The CTO Playbook 79: What Engineers Really Need from Their Leaders: A Conversation with Massimo Belloni
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Jan 20, 2026 Massimo Belloni, Head of Machine Learning and Data Science at Docplanner and author of The Imposter newsletter, shares key insights on effective leadership. He emphasizes that true leadership is about people, not just technical skills, and how curiosity fosters trust. Massimo discusses the importance of autonomy in engineering, the unseen work that supports leadership, and learning from past mistakes. He encourages leaders to visualize future goals and act with intention, prioritizing transparency and the assumption of good intentions for team dynamics.
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People Over Tech
- Leadership in engineering is primarily about people, not technical mastery.
- Massimo says 95% of leadership problems are non-technical and the technical ones are easiest to solve.
Enable Autonomy, Not Answers
- Do give engineers autonomy, mastery, and space to grow rather than being the all-knowing oracle.
- Adam and Massimo emphasize enabling engineers with trust and room to own problems.
Invisible Work Compounds
- Invisible leadership work compounds and becomes visible only in hindsight.
- Massimo tracks progress by asking if things are better than when he took over.