How to level up on product design leadership

January 26, 2019


7 min read

Leslie Yang
Leslie Yang
Product Design Director
How to level up on product design leadership

I didn’t go to art school or study design at college. I studied sociology at Berkeley because I wanted to work for social change. When I graduated, I found myself looking for both mentors and nonprofit work. (I’ll tell you how I got into product design another day.) One day, I responded to an email on a list-serve about joining a nonprofit leadership development group, which I did and became known as On the Verge. What I didn’t know then was that I’d wind up spending years after work and on weekends collaborating with young, emerging leaders to facilitate meetings and have hard conversations in groups. In a lot of ways, it was like getting a Master’s degree in soft skills. On the Verge taught me many things but here are three important lessons about building a brain trust:

1. Build a community or group of people that will reflect back their honest experiences of you. It’s not enough to surround yourself with friends and colleagues you hang out with after work. You need people who will be kind AND won’t hold back from saying you disregarded someone’s feelings, didn’t keep your word, or just plain messed up.

2. Asking for help isn’t a weakness. It brings you closer to people and you’re stronger for sharing and working through hard experiences.

3. Everyone is figuring it out as they go along. People in the 30s, 40s, 50s and beyond are also still learning and evolving. This also means there’s no one mentor, coach or leader that will have all the knowledge and advice to help you. We’re all knitting and remixing our lessons learned with advice we hear and read.

Today, as a design manager, I spend time building a learning community because management and leadership are now my craft. If I don’t constantly ramp up my experience, then I fail our design team by not growing. Just as I ask my direct reports to grow in soft skills and craft, I ask the same of myself.

Here’s my approach to being diverse and thoughtful in how I knit together a brain trust of advice and guidance from many sources and channels.

Look to your direct reports

At the end of every weekly one-on-one with my direct reports, I ask them, “Is there anything I can do better, more of, less of?” I usually get feedback that could be ideas for working differently as a team, that I didn’t clearly explain a certain idea, or that I didn’t follow through on an action item. I see feedback as qualitative research and their feedback or concerns as possible trends and pains across the team. From their feedback, I’ll look how I can improve my performance and/or co-create solutions with them.

This idea came from Manager Tools’ podcast. They have three quick episodes on 1:1s.

Look outside of your company

You probably have a very healthy to-do list. That means you may not get all the guidance you’d like or need from your manager, for they are likely as swamped as you are. So it’s beneficial to seek support outside of your company.

Take classes

Based in San Francisco, Design Dept is a great company offering leadership workshops for design leaders. I took their design leadership fundamentals workshop and found it incredibly valuable.

Mia Blume and her team covered topics like designing design teams, cultivating culture, how to give feedback, leading through difficult org changes, building resilience in your team, and more. It was also valuable to chat and compare approaches with design leads from Shopify, Dropbox, Instacart, Gusto, Thumbtack and other companies with various-sized teams. I highly recommend their workshops in San Francisco, New York and Toronto.

Build and maintain connections

It’s great to balance input from peers inside your company with input from those outside of your company. External perspectives are functionally objective and bank on multiple experiences and approaches.

I regularly schedule coffee dates and dinners with design leads and ask about their experience and strategies. When done with respect to the person’s time and experience, I think those I contact are happy to have a thoughtful conversation about leadership, a topic we’re both passionate about. Plus, I always buy them coffee or tea and make it easy by meeting where and when is most convenient for them.

Learn from experts

In addition to input you get from peers outside of your company, it’s also great to get help from more experienced leaders. If you feel stymied, or just want another perspective, it’s invaluable to have the support of someone whose career is built around helping you succeed.

Whitney Hess comes highly recommended for executive and design leadership coaching.

Plucky is Jennifer Dary’s consulting business for individuals and leadership teams.

Donna Lichaw is well-recommended for leadership coaching.

Design Dept also offers design management coaching.

Look beyond your profession

Design is relatively newer to the technology sector compared to engineering. There’s a strong overlap to being a manager in either profession. I’ve started to set up coffee chats with engineering leaders at OpenTable to ask about their specific experiences and strategies.

