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Change is inevitable, especially in the fast-paced technology industry. Whether it's adapting to business pivots, technological shifts, team restructuring, or even something as simple as adjusting the frequency of team social events, leading through change requires thoughtful consideration and strategic approaches.
General Principles to Follow
1. Model the Behavior You Want to See
Your team will mirror your emotional response to change. As a leader, ensure your reaction and delivery align with the response you want from your team. Sometimes, this means explicitly sharing your feelings about a situation and acknowledging the expected emotional impact.
2. Provide Clear Direction
During periods of change, team members need explicit guidance. They should understand exactly what actions to take—or whether to maintain their current course. Eliminate ambiguity by outlining specific next steps and expectations.
3. Maintain Maximum Transparency
I've consistently found that being honest with team members, to the fullest extent possible, builds trust and resilience. Transparency helps teams navigate uncertainty more effectively and fosters an environment where questions and concerns can be addressed openly.
During the UX@CVS design conference, where we chose change as our theme, I reflected on my experiences leading teams through various transitions as Director of Product Design. These stories illustrate how these principles play out in real-world scenarios.
Changes in Policy
Problem:
At Oak Street Health, we faced a fundamental challenge when The Center for Medicare and Medicaid Services (CMS) announced significant changes to their risk-score methodology. These changes weren't minor adjustments—they involved eliminating certain diagnoses entirely and reweighting others, directly impacting our revenue stream. The obvious solution might have been to introduce a new tool with comprehensive training, but our providers and scribes were already struggling with their daily workload. We needed a solution that would ensure accurate diagnosis coding while being mindful of our teams' existing capacity.
Solution:
Instead of disrupting workflows with a new system, we chose to enhance our existing suspects system, which used artificial intelligence to predict patient conditions. Through careful analysis, we identified several key pain points in the current system: the suspects lacked specificity, documentation sources were insufficient, and similar suspects weren't properly grouped in the interface, making them time-consuming to scan.
We implemented a strategic, gradual approach to improvement. Over five months, we rolled out three smaller updates before introducing a larger interface modification. The first phase focused on reorganizing suspect data presentation, followed by revamping our tagging system, and finally implementing a more intuitive grouping structure. This measured approach allowed teams to adapt gradually while maintaining their productivity.
Lesson Learned: The Power of Familiarity
This experience reinforced a crucial principle: evolution outperforms revolution when it comes to organizational change. Building upon existing knowledge and workflows proved far more effective than forcing teams to start from scratch. The success of this project demonstrated that even significant changes can be implemented smoothly when they're rooted in familiar processes and introduced incrementally.
Changes in Platform
Problem:
A significant challenge arose when our product strategy shifted to moving all call center workflows to Salesforce. After several unsuccessful attempts by other teams, my design team was brought in to address major issues.
This transition required our team to learn an entirely new design language and collaborate with a different team operating under different constraints. The situation became particularly pressing when Oak Street signed an MSO contract with Aetna to manage post-hospitalization care for an additional 130,000 members. Due to time constraints and perceived limitations in customization, the initial Salesforce implementation was created without design involvement, resulting in poor adoption by the Transitional Care Coordination team.
Solution:
Our initial attempts fell short because we approached Salesforce with the same mindset we used for our existing Canopy platform. We discovered that simply completing Salesforce design courses wasn't sufficient—we needed a deeper understanding of our Salesforce team's capabilities and limitations. This realization led us to return to fundamental design principles, emphasizing how understanding user needs should drive information hierarchy, regardless of platform constraints.
Lesson Learned: Beyond the Surface
This experience taught us that true design excellence isn't about visual polish—it's about deeply understanding users and thoughtfully organizing information within given constraints. Sometimes, the most effective solutions come from working within limitations rather than fighting against them.
Changes in Product
Problem:
Our charts product navigation had become unwieldy over time, necessitating a shift from tabs to horizontal navigation. Despite the clear need for change, this update faced resistance: Product Managers worried about user confusion, while Engineers were concerned about the effort required for what seemed like a minor improvement. Basic usability principles weren't enough to convince stakeholders of the necessity for change.
