What do caricatures, public speaking, and user experience design all have in common? I was fortunate to answer this question when I interviewed Rachel Gregorio. She’s tailored her career around her talent as an artist and passion for user centered design. In addition to being incredibly talented at the aforementioned disciplines, Rachel is kindhearted and can be trusted to handle any difficult situation with grace and professionalism. AKA, she’s the type of person any team wants around!

As a User Experience Designer at MITRE, Rachel is also a founding member of “Team Toolkit”, the group that curated a list of innovative tools for The MITRE Corporation [e.g., The Innovation Toolkit (ITK)].

Growing up in the “Disney Era”
Early on, Rachel recognized her love for art. As a young child, she started drawing her favorite Disney characters and was taking cartooning classes by age 7. For those of you wondering what is meant by “Disney Era”, all you have to do is ask anyone that remembers the releases (and classic sing-alongs) of The Little Mermaid, Aladdin, The Lion King, or Beauty and the Beast and you’ll get your answer. Rachel went from using the book How-to-Draw Mickey and Friends to starting her own caricature business when she was 11. By 16, she was drawing caricatures in Boston’s Fanueil Hall and conversing with strangers. She’s even illustrated a few children’s books! These communication skills and experiences being in front of an audience continue to help her today as she facilitates ITK workshops (more on this later!). Rachel promised to make a caricature of Team Toolkit if we can find our way into a major business or innovation magazine!

Making design part of your job
Pursuing an art degree seemed like a natural fit, but Rachel wasn’t sure this perfectly aligned with her career goals. Throughout her early career as an artist, she’d learned the importance of good communication. So, why not simply pursue two degrees? (um…because its hard?). And that is exactly what Rachel did, double majoring in Communications and Studio Art at the Boston College. Rachel started her career in marketing, as it seemed like a natural blend of her two majors. Not stopping there, Rachel went back to school for a master’s degree in Interactive Media. Some courses in UX design helped her discover an opportunity to combine her interests in design, communication, and business, and she decided that this is what she wanted to do.

Team Toolkit, enter stage left!
After starting at MITRE, Rachel found herself attending an innovation interest group organized by Dan Ward, a fellow Team Toolkit member. It wasn’t long before Rachel, Dan, and a few other soon-to-be ITK founders (Aileen Laughlin, Stephanie Medicke, and Jessica Yu) got connected with a Boston startup to provide some feedback on their products and user-centered best practices. They kept using repeatable methods, so they decided to make an Innovation Toolkit curated for MITRE. Thus, Team Toolkit was born. Rachel describes the ITK as methods that bring people together, allowing more affective meetings that enable them to achieve their goals, solving their problems together. Though the ITK is a significant part of Team Toolkit’s responsibilities, a significant amount of time is spent preparing for and facilitating “workshops”. Being front and center for what can be hours or even days is pretty normal. Rachel attributes some of her comfort in front of an audience to her involvement with Toastmasters, where she led the chapter at her first job. Not bad for someone that says they were a bit shy beforehand!

Have a Slice of Failure Cake?
When asked what some of her “best failures” have been, Rachel talked about the importance of experimenting with your career. She suggested finding roles and people that you like, searching for creativity, working it into your job, and constantly reflecting. Rachel noted that we put this to practice on Team Toolkit. We celebrate failure by learning from it. We’re lucky MITRE has been so supportive of our “intrapreneurship.”

The TEAM of Toolkit
If the reader takes anything from this article, Rachel wants it to be this: If you can find the right people that have the same passions and interests as you, you can make your job so much more than it is on paper. The challenge is finding those people; Team Toolkit is lucky to have done so.

Earlier this month I sat down with Niall White for an interview, the latest in our ongoing Meet Team Toolkit blog series. Well, I’m using the word “with” loosely, because I was in Massachusetts and he lives in Utah. We talked about music, art, cake, stinky cheese, and – of course – innovation. Niall is smart, analytical, funny, and a genuinely nice guy. Hope you enjoy the interview!

Dan: Let’s start with a get-to-know-you question: Say one word that describes you… and then say some more words about it.

Niall: One word is probably optimizer. I’m very analytical and like to be sure about things. So I’m always considering my options to make sure I’ve picked the best one. I love doing a lot of research but I also try to avoid overthinking things or spending too much time on research. Sometimes I succeed in that…

D: How did you end up at MITRE?

N: I first heard about MITRE from my dad when I was a kid. He was an Air Traffic Controller who worked with MITRE and always had good things to say about the people. Then in grad school, I interviewed with the company and got a great offer. Two years later, I’m still here!

D: What did you study in grad school?

N: I got an MS in Information Security Policy and Management, at Carnegie-Mellon, which is a fancy way of saying I studied cybersecurity. While I was there I also took a few courses in design thinking, and that’s a big part of how I got involved with the Innovation Toolkit.

D: Aside from working on ITK, what else do you do at MITRE?

N: I mostly support Public-Private Partnership and Acquisition projects, helping to translate technology into requirements and building strategies.  But the ITK work overlaps a lot with my day job – it’s fun to pull design thinking and ITK into the cyber-type work, whether it’s cyber testing or program protection.

D: What’s it like to be part of Team Toolkit?

N: It’s great! We all have so many diverse skills and backgrounds, which is really cool. As someone whose primary expertise is in the cyber realm, I can definitely empathize with people who don’t automatically feel like they are part of the design thinking crowd, or maybe feel like these methods aren’t really for them. Because of my background, I can help show that ITK is really for everyone.

D: How might you explain ITK to someone who’s not really familiar with things like design thinking or innovation?

N: I’d say these are tools that help adults be kids again. They help us tap into a more creative mental mode. These tools change our speed, exercise a different part of our brain, and ultimately make us better problem solvers.

D: Do you have a favorite tool?

N: Yeah, I really like the Premortem. And Mind Mapping. And Problem Framing. So I guess I have three favorites, but they’re all sort of related. Too often teams jump right to a solution or end up being busy for the sake of being busy. These tools help make sure we know what the problem really is, and they give us permission to have really important conversations we might not otherwise have. Conversations like “What problem are we really trying to solve?”

D: One of the things Team Toolkit does is celebrate failure with cake. Do you have a favorite flavor of Failure Cake?

N: I like failure cake that tastes OK. All too often failure does not feel OK, so I’d love it if failure cake was an OK flavor. Maybe vanilla? And let me add that if Team Toolkit was a cake, it would definitely be my favorite kind of cake: Funfetti, with all the colors and flavors together. Confetti is my favorite thing.

D: I borrowed that last question from when your wife Kaylee interviewed me, and this next question is from her too. If ITK were on the cover of a major business / innovation magazine, what would you want the cover to look like?

N: I’d want it to be an art montage by Lane Smith. He’s the illustrator who did Stinky Cheese Man, and I really like his visual style. It would be so cool to see how he would represent Team Toolkit.

D: Final question – is there anything else you want to tell the world about ITK?

N: It’s such an amazing team, and I hope more people can find themselves on teams like this. Everyone deserves this at least once in their lives!