Project Overview

As a design leader at Realtor.com, I co-led a strategic initiative to transform the company's quarterly planning process alongside a product design partner. Working with cross-functional teams across design, product management, engineering, and QA, we applied design research methodologies and a design thinking framework to understand organizational planning challenges and create a scalable solution. The resulting playbook, inspired by Ryan Singer's Shape Up methodology, fundamentally improved how teams planned, prioritized, and executed work across the organization.

Challenge & Organizational Context

Realtor.com's rapid growth had created a fragmented planning landscape that was hindering effective execution:

• Process Fragmentation: Teams operated with bespoke planning approaches, making cross-team collaboration and dependency management nearly impossible
• Chronic Churn: Frequent priority shifts and timeline changes created a cycle of re-planning that consumed significant time and energy
• Redundant Effort: Teams repeatedly performed similar planning activities quarter after quarter without learning or efficiency gains
• Tool Proliferation: Multiple attempts at process improvement had resulted in a collection of abandoned frameworks and tools, creating skepticism about new initiatives
• Dependency Blindness: Without shared planning language or timelines, teams struggled to identify and coordinate interdependent work

Strategic Framework

Phase 1: Diverge - "Understanding the Planning Ecosystem"

Comprehensive Process Discovery

• Analyzed planning artifacts from 7-10 squads (4-8 people each) across the rentals organization
• Conducted retrospective interviews with team members about what worked and what failed in previous planning cycles
• Mapped existing tool usage and process variations across teams
• Documented the full spectrum of planning approaches, from strict SAFE Agile implementations to ad-hoc methods
• Identified patterns of success and failure across different team compositions and project types

Key Insights Discovered:

• Teams were solving the same planning challenges independently, creating duplicated effort
• Lack of shared vocabulary made it impossible to understand capacity and dependencies across teams
• Over-detailed upfront planning led to wasted effort when priorities inevitably shifted
• Under-detailed planning created false confidence and missed critical dependencies

Phase 2: Define - "Crystallizing the Core Problems"

Problem Synthesis & Vision Development

• Synthesized research findings into core dysfunction patterns around timing, detail level, and coordination
• Identified the need for a flexible framework rather than a rigid process to avoid previous implementation failures
• Defined success criteria: reduced churn, improved velocity, better cross-team coordination, and maintainable planning overhead
• Established design principles for the solution: flexibility over rigidity, shared language over shared tools, learning-oriented over perfection-oriented

Strategic Positioning: Playbook vs. Process The most critical strategic decision was positioning our solution as a "playbook" rather than a "process." This distinction became central to our approach and ultimate success:

• Process Implies Rigidity: Previous initiatives had failed because they demanded strict adherence to prescribed steps, creating resistance when teams encountered unique situations
• Playbook Suggests Flexibility: A playbook provides principles, frameworks, and examples that teams can adapt to their specific context and needs
• Historical Context: Given Realtor.com's graveyard of abandoned planning processes, any new "process" would be viewed with skepticism and likely ignored
• Adoption Strategy: By emphasizing adaptability over compliance, we increased buy-in and reduced implementation friction

This framing shift was essential for overcoming organizational change fatigue and creating sustainable adoption.

Phase 3: Develop - "Creating the Shape Up-Inspired Solution"

Solution Architecture & Adaptation

Drawing from Ryan Singer's Shape Up methodology, we adapted key concepts for Realtor.com's quarterly planning context:

Core Framework Elements:

• Appetite Setting: Teams define resource constraints before solution design, preventing over-engineering
• Shaping Documents: Structured approach to defining problems and solution direction without premature specification
• Betting Table Concept: Regular decision points for continuing, pausing, or pivoting work
• 2 and 6-Week Cycles: Shorter feedback loops within quarterly planning to enable course correction
• Quarterly Cycle Planning: Teams plan a full quarter of cycles while maintaining flexibility for bi-annual deep planning

Playbook Structure:

1. Pre-Planning Phase: Appetite setting and problem shaping
2. Cycle Definition: Breaking quarterly goals into manageable chunks
3. Betting Decisions: Regular checkpoints for resource allocation and priority adjustment
4. Execution Tracking: Lightweight progress monitoring without micromanagement
5. Retrospective Integration: Learning capture for improved future planning

Phase 4: Deliver - "Implementation and Organizational Adoption"

Rollout Strategy & Change Management

• Created comprehensive playbook documentation with examples and templates
• Facilitated workshops with product management, engineering, and QA leaders to build buy-in
• Positioned implementation as experimentation rather than mandate to reduce resistance
• Established shared terminology and expectations while allowing process customization
• Created feedback loops to iterate on the playbook based on early adoption experiences

