Coaching

I have two design system coaching offerings: virtual coaching for design system leads or teams and coaching cohorts for individuals looking to build a small community of like-minded learners.

Virtual Coaching

Because every individual and organization has unique needs, I’ve created a structure to follow that acknowledges the cultural challenges of design system work while also allowing room to dive into specific questions you may be facing.

My virtual coaching comes in five-week blocks (one 60 minute conversation each week). We'll communicate prior to these meetings so we can both be prepared. These conversations will feel structured but fluid. I'll ask you a lot of questions and we'll decide together on some form of next steps.

I've also developed a group coaching approach for when your whole team would like to participate. This is also offered in five-week blocks, and the pricing is dependent on the number of participants.

Currently, I have virtual coaching openings for Q2 and Q3 of 2024. Please reach out if you would like to learn more.

Between these conversations, we’ll communicate via email and a shared Google Doc or FigJam board. As part of the coaching effort, we'll stay in touch throughout the week. I’m happy to have informal conversations between our formally scheduled calls to process current happenings.

My goal will be to challenge and broaden your perspective on the design system effort. Together, we'll make sure your organization’s approach to the system is healthy for the specific context you’re operating in. To do this, we may talk through concepts like:

Often, individuals are looking for a combination of design system coaching and career coaching. My approach works well in these scenarios. My experience as someone working in the tech space for over 20 years—founding companies, leading teams, hiring—offers a valuable perspective to many in their early or mid-career journey.

Coaching Cohorts

Coaching cohorts are small groups of like-minded learners gathering weekly to share their experiences and learn from each other on a specific topic. Cohorts typically run for five weeks and use Discord and FigJam as the primary tools for collaboration.

Each week begins with 15–20 minutes of check in, followed by a short presentation from me about a specific topic, and concludes with a conversation diving into the details of how the week’s concept plays out in the real world. After each virtual conversation, you’ll have some homework to do. During the week, we'll discuss the homework in our Discord channel.

Cohorts are fantastic for individuals looking to learn from the experience of others. We focus on growing in our understanding of big design system concepts, but also on getting to know each other. A cohort is an intense season of growth and community-building.

I offer each member of a cohort a free one-hour consultation after the cohort is complete. This is a tremendous way to address any specific questions you have or to gather a bit more information on how to apply the concepts covered in the cohort. Truthfully, we can use this time however you'd like, so there is flexibility in the approach.

Design System Cultural Analysis Cohort

The DS Cultural Analysis Cohort is a deep dive into the impact an organization's culture has on the sustainable approaches to a design system program. We'll begin with an overview of the research I've conducted in this area over the last three years. Then we'll dive into using the model of analysis on ourselves, our DS team, and our subscribers. Finally we'll conclude with an opportunity for you to share back your learning. If you feel like you're swimming against the tide or if you want to find a group of like-minded design system learners, this may be for you.

Design System Maturity Model Cohort

The DS Maturity Model Cohort is a deep dive into the design system maturity model I've developed over the last four years. We'll begin with an overview of the main concepts in week one, then dedicate one week to each of the four stages. If you want to better understand how design systems mature in a wide variety of contexts, if you're feeling that your system has plateaued, or if you want to find a group of like-minded design system learners, this may be for you.

If you have interest in one of the cohorts being offered, or if you have an idea for another cohort topic, please inquire below about participating. The cost is $999 per person. I encourage you to attend with a peer from your team to get the most out of the experience.

My Perspective on Design Systems

The best design systems are simply a force multiplier for what’s already happening inside an organization. Those systems refactor the already established practices and patterns of the org so they can be used everywhere. If your organization has healthy practices and patterns, your design system can help scale those across teams/brands/channels/etc. If your organization has unhealthy practices, expecting a design system alone to fix those practices is misplaced optimism.

Design systems distill and magnify healthy practices and patterns while exposing and challenging unhealthy ones. The amount of resistance a healthy design system team experiences is directly related to the unhealthiness of the organization’s established ways of working. To address this, I've developed a series of mental models and frameworks based on nine years (and counting) of design system experience, five years of design system research, and hundreds of conversations with design system experts.

I can’t solve all your problems with coaching or a cohort. But together, we can discover what’s causing them and make a plan to unlock your system’s healthy maturity.


© Copyright Ben Callahan All Rights Reserved