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My Biggest Regret as a Design Leader
And the three lessons I’ve taken with me.

"You're your own worst enemy."
I heard this phrase throughout my childhood and adolescence from family, friends, and educators. Each time I listened to the words, I thought I understood, but I didn't. I fully believed I was to blame for not being better at everything I tried, especially sports. The "me" that was my enemy was the me that lacked the innate physical prowess and aptitude to be the next Eric Davis, Joe Montana, or Michael Jordan. Years later, in the aftermath of my first diagnosed panic attack in college, I realized that the enemy in me was my perfectionism and impatience. That's what everyone in my life had meant when I was growing up, and it took a graduate-level economics course I thought I was failing to drive the connection. I ended up with an A and a prescription for anxiety medication.
How does this apply to design leadership?
The high standards I set for myself, and the subsequent impatience when I miss those standards, directly affect my leadership style. I must consistently be reminded to not push myself or those around me too hard. Yes, set standards and expect greatness, but meet failure with grace, understanding, and the knowledge that the work will always be there tomorrow.
It hasn't always been this way.
I found myself amid a rapid organizational transformation in a prior leadership role, with user experience and product design at the center. It was a spectacular opportunity to lead an amazingly talented team to help set the stage for the future of a large organization. We were going to do things "right" this time with our seats finally at the proverbial table we all talk so much about.
For the year leading into the transformation, I had carefully re-built my team to meet the great opportunity ahead. I interviewed many candidates, turned down most, and finally hand-picked the best designers I could find while helping coach and upskill those I had inherited. The team was energized, ready to run through walls as we set off to completely re-think what was possible and moved into a new formation alongside our product teams. Most of the team performed to expectations, but some lagged behind, leading to my greatest regret as a leader: the institution of the "Penalty Box."
Thinking inside the box.
I'm not sure who called it the "Penalty Box" first, but it stuck, and it's not hard to see why. Essentially, when a designer failed to show up as a leader within the product area they were assigned to support — at least from my admittedly skewed perspective at the time — I moved them to another, lower-priority product area to improve. This was a morale and confidence killer, but at the time, I saw it as necessary. The designer in the "box" would work hard to improve in the needed areas to get back to a more impactful assignment, or so was my logic.
Sometimes, the relationship between an employee and employer doesn't work out. And that's okay, especially if both conclude that something healthier can be planned in terms of a transition. That would sometimes happen with individuals who went into the box. They were assigned less impactful work while looking for the next opportunity, sometimes with my help. Other times, I inadvertently moved high-potential designers into the box and misjudged the adverse effects of such a move. Once I realized the mistake, it was often too late. I had irreparably damaged the relationship and destroyed any hope of regaining the individual's trust, let alone engagement with the work itself. The worst part: my impossible standards had hurt the individual's self-confidence, undoubtedly contributing to a more stressful life at home and outside of work for them—my actual greatest regret.
The Penalty Box approach is something I've long parted with, and I've had years to reflect on the many mistakes made to avoid making them again. Here are three lessons I've learned along the way:
1) The "80/20 rule" of people leadership is nuanced.
Early in my career, a mentor brought me a different take on the 80/20 principle, specifically: spend 80% of your time with the high performers on your team and 20% with the low performers. I understand the spirit of the rule: Don't waste too much energy on those lagging behind. Instead, focus on those trending upwards to maximize impact at scale. Looking back, I lumped many of those performing below standards together and applied the same strategy to all without considering individual situations or contexts. Sometimes a leader should spend much more than 20% of their time with those who need a little understanding and support to break through.
2) Mindset matters.
I was introduced to the concept of "growth" and "fixed" mindsets through Dr. Carol Dweck's excellent book, Mindset: New Psychology of Success. The perspective it afforded, specifically that each of us has either a growth or fixed view of our own development, significantly altered my approach to people leadership. Someone with a growth mindset is coachable, curious, and knows they have room to learn and grow. Their ceiling can be nearly limitless given the right environmental factors and support. If they, instead, have a fixed mindset, meaning they believe they're at a point of mastery over their skills and behaviors and can no longer improve, it's unlikely they will find long-term success. Thinking back, I had penalty-boxed at least one designer with a strong growth mindset. Had I understood it at the time, I would have taken a different approach to support and mentorship.
3) Embrace individual interests and skillsets, even if they don't match expectations.
Given the complexity of user experience and product design roles, as I've written about previously, it can be challenging to recognize and celebrate designers' strengths when they don't fit an organization's product designer "mold." I've admittedly fallen into this trap more than once.
For example, core "product designer" skills often fall across a set of interrelated skills: user research, interaction design, systems thinking, and a level of business acumen. When a product designer doesn't perfectly fit the mold as understood, they might fail to meet expectations. In reality, the designer often has passion and interests elsewhere that could benefit the company and enrich the designer’s work experience in other ways. These designers would've been prime candidates for the penalty box in my previous life. Today, I do my best to find opportunities that best fit the individual's interests and strengths. I've worked with several product designers who are now leaders in UI design, research, accessibility, and design operations disciplines — all scaling their impact further than what the standard "product designer" role would've afforded.
These are just a few of many more lessons I’m certain to learn in my career. While I still hold high standards for myself and others, I believe I’m slower to judgement and more proactive in understanding individual contexts and needs so I can be a better mentor and coach. As long as I maintain a growth mindset, I can only get better through learning from those around me.