The Path to Design Leadership: A Recap from SF Design Week 2018

Bobby Zhang
Affinity
Published in
4 min readJul 6, 2018

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This year at San Francisco Design Week, we had the opportunity to chat with Andy Montgomery, Head of Design at Square Capital; Deny Khoung, Director of Design at 8VC; Faith Bolliger, VP of Design at SoFi; and Wesley Yun, Senior Manager of Product Design at Uber Freight on design leadership and how they got to where they are today. Here are some lessons we learned from them!

How are design management and design leadership different?

Design management consists of coaching, partnerships, advocacy, recruiting, and connecting the dots for design teams. A design manager is essentially responsible for building and maintaining his or her company’s design machine. From Uber Freight, Wesley described his role as making sure his team has constant clarity on projects and deadlines, recruiting, and ensuring everyone is producing at a high level of quality. Andy from Square Capital spoke to collaborating closely with fellow executives to define product strategy and a long term roadmap.

Design leadership, on the other hand, can emerge at any level in a company’s organizational hierarchy. A designer doesn’t need a big title to voice key design opinions, influence culture, or educate peers on what makes great design. Faith, from SoFi; and Deny, who collaborated with many startup design leaders in his directing role at 8VC; both described their approaches to design leadership as education around design and its value at all levels of a startup — from executives and managers in all departments to even the CEO. In their view, great design leadership comes from a combination of soft and hard skills to rally stakeholders around supporting good design as a fundamental value.

How do design leaders enable their teams to do their best work?

Designers are driven by different goals and interests that, in turn, influence how they bring out their best work. Wesley shared his framework for addressing this: by recognizing different archetypes of designers, such as “mavericks” and “architects.”

Mavericks are designers who are constantly hungry to build and move quickly. They thrive in environments that give them massive freedom and little convention or process to start. They’re excited by the idea of building from a blank slate and thrive at startups, especially at the onsets of their journeys. Architects, on the other hand, thrive designing scalable, reusable components by building on existing infrastructure. They’re more likely to do their best work at companies focused on crafting design systems that will truly succeed at scale.

Wesley cautioned that design teams can fall into the trap of hiring only designers of one archetype over others. Great teams are led by designers who are hyperconscious of their companies’ needs, and how many different archetypes fit into their projects and priorities.

Andy emphasized the importance of investing in scalable design systems and processes earlier than later. While they can initially feel like a burden for a design team itching to move quickly, this builds a foundation for everyone to do their best creative work in sync. At Square Capital, it created consistency and longevity for each designer’s work and magnified design’s overall impact at the organizational level.

Design as a Partnership

Designers tend to naturally gravitate towards other designers. But in thinking about creating great products, Andy and Wesley both emphasized that a designer’s primary partners should actually be his/her counterparts in product management and engineering.

Andy spoke to the importance of close cross-department collaboration on all fronts, from shipping design to recruiting. He encourages his designers to interact directly with their engineers and product managers to defend and debate their ideas. Andy also highlighted the importance of involving design in engineering and product recruiting: he personally plays a role in recruiting Square Capital’s engineers and product managers to vet for experience collaborating with and overall respect for good design.

Wesley warned that inconsistency and a lack of clarity between design and engineering/product leaders can lead to distrust within a company. If design leadership does a poor job of communicating constantly with its peers in engineering and product, it can breed a culture in which design regularly disregards engineering constraints, or misunderstands how the end user will truly think.

Faith emphasized the value of identifying individual strengths and weaknesses in building design partnerships. At a great team, individual contributors and managers are highly aware of and constantly building upon each other’s strengths. At the same time, they constantly are identifying their shared weaknesses and hiring people to fill in those gaps. These differences between designers can lead to tension, but Faith encourages her designers to welcome that tension and be comfortable navigating around it.

Thank you to all of the San Francisco Design Week organizers, our attendees, and our amazing panelists for making Affinity’s first SFDW event a huge success!

If you’re interested in learning more about what we’re up to at Affinity, come check our website out at affinity.co.

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