Design management

Background

In June of 2021, I became a design manager on our team, leading a team of 4 designers (now 5 including a content designer) across multiple condition areas. It’s been my first experience being a manager, and has been an incredibly rewarding challenge.

I took on this new role at a complex time for Omada. Earlier that year our product and engineering org went through layoffs, followed by more attrition that led to low team morale and a reduced engineering velocity. It also came during a time where many changes were in flight regarding our product development processes, and Omada was refocusing on a new vision for the future.

I took on the role with the primary purpose in mind to figure out how to best support the team navigating a difficult time, and to ultimately introduce processes and systems that would help us create great user experiences together.

Approach

1. Define my scope

Clarify the scope of my responsibilities with leadership and the team to ensure nothing slips through the cracks.

2. Identify opportunities

Spend time with team members and cross functional partners identifying the source of issues

3. Introducing experimental changes

Incrementally introduce small ‘experiments’ with the input of the team

4. Continually iterate

Create mechanisms for constant feedback from team members on whats working and whats not

Define my scope

This was my first time being a manager, and, I was taking on the new responsibility during a complicated time where I didn’t expect I was going to receive much hands-on mentorship.

To keep things manageable, I created a short framework outlining all the things I thought a design manager should do (at least as far as I’ve encountered from past managers, books, etc). The framework was meant to be a map of all the things I could be doing with my time to help me be clear about my areas of responsibility, be proactive rather than reactive, and to generally keep a broader perspective and not over-index on any one thing.

I reviewed this with my new manager to ensure we were aligned, then fleshed it out into a more finished framework that I’ve used as a guide ever since. I also wrote a blog post about it if you’d like to deep dive into my thoughts here.

From there, I broke down these two core responsibilities into sub-responsibilities, and then listed the further details for each sub-responsibility. I use this framework to ensure I’m thinking about the right things, and to avoid, as much as possible, blind spots I might have as a new manager in terms of where I could be creating impact. You can see the full framework summarized in this diagram below.

Identifying opportunities

When taking on a new role, especially a leadership role, the most important thing in my mind is to listen and understand everyone’s perspective in order to know how to best cultivate the team and enable high quality work. While I of course already had my own perspectives, I talked to everyone on my team about their hopes, fears, how they felt things were going, and more to get a good sense of where everyone was at and how they were feeling. I also talked to my new cross functional partners to learn more about how the design team was perceived and what we could do better.

Here’s some of what I heard:

Members of the team loved our team’s sense of community, friendship, and belonging, but felt that this was falling to the wayside during remote work. Team members cited this sense of community as a key reason why they loved working at Omada.

Members of the team felt frustrated by a lack of clarity from leadership. A history of shifting priorities, lack of clear objectives and metrics, and unclear thought processes had eroded trust with leadership and created confusion on teams. In the midst of so many changes, that lack of clarity was creating real issues.

Members of the team felt disempowered by our product development processes. They often felt like they were being handed pre-baked solutions rather than problems, didn’t have room to innovate, and that we weren’t connected enough to our user’s needs. They also felt that our product development processes lacked sufficient rituals and standardization, creating confusion and inconsistency between teams.

Our cross-functional partners generally loved working with our designers, but felt that they wanted to be involved in the product development process earlier and more predictably to ensure their voices were being heard at the right times.

Before jumping into how I acted on these insights, it’s worth noting that they all are, and always will be, a continual work in progress. Additionally, as I resolve old ones, new opportunities for improvement come up. Supporting a UX team, like building a product, is a constant iterative practice of identifying opportunities, prioritizing them, trying out small experiments and improvements, and measuring success. I wanted to highlight here just a few of the opportunities and problems I’ve worked on solving so far, but in reality, this is a never ending, cyclical process.

Prioritize and experiment with changes

Since I began this role, I’ve been chipping away at this list with small experimental changes, both within my team and across product and engineering through strong cross functional partnership. As I try things, I liberally ask for feedback from my team and peers, make changes, and keep updating the list of opportunities as I learn. Below is a sampling of some of the initiatives and projects I’ve done since taking on this role, that I’ve broken up into three main categories:

1. Fostering connection and community

2. Improving clarity

3. Strengthening our design and development processes

Fostering connection and community

At the top of my list was ensuring members of the team felt a strong sense of community, belonging, psychological safety, ownership, and motivation. These things, in my mind, are the core of a successful, happy, productive team - and are the highest leverage elements of a team to foster and maintain.

