The MCTO Awards: Who is THE Modern CTO of 2025? - Modern CTO Recap
Podcast: Modern CTO
Published: 2025-12-31
Duration: 31 minutes
Guests: Art Hugh, Rebecca Carr, Adrian McDermott, Miles Spencer, Jack Tam
Summary
In a special awards episode, the podcast crowns Rob Duffy from HealthEdge as the Modern CTO of 2025. The episode revisits the year's standout moments in tech leadership advice, ethical debates, and personal anecdotes.
What Happened
Art Hugh from Lenovo emphasized the importance of taking risks in AI implementation, urging CTOs to aim for 'speeding tickets' over 'parking tickets'. This metaphor highlights the value of bold action rather than cautious stagnation in technology leadership.
Rebecca Carr, CEO at Smart Recruiters, introduced a novel hiring strategy by asking candidates to recount negative feedback they've received and their responses to it. This approach serves as an effective test for self-awareness and adaptability, key traits for tech leaders.
Adrian McDermott from Zendesk suggested that leaders should be unpredictable in their management style, likening effective leadership to a slot machine rather than a vending machine. This analogy underscores the need for dynamic and flexible leadership strategies in the tech industry.
Miles Spencer from Reflecta sparked significant ethical discussions with his use of AI to communicate with his deceased father. This controversial topic raised questions about the implications and boundaries of technology in personal relationships.
Jack Tam from Intuit MailChimp advised against immediate responses to emotionally charged emails. He recommended drafting responses elsewhere and revisiting them after calming down, promoting mindful communication in professional settings.
The episode also featured a humorous personal anecdote from Joel about removing sugar from his diet, which unexpectedly increased his wife's attention. This light-hearted moment was a departure from the more serious discussions but added a relatable touch.
Phil T. from Zscaler used a story about the Winchester Mystery House to illustrate the importance of organized tech stacks. His storytelling highlighted the parallels between architectural chaos and technological inefficiencies.
Ultimately, Rob Duffy from HealthEdge was awarded the title of Modern CTO of 2025 for his impactful advice on AI adoption, which resonated widely and was frequently recommended by Joel.
Key Insights
- Lenovo's Art Hugh advocates for risk-taking in AI implementation, using the metaphor of 'speeding tickets' over 'parking tickets' to encourage bold action in technology leadership.
- Smart Recruiters' CEO Rebecca Carr employs a hiring strategy that involves candidates discussing negative feedback they've received, assessing self-awareness and adaptability.
- Zendesk's Adrian McDermott compares effective leadership to a slot machine, suggesting that unpredictability and flexibility are crucial in management styles.
- Reflecta's Miles Spencer sparked ethical debates by using AI to communicate with his deceased father, raising questions about the boundaries of technology in personal relationships.