Quarantine Diaries: Alana Washington

Design Dept.
Within Community
Published in
7 min readDec 16, 2020

Nine months into the COVID-19 pandemic we are collectively and individually grappling with being asked to halt our lives. From cancelled events to new work environments to social unrest, 2020 embodies the word “unprecedented”. Yet here we are adapting the best we can in the face of so much uncertainty.

As much as we all (I’m sure) would like to throw 2020 in the trash, there’s always room to see the silver lining as we begin to reset and prepare for 2021. This is why we created this new series called Quarantine Diaries.

Quarantine Diaries invites you into the life of fellow industry leaders as they share their stories of figuring out all that is 2020. It is our hope that from each story you can be reminded of your own value and resilience.

Alana speaking at the 2019 Fall Within Retreat for Emerging Leaders

Each week Alana Washington, Uber’s Head of Shipping Experience Design relishes in a moment of stillness as she observes the Jewish tradition Shabbat. Alana calls this her “clean break every week” that allows her to live in the moment, in a year that has been anything but quiet and restful.

Alana has spent years working in the fields of organizational psychology and design operations. Now she is in design management which makes her particularly well suited to weigh in on this moment. From the future of how we work, to how Design Ops folks can move the design industry forward, Alana’s words are the balm to the designer’s soul. Welcome to the Quarantine Design Diaries.

Q. 2020 has been insane. From the upcoming election to the racial tensions in our country. It’s been a heavy time. How have you been? How are you coping with everything going on in the world?

Alana: I have to scope that question for each day. When people ask, I’ve started to respond to that question with ‘I’m doing ok as far as 2020 is concerned.

The upside of this year has been that friendships, partnerships, and relationships at work are stronger than ever because we have all had to bond through something incredibly rough. I feel very fortunate that the work I’m doing at Uber Freight is directly related to supporting the continuation of commerce. We design experiences to support truck drivers — the true unsung heroes of this year — and Shippers — small to large businesses keeping our goods distributed, and shelves lined.

Q. You and your family practice a weekly Shabbat. How has that been helpful to get you and your family through this pandemic? What lessons can other design leaders take from this personal practice?

Alana: It’s such a clean break at the end of each week. However far you’ve gotten is how far you’ve gotten. I take that time to not design or think about processes. Practicing Shabbat spreads time out and makes it more luxurious. When you notice time can move at a slower pace there’s more possibility available to you.

Design leaders can create their own practices that allows them to ease into flow and really be in the moment. Personally after each week practicing Shabbat I found that I’m a more creative human come Monday. But, like anything, it is a practice. We’re great at it some weeks — others we let slip. Each week is an opportunity to try again.

Q. Tell the readers a bit about your background and career path. Any Interesting highlights you would like to share?

Alana: My background spans over several fields like design, strategy, and research. I got my start at HBO working in organizational development — pairing organizational challenges with strategies to support them (think team building, Director and VP leadership programs). I became fascinated with thinking about how to organize information so adults could retain information. I fell down the rabbit hole of information design and realized that while I loved that work I I had more interest in Design which led me to where I am today.

My career path hasn’t been linear. It’s been a series of saying “yes” to new adventures. That series of “yes” has resulted in a tapestry of experience that I am so lucky to pull from.When I am looking for my next challenge I ask myself :

  1. Is this problem interesting?
  2. Is this team exciting and filled with interesting humans who are ready to do the work?
  3. Am I contributing to creating a culture that begets equity and joy?

This is the foundation of everything I do. It’s my personal checklist for accountability.

Q. What’s it like leading your team through such uncertainty?

Alana: I have gotten through this (pandemic) by treating others the way I would want to be treated during a year like this truly unprecedented one. As leaders we must be vulnerable with our teams and acknowledge when things are going haywire outside of work. I try to lead with as much as my authentic self as I can.

