who specializes in corporate transformations is now LIVE. 

Our conversation about organizational trust reaches beyond technology and dives into the psychology of team performance.

In this first episode of Debugged Agenda, Jason Short sits down with John Basso for an unfiltered conversation about what actually breaks engineering organizations. Not the version that gets shared at conferences. The real one.

They get into the moments where leadership loses trust in the tech team, where communication breaks down before anyone admits it, and where the decisions that seem reasonable in the moment become the ones you are still cleaning up two years later.

If you lead engineers, work alongside engineers, or hire them — this one is for you.