Developing Systems Thinking in Newly Appointed VPs of Engineering
Designed for Recently promoted VPs of Engineering at scaling tech companies (100–500 employees) facing their first executive-level leadership roles to spark real collaboration and high-energy learning.
A 90-minute, high-impact in-person workshop conducted during a leadership offsite. These new VPs are navigating ambiguous, rapidly scaling environments, struggling to shift from tactical firefighting to proactive, strategic thinking. They feel overwhelmed by interconnected problems and the pressure to demonstrate executive-level impact quickly.
Chain Reaction Demo
Kick off with a physical domino chain reaction exercise. Each participant gets to place a domino, but must predict the effect of their piece on the entire chain. A deliberate 'gap' is introduced without warning. After the chain is triggered and breaks, participants debrief what happened and why.
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Why this works
Physical demonstrations spark curiosity and make abstract interdependencies tangible. The payoff is an immediate, memorable 'aha!' around the ripple effects in systems.
Linear Thinking Trap Reveal
Present a real engineering leadership scenario: 'The build pipeline is slow, so we’ll double the compute resources.' Poll the room: Who thinks this fixes the problem? Reveal data and a system map showing deeper causes like code review bottlenecks and unclear ownership.
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Why this works
Exposes common misconceptions and primes minds to question simple fixes. Using a realistic example surfaces unconscious biases toward linear problem-solving.
Safe Experiment—Sticky Note Mapping
In small groups, give each team a set of sticky notes and ask them to map out the key players, processes, and tools involved in shipping a feature. Each group draws arrows to show dependencies, no judgment—just exploratory.
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Why this works
Hands-on, low-pressure mapping encourages participation without fear of being ‘wrong’. It surfaces the hidden system without scrutiny.
Systemic Domino Challenge
High-energy relay: Teams compete to solve a simulated bottleneck in a fictional engineering org. Each table gets a ‘problem card’ (e.g., code review backlog) and must act out a change—while a facilitator quickly updates a live system map showing the ripples (e.g., QA is now overwhelmed). Fast rounds, competitive spirit.
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Why this works
Injects energy, fun, and memorable insight into how interventions cause unexpected side effects. Reinforces systemic complexity under time pressure.
CTO’s Dilemma: Fix the Root
Facilitator reads a real blinded case: ‘As CTO, you notice a string of missed deadlines and low morale after a major re-org. Do you (a) change project management tools, (b) run a training, (c) dig for systemic causes?’ Participants debate what makes the root cause elusive.
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Why this works
Grounds systems thinking in a dilemma with real stakes. Forces participants to confront the tension between quick fixes and systemic diagnosis.
System Map Self-Reflection
Each participant has 2 minutes to sketch a ‘heat map’ of their org—highlighting areas where they’ve recently intervened (green), fires they’re constantly fighting (red), and areas untouched (grey). They pair up to share one insight or surprise.
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Why this works
Active personal reflection cements learning, while peer sharing builds safety and connection. Visualizing their system makes abstract learning actionable.
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