Key Contributions & Leadership

Strategic Design Leadership

• Co-led cross-functional research initiative to understand organizational planning dysfunction
• Designed adaptation strategy for Shape Up methodology to fit quarterly planning cycles and organizational culture
• Facilitated stakeholder alignment sessions to build consensus around new approach
• Created change management strategy that positioned playbook as flexible framework rather than rigid process

Process Innovation

• Applied design research methodologies to organizational process challenges
• Synthesized complex organizational dynamics into actionable framework
• Created replicable methodology for process transformation across different team contexts
• Established sustainable feedback mechanisms for continuous playbook improvement

Results & Impact

Quantitative Improvements

• Increased Velocity: Teams shipped larger, more cohesive pieces of work within planned timeframes
• Reduced Churn: Measurable decrease in mid-cycle priority changes and re-planning activities
• Improved Predictability: Better accuracy in timeline estimation and dependency identification

Qualitative Transformation

• Enhanced Focus: Teams reported greater clarity on priorities and reduced context-switching
• Better Coordination: Shared planning language enabled more effective cross-team collaboration
• Increased Confidence: Appetite-based planning gave teams clearer constraints and decision-making authority
• User-Centered Outcomes: Within rentals organization, teams shipped more coherent, user-focused feature sets

Organizational Adoption

• Immediate Success: Full adoption within rentals organization within one quarter
• Scaled Implementation: Key tenets adopted across multiple teams company-wide
• Language Persistence: Shared terminology became standard vocabulary for planning discussions
• Framework Durability: Core concepts continued to be used across Avail and other organizational contexts

Strategic Innovation

This project demonstrated several key innovations in organizational process design:

Playbook vs. Process: A Strategic Design Decision The distinction between creating a playbook versus a process became the foundational strategic decision that determined the project's success. This wasn't merely semantic—it represented a fundamental shift in how we approached organizational change.

Why "Process" Would Have Failed:

• Realtor.com had a documented history of process initiatives that were enthusiastically launched and quietly abandoned
• Teams had developed resistance to top-down process mandates that didn't account for their unique contexts
• Previous failures created organizational skepticism about any new "process" regardless of its quality
• Rigid processes often broke down when teams encountered edge cases or changing priorities

The Playbook Advantage:

• Principle-Based: Provided foundational concepts that teams could apply flexibly rather than steps to follow rigidly
• Context-Adaptive: Allowed teams to maintain their successful practices while adopting shared language and coordination mechanisms
• Learning-Oriented: Positioned as a living document that would evolve based on team feedback and experience
• Voluntary Adoption: Teams could choose which elements to implement and how, reducing resistance and increasing ownership

Implementation Strategy: Rather than mandating adoption, we created conditions for voluntary uptake by:

• Demonstrating value through early wins in the rentals organization
• Providing clear benefits (reduced churn, better coordination) without requiring complete process overhaul
• Establishing shared terminology and expectations while preserving team autonomy
• Creating feedback mechanisms to continuously improve the playbook based on real-world usage

This strategic positioning was crucial for overcoming organizational change fatigue and creating the psychological safety necessary for teams to experiment with new approaches.

Research-Driven Process Design Applied user research methodologies to internal process challenges, treating teams as users and planning as a product. This approach uncovered insights that traditional process consultation might have missed.

Shape Up Adaptation Successfully adapted startup-focused methodology for larger organizational context, maintaining core principles while addressing enterprise-scale coordination challenges.

Change Management Integration Embedded change management considerations into the solution design, creating higher likelihood of sustained adoption through careful positioning and stakeholder engagement.

Framework Replicability

A consiten design thinking framework proved essential for this organizational transformation:

Structured Discovery: Systematic research prevented assumptions and uncovered root causes rather than symptoms Clear Problem Definition: Synthesis phase created shared understanding of core challenges across stakeholders
Solution Validation: Iterative development allowed testing and refinement before full rollout Implementation Strategy: Delivery phase included change management and adoption considerations from the beginning

Long-Term Impact

Beyond immediate process improvements, this initiative established several lasting organizational capabilities:

Design-Led Process Innovation: Demonstrated the value of applying design methodologies to operational challenges Collaborative Problem-Solving: Created template for cross-functional teams to tackle complex organizational issues Adaptive Framework Thinking: Shifted organizational mindset from rigid process implementation to flexible framework adoption Continuous Improvement Culture: Established feedback mechanisms and learning orientation that continued beyond initial implementation

The success of this initiative validated the approach of treating organizational processes as design challenges, leading to its application in other contexts and contributing to a more design-forward approach to operational transformation at Realtor.com.

This project showcased how design thinking and research methodologies can transform organizational operations, creating lasting change through user-centered process design and strategic framework adaptation.