Modern CTO

Alan Williamson, author and advisor who helps CTOs and VPs of engineering step up into senior technical leadership. He talks about communicating with non-technical executives, budgeting and quantifying engineering costs, managing technical debt intentionally, aligning engineering with business needs, and the necessity of articulating a clear technical vision.

Guy Kawasaki, legendary Apple evangelist and Chief Evangelist at Canva, explains why everyone needs privacy in the digital age. He covers why Signal matters, how metadata exposes more than you think, the risks of mainstream messaging, practical safeguards, and tips for persuading others to switch. Short, urgent, and focused on action.

Stephen Poletto, Field CTO at Span, helps instrument dev processes and advise on AI-driven engineering. He warns against hype-driven decisions and champions data-first approaches. Conversation covers harness engineering, measuring real vs perceived productivity, AI-driven workflow shifts, and practical guardrails for safely using agents and tooling.

Ashley Goodall, leadership expert and bestselling author who studies the human side of continuous change. He contrasts management’s love of change with employees’ experience of constant disruption. He explains when change helps versus when it harms, outlines five psychological harms of nonstop reorganizing, and argues for stability to enable creativity and meaning at work.

Tom Chi, Google X co-founder and clean-tech inventor, and author of Climate Capital. He discusses targeting the 30 industries causing most planetary harm and intercepting pollution at production. He explains factory-led construction, cobotics, and why profitable physical technologies scale. He outlines At One’s hands-on investing that prizes unit economics over performative green.

Don McMillan, former Bell Labs chip designer turned visual stand-up comic. He recounts leaving semiconductor engineering after burnout, inventing PowerPoint-driven comedy, and using engineering instincts to craft timing and visuals. Stories include a pivotal radio moment, adapting material for corporate tech crowds, and touring with AI-themed bits.

Rajeev Rajan, CTO at Atlassian and champion of developer joy, talks about why joyful engineers outperform productivity metrics. He explains why many great leaders are accidental managers and how career ladders should let top coders stay technical. Conversation covers scaling leadership as teams grow, staying connected across locations, and building trust, people, and developer-focused tools.

Rob Kalwarowsky, bestselling author and leadership coach who created the GOLD method, shares career-acceleration strategies. He explains why writing and declaring goals boosts success. He breaks down updating limiting beliefs, leveraging strategic relationships, practical networking moves, and why action and public repetition of goals create opportunities.

Anand Narasimhan, CTO of S-Docs and former Salesforce engineer, built native, secure document automation for regulated enterprises. He discusses why disconnected Word/PDF workflows create compliance and data-leak risks. They cover shadow IT and employees bypassing tools, the cost of documentation errors, and why automation must come before autonomous AI.

Tony Davis, agentic strategist who builds and governs agent workforces. Dr. Mark Burgess, theorist behind Promise Theory and CFEngine. They explore how promise-based coordination replaces command control. They discuss agent autonomy, peer rejection and swarm-inspired cooperation. They also examine biological metaphors like immune systems and bee behaviour for stable, scalable agent fleets.