David & Mary Sherwin

Co-founders, Ask The Sherwins LLC


Grooming an Heir and a Spare

Tue 25 October 16

We spend so much time focused on doing what’s needed right now in service of great design: Take care of the day-to-day needs of the team. Hit quarterly milestones. Meet and exceed expectations all around. With so many decisions that need to be made hour by hour, how can you take the long-term view when you walk out of the office? Not just for your team, but for your life and career?

In this talk, we’ll focus on two questions that we hear regularly from design leaders, and that we’ve had to wrestle with ourselves: How do I start thinking about the long term, both for myself and my team? And how will I prepare my team to be successful if I’m not there?


Exploding Unicorns: Capability Mapping for Design Teams

Wed 26 October 16

Yet again, you’ve discovered the hard truth. Neither you nor anyone on your team is a unicorn, with mastery over all of the design skills in the universe. The work isn’t getting any easier. And there’s not a chance that the skills your team was hired for will still be applicable in ten years, let alone two. We just need to get better. At everything.

As a leader, how do you plan for growth, not just in headcount but in depth and breadth of skills? What’s your current picture of your team? What skills are you rich in? What ones do you need right away? Who is going to help develop them? And where do your skills fit into it all?

In this hands-on session, you’ll work with your fellow design leaders to:

  • Audit your team’s existing skill set: strengths, weaknesses, and everything in between
  • Identify what skills are critical to enhance and maintain for your team, based on your growth plan and company culture
  • Learn how to transition ownership of ongoing skills development to your team, and provide them with the necessary coaching and support

About David & Mary Sherwin

David Sherwin is a design leader, strategist, and teacher with deep expertise in developing innovation processes and training solutions for product teams and organisations worldwide. Most recently David led the product design team for, an online learning product used by millions of people worldwide (acquired in 2015 by LinkedIn). Before that, he was an Interaction Design Director at frog, where he led and coached dozens of large-scale product and service design teams, as well as helped to create training workshops for clients such as UNICEF, DARPA, and the World Economic Forum. He is the author of design bestseller Creative Workshop: 80 Challenges to Sharpen Your Design Skills and Success by Design: The Essential Business Reference for Designers. He advises frog as a Fellow on social impact, design education, and project-based learning initiatives.

Mary Paynter Sherwin is a seasoned writer, educator, and public speaking coach with expertise in helping individuals and schools develop rigorous curricula and activities for their learning needs. She has worked on multiple successful training programs and product innovation toolkits, such as Kaiser Permanente’s i60 Innovation Toolkit with Propelland and frog’s Collective Action Toolkit.

Together, David and Mary Sherwin are co-founders of Ask The Sherwins LLC, a consulting and training firm dedicated to helping leaders create design-driven teams and individuals gain the skills they need to solve complex challenges. They have worked most recently with Kiewit and MailChimp, and are hard at work on a book about how to create great workplace teams. For the past three years, they have been visiting professors at Copenhagen Institute of Interaction Design.