In this fast-paced executive simulation, learners step into the role of the newly appointed Chief Operating Officer at Venn Commercial Logistics, an eight-year-old, $42M fleet maintenance enterprise headquartered in Chicago. Recruited by the board to professionalize operations across six Midwest hubs, the COO immediately faces the classic "Founder's Trap." Founder and CEO Kieran Brody remains deeply entrenched in frontline operations: 91% of routine expenditures over $5,000 flow to his desk, creating an 11-day approval bottleneck. Following an emergency tractor shortage at the Columbus depot, Kieran bypassed the company's $25,000 procurement threshold with an 11:15 PM text message greenlighting an unbudgeted $78,400 spot lease at a 14% pricing premium.
The incident triggers acute organizational fallout. Midwest Regional Director Amara Okonjo warns that middle managers are burning out under dual command chains, while Lead Independent Director Diane Castille cautions that institutional investors will freeze Series B growth funding until formal Levels of Authority (LOA) are certified. In the core roleplay interaction, the learner must confront Kieran in an executive negotiation. To succeed, learners must resist the temptation to rely on bureaucratic policy enforcement or board pressure, instead reframing structured delegation as an operational accelerator that unlocks frontline velocity and resolves Kieran's 65-ticket daily inbox backlog.
Facilitators can run this case in 10 to 15 minutes as an intensive warm-up or standalone micro-lab on scaling transitions. Debrief sessions should explore the tension between entrepreneurial agility and institutional governance, challenging participants to reflect on how leadership roles must evolve during high-growth inflection points.
Learning objectives
- How the transition from informal startup hustle to professionalized operations inevitably triggers Greiner's "Crisis of Autonomy."
- Why interventionist founders resist delegation out of fear of operational stagnation and perceived obsolescence, rather than malice.
- Techniques for framing governance and Levels of Authority (LOA) as operational accelerators rather than bureaucratic roadblocks.
- How to manage dual-reporting friction and prevent middle-management burnout when founders bypass formal operating hierarchies.
About the authors
LiveCase Studio develops dynamic simulation experiences for business schools and corporate leadership programs globally. Its interactive case studies place participants directly inside authentic organizational dilemmas to build judgment, stakeholder alignment, and strategic decision-making capabilities.
LiveCase Studio
LiveCase Studio designs interactive executive decision-making simulations that challenge leaders to navigate complex organizational friction, governance transitions, and high-stakes stakeholder negotiations in real time.
Who is this for?
Current and aspiring C-suite executives, operations directors, and general managers managing scaling transitions, founder-led growth friction, or corporate governance implementations.