PyData London 2025

Debugging Leadership: Six Errors when Moving From Code to Management
06-08, 14:45–15:30 (Europe/London), Hardwick Hub

Transitioning from a hands-on Pythonista to a leadership role is a journey filled with challenges, and like debugging code, it requires identifying, isolating, and fixing problems. In this talk, I’ll share eight key lessons from my journey from Data Scientist to Co-Founder of a small software company, framed as Python errors.

From battling imposter syndrome (ValueError: self-worth not defined), to learning to delegate (DeadlockError: unable to release control), and avoiding burnout (RuntimeError: system overload), this talk offers actionable advice for anyone navigating the leap from technical contributor to technical leader.

Expect a mix of humour, relatable stories, and hard-won lessons as we explore how debugging leadership challenges is just as rewarding (and occasionally frustrating) as debugging code. Whether you’re considering a leadership role or already on the journey, this session will leave you with practical insights to navigate common pitfalls and approach a leadership transition with a clearer understanding of what to expect.


Transitioning from a technical role to leadership is a unique challenge; it’s no longer about writing clean code or optimizing performance but about empowering teams, making decisions, and balancing competing priorities. In this talk, I’ll share eight key lessons from my own experience. I frame these lessons as Python errors that technical professionals will find relatable and actionable.

Key Lessons:

ValueError: self-worth not defined: Imposter syndrome can hit hard when stepping into leadership. I’ll share how I redefined my sense of value and impact beyond just writing code.

DeadlockError: unable to release control: Delegation doesn’t come naturally to many of us. I’ll discuss how learning to let go and trust your team is critical for scaling your impact.

KeyError: culture not found: Leadership isn’t just about building great products; it’s about building great teams. We’ll explore how to create a culture where people can thrive.

AttributeError: clear_message not found: Communication is the cornerstone of effective leadership. I’ll share how I developed this skill to articulate vision, handle negotiations, and navigate tough conversations.

TypeError: instant_gratification is not callable: Unlike coding, leadership rarely provides quick wins. I’ll explain how to find satisfaction in long-term progress and team success.

UnhandledImpactError: cascading effects detected: How you show up as a leader has a ripple effect on your team and clients. I’ll discuss how to be intentional about your presence and its impact.

DependencyError: support module not imported: You can’t do it alone. I’ll share the value of building a support network of mentors, peers, and advisors.

RuntimeError: system overload: Burnout is real, and leadership can amplify it if you’re not careful. We’ll explore strategies to prioritize your own well-being as a leader.

What You’ll Gain:

This session is designed to help technical professionals better understand the realities of leadership transitions. By framing common challenges as Python errors, it provides a relatable and engaging way to explore the pitfalls and opportunities of stepping into leadership. Attendees will leave with:
Knowledge of what they’re getting themselves into and the challenges they might face.
Lessons learned from my personal experiences of transitioning to leadership.
Tools and advice to approach leadership transitions with practical strategies and a grounded perspective.

Whether you’re contemplating a leadership role or already on the journey, this talk will provide valuable lessons to help you lead with purpose and avoid common mistakes along the way.


Prior Knowledge Expected

No previous knowledge expected

Dr. Matthew Upson is Co-Founder of Mantis NLP, an AI consultancy specializing in delivering impact through natural language processing and generative AI. With over a decade of experience in data science and software development, he has worked across academia, government, and industry to build innovative AI solutions.

At the UK Government Digital Service (GDS), Matt contributed to some of the first applications of AI for GOV.UK, and developed an approach to automating workflows "Reproducible Analytical Pipelines" which is now widely used across government. Matt is a founding member of the Data Science Section of the Royal Statistical Society, and a fellow of the Software Sustainability Institute.

Matt lives in Valencia, Spain and is a dedicated (very) amateur triathlete and former bushcraft instructor who enjoys connecting with nature. His talks combine technical expertise with personal stories, in a humorous and informal way.