Solution:
We developed a comprehensive approach to build stakeholder confidence:
1. We had an engineer create a functional prototype to identify potential issues early
2. We conducted thorough usability studies and documented various navigation iterations
3. We compiled all our findings into a compelling final presentation
Throughout the process, we consistently reinforced the necessity of the change, ensuring our message remained clear and constant.
Lesson Learned: The Rhythm of Adoption
The experience highlighted that meaningful change requires three key elements: consistent repetition of the message, continued exposure to the proposed solution, and proactive management of stakeholder concerns.
Changes in People
Problem:
As our product and engineering teams expanded, the design team needed to grow from 11 to 20 people. This growth necessitated adding a new layer of design managers—a significant structural change for a previously flat organization. The challenge was maintaining our tight-knit team culture while integrating this new management layer. The situation became complex when designers exhibited uncertainty about interacting with their new managers, leading to emerging trust issues that required immediate attention.
Solution:
I approached this transition methodically, beginning with clearly defining the distinction between our existing design lead role and the new design manager position. To ensure clarity, I created custom visual materials to illustrate these differences, followed by separate presentations for the team at large and the incoming managers.
When onboarding the new managers, I emphasized preserving and enhancing our existing team culture. Each manager was encouraged to propose cultural initiatives, leading to the implementation of book clubs, guest speaker series, improved annotation processes, and updates to our design system. By bringing all managers in simultaneously, we created a built-in support network for the new leadership layer.
Our initial attempt to organize teams by domain for design reviews and social events proved counterproductive, leading to silos. We quickly adjusted our approach, implementing more frequent full-team gatherings. Throughout this process, we maintained an active feedback loop with the team, allowing us to address concerns and adjust our approach in real-time.
Lesson Learned: The Human Element
Leadership transitions succeed when they combine active involvement, continuous feedback channels, and an appreciation for diverse management styles. The key is to balance structural changes with maintaining the cultural elements that make your team unique.
Changes in Partnerships
Problem:
To meet aggressive business deadlines for converting Canopy 1.0 modules to Canopy 2.0, we needed external support beyond our engineering capacity. We engaged Thoughtworks as our implementation partner, but faced the challenge of integrating an external agency into our established system while maintaining our quality standards and design philosophy.
Solution:
We developed a comprehensive integration strategy starting with a thorough onboarding process. This included a platform overview, introduction to our design system, and detailed guidance from our lead UI designer. Rather than relying solely on weekly stakeholder meetings, we instituted pair-designing sessions and regular design reviews, effectively embedding Thoughtworks team members within our daily operations.
The results exceeded expectations—the final check-in flow felt seamlessly integrated with our existing products because, in many ways, it was co-created by our combined teams working as one unit.
Lesson Learned: The Extension of Team
Successful partnerships require treating external collaborators as true team members rather than vendors. Integration into your culture and adherence to your standards creates alignment that produces superior results.
Changes in Process
Problem:
We faced a recurring issue where designers invested weeks or months in projects that either weren't prioritized or were pushed to later quarters. This pattern led to designer burnout and frustration over seemingly wasted effort. We needed to align our design process more closely with product prioritization while maintaining our ability to influence product direction.
Solution:
We restructured our design process into two distinct phases: concept design and detailed design. The concept phase focused on stakeholder alignment and rapid prototyping, allowing us to validate directions before investing in detailed design work. We also enhanced our collaboration with Product Managers by:
Supporting problem framing and validation
Facilitating stakeholder alignment through targeted activities and research
Creating concepts to inform roadmap prioritization
Conducting generative research to understand workflows and mental models
Initially, designers expressed concern about the new requirements, perceiving them as additional work. However, we helped them recognize that many of these activities were already part of their process—we were simply making them more intentional and visible.
Lesson Learned: The Power of Purpose
Process changes require clear communication of the 'why' before the 'what.' When team members understand the purpose behind changes, they're more likely to embrace them.
All Together
Leading through change has taught me valuable lessons that I continue to apply in new situations. These experiences remind us that successful change management requires:
Building on existing knowledge rather than starting from scratch
Focusing on user needs and information architecture over visual polish
Maintaining consistency in message and exposure while managing anxiety
Embracing diverse management styles while keeping active feedback loops
Treating partners as team members rather than external vendors
Leading with purpose and clear communication
These lessons serve as guideposts for future transitions, helping ensure that change, while inevitable, can be navigated successfully with the right approach and mindset.
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