What I Learned From Two Years as a Design Leader

What I Learned From Two Years as a Design Leader Cover Art

by John Choura / September 12, 2020/ 11 Minute Read

As my time was ending at Happy Money, where I spent the last five years of my career, I began reflecting on the lessons I learned as a first time design leader.

In my five years, I worked with amazing people. The first three years of my tenure was as a design contributor and lead, and in 2018 I was promoted to Design Director of brand and product design. This was my first role ever running a team, managing people, recruiting for fast growth, and on top of all that maintaining a well strategized design operation for the business.

I learned a lot in those two years.

A few things came natural; my desire and ability to create a thriving culture of diverse designers, a strategy for growing the org, and my deep and overflowing passion for design and creative. However, the list of challenges far outsizes all, which includes but is not limited to: team interpersonal conflict, company vision changes, attrition, leadership alignment, struggling to detach myself as a contributor, aligning brand and product design disciplines, creating and maintaining a coherent strategy, having to fire people, and adapting to being distributed during a pandemic; the list goes on.

As time has went on, so much has become abundantly clear to me on how a designer needs to lead. To be honest, many of my realizations are painfully simple, it's merely been the direct experience that has helped me truly realize them.

Out of my reflection I wrote about seven different lessons. They don't make a comprehensive list of all the things a design leader should know, but they're the most personally impactful lessons I can think of. I wrote all of them in a voice that speaks of my personal experience and is directed to any past, present, or future design leader. Here's what I've got.

1. Release your grip

When I became the leader, my sense of responsibility spiked. This covered all aspects of the team, and was something I saw as a strength. I treated the team like it was my own little company within the company. It made me want to be a design visionary, to make changes to process, to institute new team traditions, and more. Albeit, at the start the team was only myself and 1 other designer. Which meant that while I was this new aspirational visionary, I was still directly contributing. Later, when I grew the team to 5+ designers other than myself, I was still behaving like a part-time contributor. Sometimes coach and sometimes player, at my own whim.

While this tendency came from a place of positive responsibility, as an extension of my design abilities, it translated to the team as infuriating and disempowering. Thanks to a patient team, candid feedback from my team members, and some self awareness, was I able to see the negative impact that I was making. I was taking away from them what I so clearly entrusted them with, by bringing them into the team in the first place.

A good example (yet painful to recount) of when this happened, is when I was preparing to speak for a mini all-hands where I was unveiling the new brand to the company. At this point, I had 3 brand designers on the team, each with time to spend to help me put together collateral and materials for the event and presentation. Instead, I did it all myself. Where I had recruited them, it was only for some small aspects, most of which I later took and made changes to, before the final unveiling (insert cringe ... hindsight is 20/20). In the moment, I was acting out of that deep sense of care and responsibility for the thing we were unveiling. But, I was not thinking or acting like a leader; I was thinking and acting like a designer. I felt great delivering the keynote, but afterwards, I realized that I had bulldozed my team.

Step one for me was to release my grip. Which doesn't mean that should throw out my responsibility or anything I care deeply for, but it instead means that I need to trust my people. By me releasing, it makes room for others to show their strengths, and even learn their own lessons through their own mistakes.

This act of releasing my grip was a repeated struggle, something I had to be very conscious of. I had patterns that I had built over years and years as a design contributor. Because of this, I would often try to seek comfort in those old ways and unconsciously slide back.

Great leaders aren't white-knuckling their teams into success, they're standing there with open hands letting their team do what they do best.

2. Give designers ownership

This one has always been obvious for me, but my perspective changed when I became the leader of a team. I can remember as a young designer, pining for ownership and trust from my creative director or manager. Whenever I discovered that gift of ownership (sometimes by permission, sometimes by my own mindset), I could really sink my teeth into a project. As designers, we're opinionated and bull-headed. We became creators and shapers of experiences because deep down we have an audacious belief that we as individuals can make things better. Often critical of ourselves and the world we experience, we constantly think "that could be better," to everything we see. We want to own our own ideas.

So as the new design leader, it was natural for me to believe that I (now) was the owner of everything. While that is somewhat true, since I was the ultimately accountable individual, it's a perspective that is really disempowering to each individual designer. And believe me, even if you don't utter it, they will feel it. The answer is simple, grant your designers clear ownership (or what I named "drivership") over areas of the experience. Set clear expectations, but hand over the keys. Over time, you will be able to tell that the designer feels a sense of ownership when you can see them take on a self given sense of responsibility.

3. Know your role and how you bring value

A misconception of these first two points (releasing your grip and giving ownership) is that you're totally hands off, out of the loop, and doing nothing at all. This is untrue. Your craft becomes the art of setting up expectations, leading work from a strategic level, and guiding your team members through their challenges.

