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Tech Leadership Tuesday: Systems Thinking Essentials with Diana Montalion and Lena Reinhard

Published by O'Reilly Media, Inc.

Intermediate content levelIntermediate

Why every tech leader needs systems thinking (and what it actually means)

Ever found yourself nodding along when people mention “systems thinking” in meetings, articles, or conferences—not entirely sure what it means but sensing it might be important? You’re not alone.

In this Tech Leadership Tuesday, Lena Reinhard is joined by Diana Montalion, author of the popular book Learning Systems Thinking, for an accessible discussion to help you see how systems thinking is critical for addressing the real leadership challenges you face every day. Through relatable examples, you’ll grasp what terms like “linear thinking,” “emergent properties,” and “feedback loops” actually mean for your day-to-day decision-making and why understanding them is not optional for effective and impactful technology leadership. You’ll immediately improve your influence using systems thinking to break down communication silos, prevent architectural dead ends, and identify early warning signs of decisions that create future headaches.

Appropriate for aspiring and current tech leaders at all levels, this event will help you see your organization’s challenges more clearly and address them more effectively. Join us to discover why more and more tech leaders view their work through a systems lens—and how you can too.

Tech Leadership Tuesday is a dynamic monthly live event that helps empower people and technology leaders to become more effective and successful in their leadership roles. Each episode delves into a relevant topic for engineering leaders and, through a conversation between a host and guest, you’ll learn about common challenges, best practices, and lessons learned from the guest’s experience. During the event, you may ask the host and guest questions about the topic, their career journeys, or leadership in general.

What you’ll learn and how you can apply it

  • What abstract concepts like “emergent properties” and “feedback loops” actually mean and how you can apply them to your daily leadership challenges
  • How to identify decisions that are likely to create future technical and organizational headaches

This live event is for you because...

  • You want to move beyond a surface-level understanding of systems thinking and truly understand how it can improve decision-making.
  • You’re facing complex organizational challenges, feel stuck, and are open to a different way of thinking.
  • You’re looking to improve your influence and effectiveness as a current or aspiring tech leader at any level, and you want to broaden your mental toolkit.

Prerequisites

  • Come with your questions for Diana Montalion and Lena Reinhard
  • Have a pen and paper handy to capture notes, insights, and inspiration

Recommended follow-up:

Schedule

The time frames are only estimates and may vary according to how the class is progressing.

Tuesday, July 15, 2025, at 9:00am PT / 12:00pm ET

  • Interactive discussion and Q&A (60 minutes)

Your Hosts and Guests

Lena Reinhard

Lena Reinhard is a VP of engineering, leadership coach, and mentor who also hosts the podcast Leadership Confidential, featuring honest conversations about the joys and challenges of leadership. Having served the majority of her 20-year career in leadership roles with CircleCI, Travis CI, and as a startup cofounder and CEO, Lena is dedicated to helping leaders and their organizations succeed and thrive. She has partnered with a variety of remote, hybrid, and colocated companies at all stages, from startups to scale-ups, corporations, and NGOs.

Diana Montalion

Diana Montalion is a systems architect working at the intersection of software engineering, systems design, and human intelligence. She helps technical teams design scalable, adaptive systems by encouraging effective decision-making in distributed environments. For over 20 years, Diana has led complex initiatives for organizations including The Economist, The Wikimedia Foundation, Memorial Sloan Kettering, and Teach For All. Her talks and workshops combine practical tools with deeply human insights, helping technical teams think in systems, lead with insight, collaborate effectively, and deliver more-impactful outcomes.

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Skill covered

Organizational Leadership