3 Designers Reflect on Leading Design 2022

Nora, Corey, and I recently attended the 2022 Leading Design conference. We wanted to share what we learned from the conference about ourselves, leading teams, managing individuals, and guiding growth in their career paths, and what we need as leaders. Some of us are individual contributors, some are managing leaders — but whatever leadership path you’re on as a designer (or in any field), we hope our takeaways inspire you.

—Andrew Possehl, Lead Product Designer

Nora Vanni

Lead Product Designer

How to C-level

One of my favorite talks of the conference was from Cap Watkins, chief experience officer at Primary. He spoke all about how wildly the responsibilities of a C-level design leader depart from the day-to-day of designers as individual contributors. As a lead-level IC myself, this was super fascinating because I had no idea what design executives actually have to worry about.

“Should you become upper management? How annoyed are you?” asked Watkins. How much do you want to get your fingers on the spreadsheets, make hard decisions, and operate from that higher altitude? This was a fascinating peek behind the curtain of the C-suite. I’m still happy about the lower altitude of my current role, but it was interesting to get a glimpse into that other plane of existence in our industry.

Prioritizing personal values

Many of the presentations focused on introspection and critical examination of what fulfills us most as design leaders. Speakers highlighted their personal crises of confidence in their current roles after all the upheaval during the pandemic. They also highlighted how this is a rare opportunity to shed the bullshit and only carry forth what works. Keep what energizes you, fulfills you, and has a positive impact on the world. Alice Quan (director of UX, Google) described it as the Japanese philosophy of ikigai: that which gives your life worth, meaning, or purpose. That sweet spot comes at the intersection of What I Love, What I’m Good At, What the World Needs, and What I’m Paid For.

On that note, one of the most profound sessions of the week was from Dianne Que (head of product design operations, Zendesk), entitled “A Meditation on Radical Inclusion.” She spoke from the heart about how she advocated for a greater investment in diversity, equity, and inclusion after the Black Lives Matter protests in 2020. Que emphasized how leadership in those moments looks like vulnerability, leaning into ambiguity and often getting things wrong, but it’s absolutely essential that we face that personal discomfort to uplift disadvantaged communities in our workplaces.

Enabling collective leadership

Haley Hughes (design director, formerly IBM, Airbnb, Shopify) spoke about building a team structure in which peers operate across a “Team of Teams,” rather than a typical top-down command structure. She believes that messy relationships and redundant systems across teams create resilient, creative companies. They don’t operate at peak potential efficiency, but they move with a shared purpose and create more opportunities for innovation. I appreciated this distinction: By leaning into riskier swings, and not worrying too much about minutiae, product teams can have a greater impact.

Andrew Possehl

Lead Product Designer

Being intentional in your career path

Many of the talks at the conference dealt with “The Great Resignation” and making sure you are serving yourself and others well in your role. Abbey Smalley, head of design programs at Amazon, urged us all to take stock each day of how we feel after every meeting, activity, and task. Where do we feel the most energized? Where do we feel the most drained? This is a great way to begin to learn whether our current role is best for us.

Embracing remote or hybrid work

Over the past two years, many people have had to adapt to a new way of remote and hybrid working. It was surreal to be back with other designers in the same room, sharing the same IRL experiences. Many of the talks emphasized making sure that employees feel supported and heard during this cultural shift in the workplace.

There was also an emphasis on cutting out unnecessary meetings. I think we all go through periods of meeting fatigue and need to be aware of how this can affect those around us. Cap Watkins, CXO at Primary, talked about how Primary instituted a four-day workweek for all employees. He said one of the more surprising things about this change was realizing that his own output and productivity stayed the same as when he worked five days a week.

Don’t model burnout

One of the themes of the conference that stuck with me was burnout. It can happen suddenly and without warning and be a very hard thing to recover from. It is so important, especially as leaders, to recognize the signs of burnout and take proactive steps to avoid it. When leaders are burned out, everyone feels the effects. It’s essential to make time for yourself and your personal needs if you are going to successfully lead others. As leaders we also model the culture we want to help create. By showing that we care for ourselves and our needs, we are fostering a healthy workplace for those around us.

Corey Roth

Lead Product Designer

Designing design teams

Peter Merholz’s talk on “The Evolving Design Leader” has me excited to talk more with client and agency-side leadership teams about diversifying our manager roles and how we can lead more effectively with cross-functional initiatives. His different leadership mindsets of Coach, Champion, Diplomat, and Architect shifted my thinking about leadership and encouraged me to think beyond my immediate reports and consider where I need to direct my energy at any given moment. As managers move up the ladder, they need to spend more time focused on areas outside of their team. This is a bit of a paradox, as their organizations are looking to them for leadership. It’s a leadership skill to know how to balance internal and external efforts.

Holding space for one another

During the Q&A for Dianne Que’s talk on radical inclusion, one shared experience stood out to me. I was struck by the story of someone’s direct report, who said, “I don’t want to go back to the office. I feel safe in my home. I don’t feel safe in the office.” Working from home means we’re all invited into one another’s kitchens, living rooms, and personal spaces. We have to hold space for one another, recognize opportunities to be empathetic when someone brings their whole self to work, and encourage everyone to build trust and vulnerability in ways that promote healthy working environments.

Creating space for myself

One of my overall takeaways from the conference was that leaders have to remember to put on their own oxygen mask first. If leaders don’t create safe spaces for themselves, they can’t expect their teams to feel they have that space. This is a tough but important lesson: Your team’s way of working is modeled in part by your way of working. If you’re working long hours, acting like a martyr in meetings, sending Slack messages while on vacation, and showing up to meetings crabby as a result, your team might begin to take on those habits too.

Nora Vanni (she/her), Andrew Possehl (he/him), and Corey Roth (he/him) are Lead Product Designers at Postlight. Reach out at hello@postlight.com.

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