Team offsite: One of the first things I did was propose and plan a team offsite with our broader product org. The offsite focused on community building, reconnecting, and building clarity and shared understanding around key initiatives.

I partnered with my other product org leaders to create and lead a 3 day agenda with our product org, including plenty of social time for the team to bond!

In our end of year team retrospective, the offsite was the number one cited thing that people loved about the year. As said by one member of our team:

“Really enjoyed the product offsite and the cross-team collaboration that went on there. It was interesting to see what people are working on and how we all contribute to one larger vision”

Joint ownership & empowerment: I also began distributing ownership and responsibility of team initiatives (including the ones on this list). The team was doing some of this before I took on this role, and I doubled down on it for 3 main reasons:

1. Joint investment from team members fosters a sense of co-ownership and belonging. Members of the team own and lead our weekly standup, design crit, a book club, monthly social event, initiatives around improving our research practices, design quality, and more. We have a culture now where people feel safe to come up with new ideas that could make our team stronger, propose them, and make them a reality. I also still contribute of course as well, leading our weekly team meeting, proposing new ideas, and more.

2. The second advantage is that this model supplies more leadership and development opportunities for members of the team in a way that’s relatively adjustable with the ebb and flow of workload from other projects. They can simply maintain and continue to run their piece, or improve on it when they have capacity and are looking for a new challenge.

3. The third advantage is that the more the team is able to function autonomously, the more I’m able to focus my time on other problems that I’m more uniquely positioned to tackle. I see my role as creating systems that help members of my team be happy, productive, and successful. I’m most successful when they’re able to get great results in their work with minimal direct involvement from me.

Recognition & gratitude: I also heard in my initial conversations with the team that some didn’t feel like their contributions were being recognized enough and that they had been feeling under appreciated.

• One of the first things I did was restructure our team meetings to always include a ‘Shoutouts’ section where peers could highlight accomplishments and appreciation for one another. I also always make sure I had at least one shout out to give.

• I also began highlighting accomplishments from members of the team to the broader product organization and aimed to give them more visibility. I sent out thank you’s and shoutouts on large slack channels, and brought members of the team to share their work at the product all hands and other forums.

• Last, I lobbied our product leader for budget to get everyone nice gifts at the end of the year. I also wrote up a summary of everything each member of the team had accomplished this year and read them all out loud to the team at our last team meeting of the year.

Social events & team shirts: As I’m sure anyone reading this has also felt over the last few years, it is a lot harder to have fun team social events over Zoom. Even so, we introduced a monthly team social event, usually with some activity or theme. We also have a book club, and got one of the highly talented artists on our team to design custom shirts the further underscore a sense of community.

It’s no one thing that creates a sense of community and belonging. But together, these small changes, norms, and rituals that we’ve fostered as a group together have deepened the connections on the team. Beyond just improving morale and making Omada a fun place to work, my goal has been to create a safe space where people feel relaxed and empowered to play, take risks, try things, and be vulnerable with one another.

So far, our team has had zero attrition since I’ve begun leading it, while our PM, engineering, and clinical teams have all had significant attrition. Additionally, as you can see below, in our most recent engagement survey (6 months after me taking this role), key measures of our team’s psychological safety and sense of belonging were at 100% positive.

Improving clarity

I’ve also spent a significant amount of time aiming to improve clarity for my team. My goal is to ensure they’re empowered with the information and clarity they need to do their jobs well. This has been a challenging problem to solve, and is very much an ongoing goal of mine. I’ll walk you through what I’ve tried, what’s worked, and what hasn’t.

Close the information gap: This has been the easiest and most successful thing I’ve done. Part of the issue, it turned out, was simply that information was not reaching people on my team sometimes. After taking this role, I dramatically increased the volume of information being shared with the team and repeated things multiple times through multiple channels. I created more time for Q&A between me and the team, as well as inviting other leaders at Omada to come to our team’s meetings to directly answer questions and share thoughts.

Product vision work: Omada has been refocusing its priorities this year and our leadership has been working to ensure everyone’s on the same page about our priorities and company direction. As a part of that, I’ve been leading a project to articulate a vision for our member’s experience 3-5 years down the road to generate internal alignment and excitement about the road ahead. I partnered with another designer, clinical director, and product director to write a story of a member experience that represented our members problems and articulated the key themes outlined by our leadership for Omada’s future. We ended up with the high level journey you see below, highlighting key moments of our member’s journey of the future.

We then drew out each of these moments in more detail as a story with sketches to go along with it.

