Top 5 challenges from design leaders at 2023 Leading Design Conference

Colleen Gao
November 22, 2023

On the 8th and 9th of November, the Askable UK team attended the 2023 Leading Design Conference. This event brought together over 200 design leaders from across the globe for two days of inspiring talks, amazing food and connecting with other global design leaders, all under the beautiful canopy of the Barbican Conservatory.

Whilst at the conference, the team facilitated an activity where we collected insights on two key questions; (1) what is a book that changed the way you lead? and (2) what has been your biggest leadership challenge this year?

In this post, we delve into five key leadership challenges that emerged from the conference.

Also read: Top 10 book picks from design leaders at 2023 Leading Design Conference

Managing team dynamics and growing teams

Leaders expressed that managing rapidly expanding teams was a prominent challenge this year. Some noted team growth from 30 to 60 members in just two months or transformation from one-man teams to teams of six or more. An inherent challenge in this growth was effectively managing team dynamics.

In his talk "Designing Direction" at Leading Design, Matt Davey, Chief Experience Officer at 1Password, delves into fostering a positive culture after scaling. If you’re facing team growth, his talk is highly recommended.

Strategic Communication and Alignment

Another key theme was the challenge of strategic communication and alignment between different stakeholders, especially at an executive level when product leadership is merged with another role or lost altogether, thereby losing sponsorship for product/design at the executive level.

In his talk "Amplifying design, reducing friction, easing the pressure", Teak Tse, Group Director of Design Systems & Operation at Sky, explores strategies for uniting design teams, fostering cross-functional collaboration, and nurturing team well-being. If strategic communication and alignment are current challenges for your team, his talk is a must-watch.

Leadership development and motivation/building trust in a team

Frequently referenced was the challenge of developing leadership skills to confidently lead teams, motivate them, and build trust. Particularly, helping designers to find their voices, have confidence in their decisions, and getting the most out of a team without burnout. This challenge was especially difficult for leaders in environments with low product/UX maturity or in teams that had been affected by mergers/layoffs.

In her talk "Building trust: A path for strong teams navigating through change", Līga Lētiņa, Head of Design at Printify, shares insights on building trust in a team during times of change. Additionally, Julia Whitney, an Executive and Leadership Coach, explores the power of emotional intelligence and vulnerability in gaining trust as a leader in her talk "Emotional intelligence: What I wish I’d known". Both talks are highly recommended for those facing challenges in leadership development and team motivation.

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Professional Growth and Transition

A significant challenge for new leaders was the transition and professional growth involved in moving from being an individual contributor to managing people. How do you develop the necessary leadership skills, lead a team well, and put their goals first without also neglecting your own?

Addressing this challenge, three compelling talks offer valuable insights. Maja, VP of Experience Design at TV 2 Denmark, shares her perspectives in "Navigating design leadership levels and spheres of influence". Temi, Product Design Leader at Instagram, explores the theme in her talk "Put your own mask on first", delving into the crucial aspect of self-care in leadership.

Lauren Currie, Founder of UPFRONT, also provides valuable insights in her talk "Designing with love; communities and power", where she delves into the intricacies of human connection, the sense of belonging, and the transformative power of community. Lauren's insights serve as a reminder that in the journey of design leadership, we are never truly alone, emphasizing the collective nature of this shared path.

Innovation and Quality Focus

Another challenge which emerged was the push for a focus on innovation and quality, particularly within teams handling backlogs full of features waiting to be implemented. A few leaders mentioned that getting huge teams of designers (some almost 90 designers) to do experiments in a certain way was a particular challenge.

In her talk "Raising the bar: Transcending the debate around quality", Payal Wadhwa, former leadership and VP at frog, explores how leaders can elevate the quality standards in their organizations. In terms of innovation, Ovetta Sampson, Director of UX Core Machine Learning at Google, discusses "Designing design leadership for an automated future", offering insights into what design leadership might look like in the future.

Our team at Askable found that many design teams were struggling to reach the desired level of quality in their product development and research, mainly due to budget constraints or bottlenecks in teams. One of our offerings, Askable Plus, was built to address this issue, allowing teams to accelerate product improvement and increase research capacity/efficiency.

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Colleen Gao

Head of UK

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