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Tiffany Christner, Chief of Staff for Cloud Platform and Engineering at Boeing, joins the OKR Podcast to discuss Boeing’s transformation journey, the adoption of OKRs, and the role the WorkBoardAI platform and WorkBoard services play in strengthening alignment, transparency, and cultural change across a complex global engineering organization.
The Challenge
- Lack of a Safe, Shared Space for Strategic Conversations:
Before WorkBoard, Tiffany’s teams lacked a collaborative environment where aspirational goals could be openly discussed. Many of the most essential strategic and cross-functional conversations “had not yet happened” simply because there was no structured or psychologically safe place for them.
- Difficulty Aligning on Outcomes Across Functions and Systems:
Her organization, operating heavily in software development, struggled to reconcile existing Agile tools and PI planning with the need to align around broader business outcomes. This created uncertainty about dependencies across finance, HR, product, and engineering, making alignment more difficult.
- Cultural Resistance to Transparency and Working in the Open:
The shift toward visible goals and progress created discomfort in a culture where professional excellence and perfection are paramount. Teams were hesitant to expose incomplete work, voice uncertainty, or ask for help, despite the increasing need for cross-team collaboration.
- Complexity of Driving Change Amid Organizational Transformation:
Boeing Digital was undergoing modernization for an AI-driven future, and without a consistent mechanism for communication and alignment, teams moved at different paces. The organization lacked the “muscle memory” to adopt new behaviors together, complicating the transformation.
The WorkBoardAI Solution
- Created a Cultural Springboard for Collaboration, Trust, and Ambition:
WorkBoard provided the safe collaborative space that unlocked new conversations, healthy debate, and a greater willingness to ask for help. This shifted the mindset from fear of failure to permission to succeed and encouraged aiming higher across teams and roles.
- Enabled Outcome-Driven Thinking Over Activity Orientation:
By guiding teams toward defining measurable results instead of managing task lists or Kanban boards, WorkBoard helped engineering, architecture, and functional groups focus on the impact of their work. The shift produced clearer strategic intent and more meaningful alignment.
- Accelerated Strategy Execution Through AI-Assisted Drafting and Insight:
WorkBoardAI advanced thinking faster by offering structured drafts of objectives and key results, sparking deeper discussion and creativity. Tiffany described the experience as “magical,” emphasizing how AI became a genuine force multiplier for strategic clarity.
- Established a Scalable Operating Rhythm that Strengthens Alignment and Decisions:
Through Power Tuesday reviews, shared scorecards, confidence narratives, hot-topic tracking, and Canvas-based quarterly planning, WorkBoard enabled a predictable operating rhythm. This structure improved cross-functional collaboration, sped up issue resolution, and supported better decision-making across a global, largely remote organization.
Conclusion
With WorkBoardAI, Boeing’s Cloud Platform & Engineering organization strengthened its culture of transparency, cross-functional alignment, and outcome-driven execution. AI-assisted OKR creation, shared scorecards, and a consistent weekly operating rhythm accelerated strategic conversations, clarified priorities, and helped the organization shift from activity-focused work to meaningful, measurable business results.
