In this episode of The Dark Arts of Team Optimization, hosts Kyle Johnson and Franz Aliquo interviews Todd Cantalupo, Senior Engineering Manager at KarmaCheck and Director Software Engineering at Meltwater where they talk about what makes engineering leaders truly effective not just in shipping code, but in evolving team dynamics. The conversation centers around agile transformations, why so many fail, and how building trust and psychological safety are essential for long-term success. This episode is for leaders who want to break the mold and actually connect with their teams at a human level.

Todd Cantalupo is an experienced engineering leader with over 25 years in the industry, having worked at organizations like Meltwater and Thunderhead. Known for his people-first approach, Todd has developed a leadership philosophy centered around trust, vulnerability, and psychological safety. He now consults under the brand "Lupo Empowerment," helping teams shift from fear-based to focus-driven work environments.

Expect to Learn:

- How Todd uses emotional intelligence and self-awareness as foundational tools for leadership.

- Why many agile transformations fail and how to prevent that.

- A framework for identifying and transforming fear within engineering teams.

- The power of empathetic listening and how it changes team dynamics.

- Why 50/50 role splits (like coding and scrum mastering) often don't work and what to do instead.

Episode Breakdown with Timestamps:

[00:00:00] - Teaser

[00:01:19] - Introduction of Todd Cantalupo

[00:02:18] - Turning the Mirror Inward: The Role of Self-Awareness

[00:04:58] - The Coaching Breakthrough That Changed Everything

[00:10:59] - Fear to Focus: How to Transform Team Mindsets

[00:28:46] - Why 50/50 Role Splits Don't Work

[00:31:15] - Unpacking Beliefs Through One Simple Exercise

[00:36:36] - The One Takeaway: Empathetic Listening

[00:38:25] - Where to Find Todd & Closing Remarks

📱 Follow our Guest :

👉 LinkedIn: https://www.linkedin.com/in/todd-cantalupo

👉 X: https://x.com/tcantalupo?lang=en

👉 Instagram: https://www.instagram.com/toddcantalupo/

👉 Company LinkedIn: https://www.linkedin.com/company/karmacheck

👉 Company Website: https://www.karmacheck.com/

📱 Follow the Hosts Kyle Johnson and Franz Aliquo:

👉 Kyle’s LinkedIn: https://www.linkedin.com/in/kyleclaytonjohnson/

👉 Franz’s LinkedIn: https://www.linkedin.com/in/franz-aliquo/

📱 Follow Holonic:

👉 Website: