The Challenge

A software design company was undergoing major organizational shifts, including the adoption of a new customer transaction model and the integration of AI across its products. The senior executive team, led by the CTO, recognized that these changes were putting significant strain on how leaders worked together.

Despite their individual strengths, the executive team was struggling with fractured dynamics that were slowing execution and stifling honest dialogue. Specifically, the team was facing:

• Low trust scores and fractured team dynamics across the leadership group.
•  Conflicting views on product management strategy, with no shared framework for resolution.
•  Silence around key concerns due to fear of conflict or seeming incompetent in front of peers.
• Missed deadlines and misalignment across functions, eroding confidence and momentum.
  
  

The CTO knew that without a foundation of trust and open communication at the executive level, the broader organizational transformation would not succeed.

Pre-Work: One-on-One Leader Interviews

Before the team convened, SIY Global conducted in-depth interviews with each senior leader. These confidential conversations surfaced the unspoken tensions, competing priorities, and individual concerns that were affecting the group's ability to work together.

Focused Sessions

The in-person sessions were designed to move the team from guarded politeness to real dialogue. Key modules included:

• Empathy Building — Understanding peer motivations and the pressures each leader faced in their role.
• Voicing the Unspoken — Creating a safe space to address fears, concerns, and the topics the team had been avoiding.
• Team Alignment & Trust — Establishing shared goals and a common language for how the team would operate through the transformation.
• Commitments to Change — Each leader made personal accountability commitments to sustain the progress beyond the session.