Teamwork Makes the Dream Work

Thoughts on my first time being in a management position

For about the last year and a half of my time at thoughtbot, I was the Design Director of the Boston office. It was also the first time thoughtbot has had such a role. Although thoughtbot has always had great design talent, the ratio of designers to developers was low and this typically meant that only one designer is staffed to on a project and was often times working in silo. As someone whose interest in development started because I wanted—needed—to be able to build my designs from scratch to completion on my own, you could say I was also used to operating independently. However, when the new role was announced, I was glad that the desire for a tighter design team and stronger design culture was made a priority—and was honored when asked if I’d be up for it. It was my first experience being in such a role, and here are some of my takeaways from it.

It pushed me out of my comfort zone

On a personal level, I found the title of "Director" to be a motivator in getting myself out there and more involved in the larger design community of Boston. I felt like a representative of the robust design team I knew we had, and I wanted to share that. So I went to those early-morning and after-work meetups, said "Yes" to public speaking opportunities, rolled up solo to tech-related social gatherings, and cold-emailed people to ask if maybe they’d like to meet. When I was younger, I was never the one who ran up to introduce herself, and if I ever had to speak in front of a group of strangers, I would stay up all night before worried. I’m thankful for the push and confidence that this role gave me, and, in hindsight, those things that I used to attach anxiety to now seem silly.

When I first started as the Design Director, there were three designers (myself included) in an office of around 10-15 developers, so we were spread thin. We knew that in order to cultivate a more creative and collective atmosphere for design in the office, we had to start doing things for ourselves. One of the first changes was bringing back the weekly in-person design critique. At first, I felt awkward and forced about it, as if I was stealing time from people who were focused on their work. On top of that, even though the three of us had worked there for a while already, we hadn’t the opportunity to get to know each other’s work, perspective, and style. However, we were all onboard towards building the design culture we wanted and knew that critiques are always good for all involved, so it wasn’t long until our crits were excitedly collaborative affairs. This also led us to want feedback faster than just on a weekly basis, so we began frequently sending design "pull requests" amongst the team via tools like RedPen and Invision. Setting a regular time aside not only significantly improved the quality of our work, but quickly warmed us up together as a team.

I love the feeling of moving as a unit

After a few months, our Boston design team grew from three to a total of seven designers and it felt like we were on fire. We had set collective goals and we were making headway together. Our two main priorities were to expand the design reputation of thoughtbot and to make thoughtbot an even better place to work for designers. With its culture of learning and active contributions to open-source, thoughtbot has a well-deserved reputation in software development circles. As designers, we wanted thoughtbot’s design reputation to match and were confident in our capabilities. The Boston team took this on by leading the redesign of the thoughtbot site, with the vision of letting each designer’s creativity shine by giving every page personal attention. We were contributing regularly and openly with more blog posts and Dribbble shots, and hosting and attending events as a team. As a result, we were seeing more leads coming to thoughtbot specifically for design work. Internally, we were jelling too! Critiques were constructive, the general atmosphere felt more social and collaborative, and we even did artsy bonding exercises during Investment Time. Design had a louder voice within the company, we were able to staff multiple designers on one project (something we wanted for a while), and were generally encouraged to do what we think is best in whatever the situation.

Before I started working at thoughtbot, I spent almost two years as the sole designer at a startup, so for a while there, you could say I was more familiar with functioning as a one-person unit. However, once we found our rhythm and started seeing returns from the changes we were making, our seven-person unit felt like one—and I loved it.

I got to experience hiring from the other side

Being on the other side of the recruiting process was enlightening, and it was hard in a different sense. The goal is to find the "right people", but what does that mean? When it came to recruiting for design, we had multiple discussions around what we were hiring for. Were we looking for people who were strong product designers, front-end coders and consultants (e.g. sticking with what we’ve been doing), or should/could we hire designers who’s not as versed with code, for example, but would really elevate the visual quality of our products with their branding and illustration talents? Furthermore, one of the advantages of working at a consultancy is the various types of work one could be a part of, and the team was itching to try new mediums, like AR, VR, and 3D. We hoped that by attracting different skillsets, we could break into new ground and all learn something new. We’ve had some success as a company when pitching new tech capabilities to potential clients, but that’s not always the case. So we had a bit of a chicken-or-the-egg problem—how do we balance what we want as a team in the long term with what we can support in the near term?

Some other thoughts related to hiring:

  • I hadn’t really appreciated before how much time and effort is needed to proactively seek out, meet, and maybe even lure solid candidates.
  • I like sending vague rejection emails just as much as I like receiving them—that is, I don’t at all.
  • There were people who I met that I wanted to work with, but, for one reason or another, the timing wasn’t right. Still, it’s rewarding to have met them and I felt like I got to know the community a little bit more every time.

It’s about support first and foremost

The alliteration is nice, but "Design Director" seems like a misnomer for what the role was—at least for me. As I got more settled into the role, I found the term "team mom" to be more apt. The best way forward in probably every situation is when everyone involved is invested, self-motivated, and happy with what they’re doing. And people already knew what they wanted next—from the artistic and tech skills they want to improve on, to specifically what type of apps for what audience they’d like to make! I was fortunate to work with some of the most pro-active and self-reflective people I know.

I found that, in practice, the biggest impact I could have sometimes is just helping make the connections. It was keeping an eye out for any opportunities people have expressed interest in and plugging the two together. Like this one time, a designer had mentioned that he’d like to give his first talk somewhere, and it so happened that I had just been chatting with an event coordinator about doing a meetup together. Kismet! Other times, it was going to and evaluating sales meetings to scope out potential projects and see how they might best fit the skillsets our designers have asked to work in. Whenever this happened, it was a win-win for everyone—people were bettering themselves while building the portfolio and reputation we wanted as a team.

But most of the time, being "mom" meant just moving aside and making sure designers had the space and support to try things. And our designers had great ideas! We did office-wide arts and craft on Fridays, made a dedicated (and active) design critique Slack channel, held inter-office design competitions, connected with other design firms in the area, altered how design sprints were ran as a process within the company, sponsored and hosted events—to name some of the things we explored all because each designer had their own spark about how the team could improve together. In these cases, sometimes the most I had to do was just let them know that yes, that’s a fantastic idea, the company is behind them on it, and repeat the thoughtbot motto: "Use your best judgement."

I never actually directed people on what to do—I never needed to and wouldn’t dare anyway, they already knew! The biggest reward I got from this position, I think, was that I got to know people by learning about what want from their careers. Having the chance to do what I could to encourage them forward was icing on the cake.