This artifact has been incredibly valuable, but not in the way I originally thought. We haven’t yet shared it out with the full team yet. When we shared it back to our executive leadership, we uncovered key areas in the vision that members of our executive team were not aligned with each other on. Work on the story was paused, as we’re planning a workshop with our executive team now to ensure we have alignment before moving forward.

By using stories and thinking about our company’s vision from the user’s perspective, our executive team was able to have a deeper conversation about their own views and uncover key differences. Resolving these differences and ensuring alignment before communicating the vision more broadly will be key to creating clarity for the company.

Strengthening design and product development processes

Finally, I’ve focused much of my time strengthening our team’s craft, educating about the role of design, and evolving our product development processes.

UX at Omada: From my initial conversations with both the team and our external stakeholders, I saw a need to clarify our role as a UX team at Omada. The goal was to empower members of the team with a shared point of view with the team on what role we wanted our team to play, and how we wanted to do it. I also wanted to help educate stakeholders about what they could expect from a UX team, and use this tool as a guiding light for future initiatives about where to develop the team and to create learning and development opportunities.

To do this, I partnered with one of our senior designers to lead the team through an exercise to introspect on the role we wanted to play at Omada moving forward. To drive the conversation, we used a survey I sent to cross functional partners for feedback, frameworks and models of design teams I researched and presented, and our own retrospective thoughts. The output, as you can see below, was this framework outlining our team values, what we do, how we do it, and what we achieve:

This framework is our shared team’s perspective on the role UX can play at Omada. It’s been an incredibly useful tool, and by being co-created, has built trust that we’re all aiming in the same direction.

I’ve also started using this as a guide for Craft Conversations. Members of the team expressed a desire to learn more from each other about best practices in design. Intermittently we host craft conversations focusing in on one of the ‘What we do’ topics - discussing what we think we do well, where we think we could do better, and creating an opportunity for individual members of the team to share where they shine.

Last, I also use this as a tool to help me guide where I’m focusing on developing new processes and systems for the broader team. For example, continue to read on to learn about how I’ve worked to develop our team’s ability to advocate effectively for our users.

Advocating for our users: In the last couple of years at Omada, projects aimed at solving problems from ground up user research and direct insights about user problems had fallen to the wayside in favor of more commercial driven, customer focused priorities. User research was often used as more of a tool to inform details within defined, solution oriented projects, rather than as a need-finding tool to identify new opportunities. For a B -> B -> C business like Omada - this can make sense at times, however we’d seen both engagement and member satisfaction begin to decline, and it was time to rebalance.

In response, I pushed for and sponsored two new initiatives to help revitalize a strong foundational understanding of our members and begin to solve user centered problems.

First, I partnered with our lead user researcher and another senior designer on our team and co-defined and sponsored a foundational user research study they would conduct to revitalize our understanding of our users, and to create simple, digestible artifacts such as personas, user journey maps, etc to serve as communication tools with the rest of the organization. The research was general need finding research, but focused on areas defined by leadership as strategic priorities, for example, understanding how co-morbidities affected patients with chronic conditions.

I also began a monthly review of member feedback surveys at week 16 of our program, app store reviews, and product related customer support tickets. All these sources were member data about our current program experience that were previously untapped. I partnered with another member who took the lead on running these monthly reviews and synthesizing the results into a quarterly report for our product team and leadership on what people were saying about our program.

Below you can see an example of one month’s worth of feedback after being parsed and grouped into categories.

I also worked in close partnership with our VP of Product to ensure this work could be fed back into the product team’s roadmap and we had a process in place to prioritize the opportunities we found against other priorities at Omada.

In sum, since taking this leadership role, I’ve focused on fostering connection and community, improving clarity, and strengthening our design and development processes. While I’ve seen promising signs of improvement such as increasing engagement scores, positive qualitative feedback from my team, peers, and leaders, and broad interest in new initiatives such as the member feedback reports, it is a constant iterative process.

Continually iterate

The work above represents a small set of the systems, processes, and projects I’ve worked on to enable great user experience at Omada. A team is constantly growing and evolving. Just like designing a product, designing how a team functions never stops.

Since I took over, our team’s engagement score is up 11% - a clear sign we are headed in the right direction.

I’ve learned so much since taking this role. In addition to our bi-annual company feedback surveys, I regularly run retro’s with the team, send out surveys soliciting feedback from the team and peers, and ask team members regularly how things are going and what they think we could be doing better.

Thank you for reading and please reach out if you’re interested in working together!