Q. What’s your leadership style?

Alana: It fluctuates depending on what people need. I lean into Kim Scott’s methodology of Radical Candor — caring personally and challenging directly. I also index heavily on cohesion and collaboration. I love the Gwendolyn Brooks quote, “we are each other’s harvest; we are each other’s business; we are each other’s magnitude and bond.” Designers come to teams to work on challenging problems. They also come to organizations and teams to grow their skills by working alongside one another. I’m constantly thinking about the whole, about our team as a network, and how our efforts are magnified by the ways we work, learn, and grow together.

I believe we all have ownership and the capacity to nurture our organizational culture — the type of team we have and the creative practice we want to be in. So I encourage people to show up as their authentic self and to do so as an act of permission, of encouragement to the greater team to show up fully too. I truly believe my team’s success is my success.

Q. What advice about leadership would you give yourself 10 years ago?

Alana: Sometimes I questioned if obsessing over details like typography and line width was wrong. What I’ve learned as I’ve grown in my career is that it’s ok to obsess over craft because as you climb that ladder you have less time to focus on those things. I long for a meeting-free day now to throw on headphones and produce work (other than decks 😂).

Q. It seems like now is the time for the Design Ops field to use their expertise and apply it more broadly outside of design. How do you see this moment improving the future of work?

Alana: The true strength of Design Operation practitioners is that they parachute in and collect sentiment and figure out the biggest pain points challenging organizations and impeding progress.

Sometimes that pain is located in product teams that then trickles down to design. Other times it’s understanding the value of design and evangelizing that to leadership. Strong Design Ops folks have the savvy and experience to influence for the better.

Q. You speak a lot about showing up as your authentic self. What would you say for POC’s who are having a hard time showing up as their authentic self?

Alana: I want to acknowledge the privilege I enjoy because of my time in this industry, my role, and my network. There were times when I couldn’t show up authentically and it did work against me when I tried. I also have learned when to leave for greener fields and to take my brain trust where it’ll be appreciated.

For POCs entering new orgs, it’s okay to be slow to trust. Find your community and find your safe spaces. Organizations should work to earn your trust over time. Find helpers who can help you navigate office politics, understand the spoken and unspoken parts of your organization’s culture, and when you feel as though you have trust and a degree of safety, start paving the way for those who come after you.

Q. What is currently bringing you inspiration?

ALANA: I’m stoked about the work that I’m doing right now. I get an opportunity to envision with my team what the future for shippers will look like five years from now.

But I’m also inspired by getting out into nature, going on hikes and long walks. It’s been really nice these past few weeks.

Q. What does it mean to be a senior thought leader at this time?

ALANA: What is really magical is seeing my cohort also advancing. Chatting openly about what are the trends we’re seeing and what are the pain points at all levels of organizational maturity — I think there is a power and excitement in that.

I benefit from having two communities, DesignOps and Design management community. The cohort effect helps me preempt what’s around the bend and what we can do together to make our orgs better.

Q. What’s next for the future of work for design managers?

Alana: It is the same pain that everyone is going through. How do we do this whole design in a distributed way? What is the future of work?

One of the reasons we like to be in an office is that we could all cramp into a conference room and jam. However our reality currently is that those are use cases that we should be designing around — we should be social distancing, not jamming. So then what is the value of being in an office and gathering together? How do we make sure we capture that value while protecting each other? I don’t think I have the perfect answer but those are things I’m thinking about.

Q. Feels like we need a bit more love, compassion, and hope right now?

I’m hopeful for so much. I’m hopeful for this time galvanizing us to see humanity in one another. I’m hopeful to live in a world where more seamlessly we can be the same person inside and outside of work.

This spring amidst all the social justice initiatives and the responses I have seen from companies — something feels different. It feels like companies are making some real declarative steps forward and I’m hopeful the action they take will be positive and have a positive impact. So then I’m hopeful that there is a chance for a future of more hope and equity and joy for all of us.

Written by Ashley Glover for Within.

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