Look beyond your industry

I spent a decade in the nonprofit sector before I moved to tech. One of my mentors from On the Verge has been living #radicalcandor since the 1980s. She showed me how to be breathtakingly fearless at confronting people and situations when she sees a team isn’t addressing the real issues on a project or between team members. Yet you feel that she speaks up because she cares equally about the work and the people that do the work. I try to model the strength she shows and the love she has for her teams whenever I enter a hard conversation.

Out of a cohort from On the Verge, I also participate in a women’s group of nonprofit leaders and business owners that’s been meeting for over 10 years. We have dinner at each other’s homes once a month and share what’s happening at work and home. They remind me that almost everything I work on, from product to management, are people problems. And that regardless of our job titles and roles, we’re all just humans trying to do right by the people and communities we care about.

Look online

Slack and other communities

Leading Design is my favorite Slack workspace and is for senior design leaders. This is my happy place! This is where people who nerd out on design leadership hang out. I ask for and give advice here all the time.

Rands is also a good one that spans all tech leadership. Join the #leading-design channel.

Playbook is a unique way to surface advice for designers.

Start reading and listening

This could be a long list but here what’s been on my most recent reading list:

Extreme Ownership. Former Navy SEAL officers, Jocko Willink and Leif Babin, use war stories and business case studies to make a compelling argument for leaders to take full responsibility for their teams’ actions versus blaming others. The Iraq war stories frankly make me uncomfortable, but their lessons have helped me identify what values I want to grow in myself and others: acknowledging mistakes, accepting full responsibility, giving feedback, and reflecting on how to not repeat mistakes.

Dare to Lead by Brené Brown couldn’t have come at a more opportune time. In a world where there’s more blame than honest acceptance of feedback, we need to remind ourselves that there’s strength in vulnerability and receiving difficult feedback.

Resilient Management by Lara Hogan is a great primer for new managers.

High Output Management by Andy Grove is a timeless classic in helping you navigate the world of management.

The Making of a Manager is by Julie Zhuo, former VP of Product Design at Facebook, is a smart handbook for new leaders with a variety of advice from recruiting to how to give feedback.

Crucial Conversations is a must read by Kerry Patterson, Joseph Grenny, Ron McMillan and Al Switzler. I spend time helping my team practice how to give critical feedback, which is necessary regardless of role.

Radical Candor lives up to the hype. I initially thought this book was only about giving feedback, but it’s a fairly wide-ranging book about leadership. Our design team took this on as a book club and it has been a great conversation starter about feedback, design processes and more.

Other recommendations from fellow design leaders include:

Liftoff by Charles Avore and Russ Unger

The Manager’s Path by Camille Fournier

Turn the Ship Around by L. David Marquet

Harvard Business Review’s 10 Must Reads for New Managers


Designer Fund’s blog has a solid collection of articles on design leadership.

Shout out to Buzzfeed Design for sharing their documentation which has helped me level set on my goal of becoming a director one day.

Podcasts and videos by Invision is an excellent ongoing podcast with industry design leaders.

Hustle is the podcast of Funsize, an Austin-based digital agency. They chat with design leaders, designers, product leaders, agency owners about the evolution of design craft.

High Resolution is the product of Bobby Ghoshal and Jared Erondu doing 25 interviews with design leaders. Each episode is worth a listen.

Manager Tools is a management consultancy with a helpful podcast covering the in’s and out’s of management.

Leading Design is also a yearly conference held both in the UK and US. Here are their latest talks.

Progression is a podcast run by ex-design manager Jonny Burch with interviews of design leaders across the US and UK.

New Layer is a product design podcast from the dynamic duo, Tanner Christensen and Jasmine Friedl covering design careers, tools, education, critique, and more.

Share your learnings

These are all the ways I learn and collect insights and resources. I’m happy to share them because external support has made in huge difference in how I learn, feel supported, and support others.

So what are your strategies and approaches for building your design brain trust? I’d love to hear from you. Comment below and I’ll add them to the post.

Big thanks to Jennifer Bader for editing this post.


Author image
Leslie Yang (she/her/hers)
Product Design Director

Leslie Yang is a Director of Product Design overseeing product design for the restaurant side of OpenTable. She grows design leaders that work at the intersection of user value and business impact.