The Dreamer, The Realist, The Critic

A few months ago at the Leading Design Conference, I heard Margaret Lee give a talk on being a Reluctant Leader. Many, many, things from her talk resonated deeply with me. Most salient was when she spoke about Walt Disney’s Creative Strategy to lead as a triumvirate that includes The Dreamer, The Realist, and The Critic. It resonated mostly because I was able to directly connect that to one of the best partnership models I have had in my professional career to date. Although less than a year, the working collaboration between John Maeda (the Dreamer), myself (The Realist), and Alexis Lloyd (The Critic) at Automattic Design was just that. Through our natural styles, all ideas, plans, and actions were hashed out, thought through, and ahead of being either too reactive or not proactive enough.

Leading in Design is challenging. Leading in Design through change is ironically that much more so, as the foundation of Design is traditionally steeped in process and iteration. But no matter how you cut it, change is hard. Being led by a visionary, The Dreamer pushes the boundaries towards ideas outside of your purview. Signing on as a Realist often means you need to believe in that vision in order to find a way to make it a reality. Getting buy-in from all levels of an organization on that vision is much harder when they don’t have a clear line of sight into that future. As a DesignOps lead, my baseline mode of operation is to translate the Dreamer’s vision into a plan that can be executed. When establishing a DesignOps practice, keeping your eyes set on the executable plan is necessary, as the daily triage is a big part of beginning to understand the pain points and develop a plan for stabilization. However, too much time spent in triage purely focused on execution is not strategic. It is this balance of execution and strategy that will keep your work (and team) grounded. Without a roadmap that connects back to the overarching vision for the Design organization, your team won’t be able to have a clear understanding of where you intend to take them.

Two pieces most design organizations have buy-in on is first a leader (The Dreamer), and then someone to help operationalize (The Realist). What became clear to me through this working partnership was the fundamental need for The Critic. The Critic consistently asks, “what problem are we trying to solve and why?” as a way to help balance between dreams and tactics. In this piece, I wrote about the value of partnership as a yin-yang balance. How in these partnerships, we gain velocity towards a common goal. What I learned is that it’s not just the right balance of two or three people, but the balance of the kinds of roles those people play in partnering. The trust and respect they instill in one another to play that role, challenging assumptions, and the openness to being wrong. 

Our usual MO is to listen to fix or listen to win. In the former, we are being efficient — diagnosing a situation to quickly solve a problem. In the latter, we may be set in getting our way, convinced of our rationale and rectitude. In listening to learn, however, we remain open and curious, setting aside preconceived notions and assumptions to gain new perspectives. – Margaret Lee

Design often becomes a victim of its success, forgetting the fundamentals of what it means to practice Human-Centered Design. Those examples in practice are set from the top. From the shape the leadership team takes, to the form, to the day-to-day. We can (and should) continue to influence that, but also need to influence healthy behaviors in relationship patterns to remain human-centered in how we lead, change, and grow.

Published by sntdo

sntdo is short for Sentido, Spanish for "Sense." All things sense-making / New Yorker born and raised / kid wrangler / Head of Design Operations @Automattic / @frogdesign @hotstudio alumn / Design Diplomat / Hostage Negotiator / Boricua