Five Lessons From Leading

CEO Jocelyn Wyatt reflects on valuable lessons she learned on the job.

As she steps out of to begin her next chapter at Alight, CEO and cofounder of, Jocelyn Wyatt shared some of the lessons she’s learned in her ten years of leading We thought we would share some of them with you:

When I co-founded in 2011, I never expected this organization would grow to 70+ people across three locations or that the solutions we designed would impact the lives of 68 million. It’s been a formative journey to grow this place alongside incredible partner organizations, but when I think back at the most valuable things I’ll take away, aside from lifetime friendships and community, it’s the lessons learned.

1. Invite others into your learning journey—messiness and all.

      When we were putting together our five year impact report in 2016, a lot of our efforts were put into sharing our wins. There were all these splashy pages showing what we’d achieved. But when people talked about the impact report, the section that resonated the most with them was that of our five fails. This simple two-page spread outlined five lessons we’d learned in the past years. Readers appreciated the vulnerability of owning up to our mistakes and missteps. There’s also often more generosity in the lessons gleaned than in the wins. As a leader, I’ve worked hard to hold myself accountable to sharing both wins and failures and as I thought about what to talk about in this last message to you, I knew I wanted to share lessons I’ve learned along the way—often the hard way.

      2. Our impact is as deep as our process.

      Many years ago, when we were designing Asili, a social enterprise in Eastern Congo, we all wanted Asili to be designed by the women who would be running the water points, the health clinics, and the agriculture coops. We recognized that interviewing them and then going back to San Francisco to design the services and the brand was not going to lead to a successful, self-sustainable social enterprise.

      Co-design was a term we’d heard though we hadn’t actually practiced it before. I remember this was one of the first times we actually created the conditions for others to not only inform but also help guide the design process. We created games, role plays, and activities, then worked closely with a group of women in Kabare to co-create the service offerings, brand, and membership structures that would actually be resonant with them.

      Today Asili has water and health services that are continuing to operate two years after their grant funding ended. When the former CEO of Alight, Daniel Wordsworth returned to Congo, he met a woman who said “You might remember me. I was one of the people who designed Asili. And you see that blue in the logo, that was my idea. I told them it should be blue and there it is.” I truly believe that Asili is successful because it was designed by the women of Congo. This is why we've prioritized advancing our practices around co-design in the years since that Asili project.

      3. Play allows us to show up to the work untethered and optimistic.

      As a nonprofit organization, we often think we need to be really serious to do really serious work. I’ve come to learn that if we’re going to do creative and impactful work, we have to value joy and play along the way. At, I’ve seen some of the most elaborate, over-the-top pranks and creative warmups—from the April Fool’s we launched “Design Kat: The Guide to Cat-Centered Design” (a play on Design Kit) to the countless times we made up ridiculous games, solutions, and futures in order to make way for real ideas. For a year I didn't attend ‘Make Believe Time’ (a session devoted to imagination and craft in the New York studio), because I always had something else going on. Finally one of my colleagues pulled me aside and said “It's really important that you show up from time to time. It gives the rest of us permission to prioritize this too.” Activities like these give people the opportunity to tap into new ways of thinking, get tangible, and take themselves a little less seriously. I think that when this culture was most alive in our studios, we were able to design from a place of more abundance and optimism.

      4. We're all responsible for shaping the culture we want.

      In 2015, a set of us moved to New York from San Francisco, and needed to quickly hire many more people into the organization. We soon found ourselves in a situation where the majority of the team had been with for fewer than 6 months. We were having a really hard time coalescing our culture and getting the team to adopt our organizational values. A set of us decided we needed to explicitly model the values we hold dear more explicitly. We started holding design reviews in the middle of the studio—building on what others were saying and visually representing our ideas. We introduced a session at weekly studio meetings where we highlighted one of our values and celebrated colleagues who had demonstrated it that week. This is something I frequently share with rising leaders at there’s no us and them here, “the man” doesn’t exist at this place. If you see something that needs to change here, you need to be part of the solution.

      5. If we take confident strides to do the work you think is right, the rest will follow.

      For many years we took on so many projects related to adolescent reproductive health. I think it was 16 projects in 13 countries with 5 partners. Time and again we saw that adolescent girls had a set of interconnecting needs. In order to address transactional sex, girls needed other ways to make money. In order to prevent unwanted teen pregnancy, girls needed effective health education. But because of the ways our projects were funded, we had little ability to design for these intersecting needs.

      After taking some time to reflect on our AYSRH work as a whole we decided we’d try to proactively fundraise for a CoLab which would allow us to work in a more intersectional way. We knew this idea held promise to fundamentally shift the experience for girls and invite them in as drivers of the design process, however making the case for it in a sector defined by sector silos was an uphill battle. But we stuck it out, built this holistic approach into the core of our strategy, and did the legwork to find funders, partners, and collaborators who were willing to take the leap with us. The CoLab has allowed us to do that by tackling challenges girls face related to sexual health, wellbeing, and economic opportunity.

      I’m so proud to have played a part in shaping this organization and look forward to seeing all that it will accomplish next. To my community at, I hope you continue to be generous with each other, our partners, the world, and yourselves; that you stay optimistic and always believe in a better thing; and finally, that you have fun—it is a privilege to do meaningful work with people you love.