Leadership at Scale:

Cultivating Capabilities and Stewarding Culture

Abstract

Facing rapid expansion, a global technology and retail giant partnered with Insight Experience to develop a three-day leadership program. The award-winning initiative addresses concerns about cultural dilution and sustaining business velocity through executive insights, a simulation experience, and peer learning. With thousands of Directors participating to date, it continues to strengthen leadership, decision-making, networking, and cultural stewardship at scale.

Challenge

As this multinational technology and e-commerce leader rapidly expanded, senior leaders identified two major concerns: the dilution of culture and the risk of slowing pace and productivity. Directors, a critical leadership tier, were being onboarded at a rapid pace, with more than 50% having less than two years of tenure. The organization needed an innovative, engaging, and highly relevant learning experience that would strengthen leadership skills at scale; reinforce a common language and shared priorities about culture; enable Directors to drive strategic execution across diverse geographies and functions; and provide a network for leaders to share challenges and insights.

Solution

Insight Experience collaborated with the company to create Cultural Stewardship at Scale, a three-day immersive learning experience that integrates executive insights, a custom business simulation, and structured peer learning. Senior leaders share their leadership lessons to reinforce cultural priorities, while the custom-designed simulation immerses Directors in realistic decision-making scenarios that mirror real-world challenges. Throughout the program, participants engage in peer learning circles that allow them to discuss leadership challenges specific to their roles, which foster deeper connections and shared problem-solving. Additionally, structured role-play interactions and executive coaching sessions provide real-time feedback, enhancing participants' self-awareness and leadership effectiveness. The program is designed to be adaptable for both virtual and in-person delivery, which ensures broad accessibility for a global audience.

Learning Objectives

Cultural Stewardship at Scale creates actionable insight into how leaders operate within the organization, equipping them with practical strategies to navigate complex challenges. Participants develop key leadership capabilities, including:

• Strengthening decision-making skills in high-velocity, high-impact environments

• Enhancing cultural stewardship and reinforcing organizational values

• Leading and developing high-performing teams

• Managing trade-offs and strategic priorities at scale

• Building cross-functional and cross-regional leadership networks

Design Highlights

Cultural Stewardship at Scale distinguishes itself through multiple innovative design elements, particularly its custom-designed simulation. Set several years in the future within a fictional but realistic business unit, the simulation creates an even playing field, ensuring that no one group has an inherent advantage in understanding the case study. This forward-looking approach allows participants to engage in decision-making scenarios that feel relevant and align with real-world leadership challenges.

A key pillar of the program is cultural stewardship, so the simulation is carefully designed within the context of the organization. By immersing leaders in a familiar cultural framework, without the distractions of an existing business unit’s specific details, the simulation enables them to focus on leadership decisions and their broader impact.

Another integral part of the program is the live role plays, where participants engage in simulated leadership interactions and receive immediate feedback. The simulation includes three role plays, each designed to help participants apply leadership principles in real-time scenarios and reinforce cultural stewardship. Executive coaches observe and debrief each session, while structured comparative learning discussions further analyze decisions made during the simulation, highlighting their impact on business outcomes.

Scalability is another critical aspect of the program. Designed to support up to 144 Directors per session, the program maintains a high level of interaction while allowing broad reach across the organization.

Finally, pre- and post-session coaching ensures that participants receive guidance before and after the program. This reinforces learning retention and application in their daily leadership responsibilities.

Program Agenda

Day 1: Mental Models

• Executive speaker session: Leadership Lessons from Experience and Mental Models for Protecting our Unique Culture

• Introduction to the business simulation and team formation

• Peer learning circles: Identifying and addressing leadership challenges

Day 2: Scaling Yourself as a Leader

• Executive Speaker Session: Strategies for Scaling your Leadership Impact

• Simulation Round 1: Business decisions and leadership trade-offs

• Role play: Providing feedback on stewarding culture while leading and guiding direct reports to shift their mental models for scaling leadership

• Learning discussion: Comparative decision analysis and peer insights

• Peer Learning Circles: Crowdsourcing solutions for real-world leadership challenges

• Executive Speaker: How to Drive High Performance at Scale

• Simulation Round 2: Long-term strategic decision-making

• Role plays: Helping a leader understand their role in stewarding culture, guiding direct reports to recognize their influence, and supporting them in scaling and growing. Additionally, participants engage in peer conversations to build relationships, frame conflicts productively, and identify leadership signals for their peers.

• Action planning: Identifying commitments and next steps

The program design intentionally mixes large-group activities with small-group discussions and is highly interactive:

Simulation Overview

The business simulation is the cornerstone of the program, providing an immersive experience where participants make leadership decisions under pressure while balancing short- and long-term business growth. It challenges them to manage complex stakeholder relationships and practice cultural leadership through realistic, scenario-based challenges.

Participants work in teams, each assuming the role of a leader tasked with scaling a global business while innovating. They navigate trade-offs between speed and quality, innovation and stability, and cultural integrity and short-term results. The simulation provides a hands-on opportunity to witness the consequences of leadership choices, reinforcing key behaviors in a dynamic environment.

By offering qualitative insights into how critical leadership behaviors like coaching, teaching, and communicating impact business results and financials, the simulation helps participants refine their strategic thinking and leadership effectiveness. It fosters learning through practice, equipping Directors with the confidence and skills to address real-world challenges. Scenarios interconnect, requiring participants to weigh trade-offs, consider business and cultural impacts, and recognize how leadership behaviors influence organizational outcomes.

History and Results 

Since its launch in 2019, Cultural Stewardship at Scale has evolved based on participant feedback and organizational needs. It has been delivered globally, with sessions held in North America, Europe, Asia, and virtually, reflecting the organization's extensive operational footprint. Engagement from senior leadership and tailored content ensures the program's relevance across diverse geographic and operational contexts.

Participants report substantial benefits from the program, including a better understanding of organizational dynamics, the enhanced ability to implement strategic changes, and improved networking opportunities. Participants highlight actionable insights about leading their teams and stewarding the culture.

One participant noted that it was “a really well developed simulation, and felt quite rooted in reality, especially the different personalities, and the external forces.” Another Director noted: “The content was highly conceivable and not too abstract. Struck the right balance in terms of the team being able to draw on [the company] perspective/experience but also having to play outside our expertise.” Positive feedback emphasizes the program's role in fostering a robust leadership community equipped to tackle future challenges.

The program continues to reach a global audience, reinforcing leadership at scale. It has earned industry recognition, including a Gold award from the Brandon Hall Group for Best Unique or Innovative Learning and Development Program as well as a Silver award for Best Use of Games and Simulations for Learning. Participant satisfaction remains high, with an average effectiveness rating of 4.65/5.0. Directors who have attended report increased leadership confidence, enhanced decision-making skills, and a stronger ability to drive strategic execution.

Beyond individual benefits, the program has strengthened leadership pipelines, improved cross-functional collaboration, and enhanced cultural stewardship. The combination of experiential learning, executive insights, and peer networking has contributed to lasting leadership development, ensuring that Directors are equipped to navigate complexity and drive business impact effectively.