Rising to the design leadership challenge

As I’ve grown in my design career, I’ve come to a point where it’s becoming very obvious that I need to rise into the position of a design leader. Five or six years ago, I would express frustration at the fact that there weren’t that many good leaders in the design community and that it was difficult to find someone who I could look up to and aspire to be like. I now find myself in a spot where I feel the need to actively work towards becoming that leader.

I’ve also learned a lot about myself as a person and the type of employee I am. I’ve learned that I’m very good at working within a given set of constraints and nailing the execution of the work within those constraints. I’m quick to spot how a certain product or team functions, and I can very efficiently work within those boundaries to deliver good output. But put me in a position where I’m allowed (even encouraged) to cross those boundaries and break free, to push the vision forward and drive the team towards a new world, then I’m in trouble. I’ve learned that I’m not very good at motivating people and getting them excited about building something a certain way. I can sell my designs and ideas quite well, but forcing a mindset shift within the team I’m working with or causing a behavioral change in my users’ workflow requires an entirely different skillset that I’m not quite sure I possess just yet.

After much pondering and introspection, I’ve come to realize that a lot of this simply comes down to personality. I’m just not the type of person who shows up to work hi-five’ing everyone and getting them all jazzed up to build great user experiences. I know many designers like that, and they definitely employ the “get your teammates excited about it” strategy quite effectively. I tend to be way more rational and practical about what we’re doing and why we’re doing it, with which I inadvertently bring about some sense of caution amidst the team and a pressing need to avoid recklessness in the process. I spell out what we’re doing in plain English and I’m very honest about what I know and don’t know about the design. I will flat out say that I don’t know whether this will work, which doesn’t exactly inspire a jolt of confidence in the engineers building it. Design is a bet a lot of times and it often feels disingenuous to me if I were to stand there and claim that I know it will absolutely work. There’s just too many factors outside of our control that determines the success or failure of the product.

I had to take one of those Predictive Index tests before starting at my current role, and I didn’t think much of it. I answered the questions and gave my result nothing more than a boring glance. It was just another silly quiz that companies forced you to take as part of the interview process. Looking at it more closely now, it’s actually quite accurate. It says things like I’m a diligent worker, that I won’t “rock the boat”, that I can collaborate with others very effectively, and that I can build trust within teams quickly. It certainly fits the description of how I tend to work. I’m introverted by nature and my Myers-Brigg personality type came out to be ISTJ when I took it in high school. So I’m not shocked at all by the fact that these traits carry over to my working style.

The problem comes in that design leadership requires a very specific type of skillset. It needs you to be that person that can stand in front of a team of experienced product and tech leaders and deliver with utmost confidence a speech about why your design is going to work, all without using any numbers or data but based on gut feel and instinct alone. This is a really hard sell, especially when design can be such a subjective thing to react to. One seed of doubt in the back of someone’s head and it’s all over. You need a lot of conviction and thick skin to do this, and I fully recognize that I’m not quite there yet.

Beyond that, becoming a design leader means mentoring and coaching the more junior designers into a path that best matches their interests and skillsets. I was desperately looking for someone to coach me in this when I was starting off but never quite found it. I ended up realizing that I love prototyping, UX research, and game design simply by trying a whole bunch of design projects and realizing what felt good to repeatedly do over and over. Now, I feel very strange being put in the position where I’m expected to give a junior designer advice on what to focus on and how to advance in their career. I barely know how I ended up where I currently am, how am I supposed to tell them what to do? I keep changing my own mind about what part of design I enjoy and want to specialize in every day, how do you expect me to tell that to you? Again, this is another area where managers tend to use their own personal experiences to dole out advice to the junior designers, without giving too much of a thought as to whether or not it’s really applicable to them. I also find this somewhat disingenuous and have thus not delved into the managerial aspect of design just yet, despite opportunities having opened up in this realm.

All of this is also happening at a very interesting time in my career as a whole where I feel like I’m not quite ready to commit fully to it. I’ve always been the type of person who enjoys variety in their day to day life. I go out of my way to ensure that I’m constantly filling my day with a variety of activities. I don’t want to be doing the same thing for ten hours a day. It doesn’t matter what product you’re building, it doesn’t matter what your company mission is, it doesn’t even matter if you tell me that we’re going to Mars. I need to be doing different things throughout the day, even if it’s within design. This is why I’m always working on side projects that allow me to practice creative disciplines that I never get to in my day job, like graphite sketching or compositional photography. This is why I’m tinkering with building video game UIs for freelance contracts on the side, so that I get to play with wacky art styles and aesthetics that would never pass in a boring enterprise tech product. This is why I love playing and getting lost in immersive video game worlds that allow for experimentation and creative playstyles in a sandbox environment.

Variety is the spice of life, and you’d be shocked to learn how little that product you spent 10+ hours a day building and making actually matters in the long term. It’ll get redesigned, the tech will change, the market will change, the people will change, and your users will move on. All that will remain is what you learned from it. And it’s never fun to burnout on something that means so little. So this is why I’ve been trying to maximize the types of things I work on and spend my time doing as many things as I can. And this makes it very difficult to focus on the design leadership part, because it’s something that requires a huge chunk of your time and mental energy to do right. It’s not something that you fall into and coast through, you have to actively keep pushing the boundaries and force change to happen. Given my personality type and present desire to live a varied life, I’m not sure if this will happen anytime soon.

In the meantime, I’ve been doing and communicating these design leadership techniques in the ways I’ve found that work best for me. I’m very comfortable with expressing my thoughts in words, so I write a lot of blog posts. I tend to be better at written communication anyway, so I put out as much as I can in this format. These artifacts have helped a lot in getting my name out there and expressing myself in a crowded world of creatives that all seem to be yelling “look at how cool my work is”, whereas I’m taking the calm and silent “here’s what I’ve learned, maybe it’ll help you too” approach. I’ve got a long way to go, but for now, staying focused on keeping my wide variety of interests engaged and putting out stuff in the formats which best suit my personality and work style seem to be working out quite well so far, so I’d love to see how far I can push the design leadership envelope by continuing to do this. It’s going to buckle and break at some point, and I’ll have to adapt and change with it. But until then, I plan to keep going with what’s been working so far and keep having fun with it.