When leading through guidance, it's best to let your team members discover their own conclusions. Telling them what you would do is very tempting, because you've likely been in their situation. Instead ask an open-ended question, like "what do you think should be done at this point?" This will keep the keys firmly in the hands of the driver (not you), which is the ultimate tool of empowerment. This doesn't mean that advice or "telling" is out of the question, but I personally challenged myself to balance the ask-to-tell ratio in favor of "asking."

It may look different depending on team size or level within the design org, but the point is simple; know the role your team needs of you, this is your north star.

4. Promote your people

I had the greatest privilege of being able to hire and grow a team. This meant that, at first, I was the only manager in the design org; which grew into an untenable span of control very quickly, especially as a first time manager. At first by necessity, I had to raise people up on the team into manager roles to mitigate the challenge of my manager-to-direct-report ratio.

Two really simple distinctions at the get-go here, 1) not everyone needs to become a manager and 2) becoming a manager is not the only track for leveling up within a team.

That said, there will be people on your team (as there were on mine) that will be a perfect fit for the bill of rising up into managers of people. Sometimes there wont be, and it'll be an opportunity to bring in a manager from the outside. In my time as Design Director, I was able to promote four well deserving team members to the role of manager. Additionally, in my time, I was able level up a few other folks to new individual contributor levels. Let me tell you, there is so much satisfaction in sitting down someone on the team to level them up and giving them a raise, along with a new well-deserving role and charter. That might have been the best part of the job.

5. Managing friends is hard

Before I took the promotion to become the manager of the design team, I was good friends with the two guys who were my peers. When I became their manager our friendship dynamic changed. I was now meeting with them to talk about career growth and performance; and I was now responsible for their output to the business. If you can guess, this made things challenging. I felt awkward because I didn't feel like it was easy to be a friend and a manager at the same time. Since the majority of our interactions were work based, it was hard to jump between wearing both hats. When I look back, I completely empathize for the situation there were in; it was uncomfortable.

There however was a difference for new team members that joined, they got to know me first as manager, which made things far easier. The best thing that I did with those who knew me before, was to just level with them about how weird it was, and try to be as human as possible. I even had dinner with one friend, where we vowed to not at all talk about work at all, and it was a great step forward.

No grand lesson here, just a cautionary anecdote (thanks for being awesome David and Scott).

6. Everyone is different

Yeah, no duh. This is an obvious one, but it's something to highlight when it comes to managing. There is an old-held misconception that contributors or direct reports on a team need to adapt their behavior to match up with their managers. This comes from a bygone era of a "get on my level," Don Draper-eqsue way of leadership. It's bullshit. Leaders are ultimately servants of their people, and need to adapt their style of leadership to meet each individual. There is a good model of this that I really like called Situational Leadership, where the leader/manager changes their approach situationally from directing, to coaching, to supporting, and ultimately to delegating. It's worth looking into, as there is tons of literature on the subject.

The more important lesson for me was one of humility. It takes self awareness and preparation to come into a one-on-one with a team member and meet them as individuals. I'm still very much so a student of this task, and still learning how to practice it as a leader and a peer.

7. Get a coach

Just over one year into being a design leader, I was feeling wayward and in need of guidance. Since I was the top design leader in my organization, I didn't have anyone with design leadership experience to lead and guide me through the challenges I was facing. That's when I came across the Design Dept., they're a women-led design leadership community that offers coaching and workshops. I instantly sent out an inquiry about coaching, and not to long after I was paired with my coach, and haven't looked back since.

My coach has been instrumental in helping me navigate the challenges of being a design leader. In fact, much of the reflection contained in these lessons is directly from conversations her and I have had.

Having a design leadership mentor and a coach is crucial to circumnavigating the challenges of leading a team of designers. Having someone who can speak from deep experience about the things you're actively working through is a must. Leadership positions can be lonely, and it's not always best to confide in your direct reports about the toughest challenges. While there is a cost associated with this type of coaching, any organization that cares about the professional development of their leaders will make the investment.

Well, what do you know. That's all I've got.

I'm so insanely indebted to everyone who helped make my experience as a leader a thoughtful and fruitful one. Thanks to my design leadership coach April Neufeld, I'm grateful for everything your insight and perspective brings to me. Shout out to my former manager and CPO of Happy Money, Adam Zarlengo, thanks for your support and trust in my ability to lead. I also would not have learned the lessons that I did, if not for my former team. Shout out to David Garvin, Scott Branch, Sally Alvarado, Sar Issagholian, Kathy Speer, Jonathan Wagoner, Sarah Ohye, Mark Hsieh, Kristine White, Joey Belardi, Jeff Weimer, Laura Zinssmeister, and Cat Freeman. Thanks for bearing with me, as I was figuring out my shit.