From Hobbits to bots—lessons from Simon Mitchell-Wolf’s journey to CxD

Simon Mitchell-Wolf fell in love with linguistics when he was just a kid reading fantasy novels. Something about the languages authors like J.R.R. Tolkien created for their characters captured his imagination and wouldn’t let go. 

Much like one of Tolkien’s Hobbit protagonists, Simon has since been on a great journey—one that started in the pages of a book but eventually led him to his current real-world role as a conversational experience designer at PayPal. 

After dedicating years of his life to studying linguistics, Simon’s initial forays into the world of technology left him feeling a little out of his element, not unlike Bilbo Baggins when he was conscripted to join Gandalf’s brawling band of dwarves for the journey to Smaug’s mountain. 

Happily, like Bilbo, Simon found a way to shine by bringing his unique set of talents and perspective to bear. Bilbo used his innate stealth and understanding of “human” nature to become the party’s MVP burglar. Simon used his linguistics background to look at digitally mediated communication in a very different way that focuses less on the technology involved, and more on using words to bring people together and build authentic connections and communities.

In my recent conversation with Simon, he shared some of his story along with some tips and inspiration for anyone looking to make their own way into the conversation design arena. There may not be a single clear path to a career in this space, but people like Simon are forging their own way ahead and building roles that are perfectly suited to their particular skills and passions.

Follow your passion

After discovering his passion through exposure to constructed languages in fantasy novels, Simon was already on his path. By the time he was in middle school, he knew he wanted to study linguistics seriously. And, unlike most middle schoolers’ aspirations, the dream stuck. 

He taught some peer-to-peer linguistics in high school, did some related research at boarding school, and continued his studies in college where he ultimately received an accelerated master’s degree. 

He wrote his thesis on mediated language. His paper, OMG BREAK A LEGGG LOL: Digital Discourse-Pragmatic Variation In A Theater-Based Community Of Practice, analyzes the function of three digital language phenomena (LOL, OMG, and typographic lengthening) to demonstrate the importance of digital language and discourse for building ties in within a community of student artists working together in a theater group.

Even though his specific interests and sub-disciplines shifted over the years, Simon was all in from day one and never let anyone or anything derail his passion.

Be like Simon: Believe in what you love, and give it your all. Even if your passion seems irrational or a little unrealistic. Even if you’re not sure how it will translate in real life, stick with what gets you really excited. You never know where your interests might take you.

Think outside the [career path] box 

Simon Mitchell-Wolf

With a master’s degree in hand, Simon’s most obvious path forward was to go into teaching or research. But he didn’t want to go that route. 

“I realized I didn’t want to go into academia, and I wasn’t that excited about the research,” Simon explained. “The idea of getting a PhD and a research degree, and then going into the tenure job market—which is like doing a PhD all over again—just didn’t seem like a sustainable plan.”

Floundering a little, Simon shifted gears and did some work in arts management and theater production. His was a common story. Many folks with social science degrees struggle when they try to transition into industry roles. “It seems like nothing really fits,” Simon said. “You always feel like you’re having to justify your experience and explain why your skills are relevant to the job.” 

It was all a little discouraging and exhausting, but there were better things just around the corner.

Be like Simon: Don’t assume that the only path forward is the one right in front of you. Traditional career strategies don’t always work in emerging fields. Also, it’s okay to feel a little lost—that’s often a normal part of the process. Don’t give up. 

Build a bot

Before we get to how Simon initially broke into the industry, we want to share a piece of advice that he wishes he’d been given back when he was just starting out: build a bot.

“One thing I wish is that I’d given myself the opportunity to start building my own bots early on,” Simon said. “Just thinking about how to accomplish tasks, answer questions, and communicate information would have given me a really great jumpstart.”

Simon stressed that your initial bots don’t have to be anything fancy. In fact, they don’t even need to be built with technology—you can just draft them out on paper. The main thing is to train yourself to think in terms of user-oriented design. 

Write it down. Read it out loud. And talk to people about it. For example, Simon and his wife take turns standing in for bots and users to work through how a conversation should be designed to deliver the most natural and comfortable experience. 

Be like Simon: Start before you think you’re ready. Don’t assume you have to know everything or have massive technical know-how to start testing your theories and honing your skills. Just go for it.

Dip your toes in with freelance

Simon’s first formal foray into conversation design-related career territory came in the form of some freelance conversational AI consulting gigs. The work was mostly text-to-speech projects, which were an obvious fit because of his background in phonetics, phonology, and acoustic analysis.

Simon said, “I got my foot in the door with some short-term, sporadic contracts, which got some tech on my resume.”

Eventually, he got on the radar of a recruiter who was working with Google. That connection landed Simon a shot at a “dialogue design” job with the search giant. “I had no idea what ‘dialogue design’ was, but it sounded interesting,” Simon recalled. “And once I started talking with the recruiter, I realized that I was very qualified for the job.”

Initially, Simon’s role at Google was primarily analyzing transcripts and doing a lot of maintenance and improvement. He was developing labeling techniques and ways to look at user data and metrics. “I was kind of flying by the seat of my pants,” he said. It wasn’t until near the end of his contract that he was given any opportunities to do actual design work. 

Be like Simon: Stay open to opportunities. Even if a gig isn’t what you think you’re looking for, every experience helps you get to the next experience. 

Push past your fear to find your place

When Simon came across the opportunity at PayPal, he had mixed feelings. “It was super exciting, but also super scary,” he recalled. “It was starting a new team pretty much from scratch, fully internal, at a huge company.” 

What he found, once he overcame his fears and decided to go for it, was that moving to PayPal helped him feel more comfortable engaging with the industry overall. “I started feeling like part of a community at PayPal because we had a real team,” he said. “We were a team of conversation designers who were on the same level with all these other teams.”

Today, Simon’s role is focused on actual conversation design—figuring out processes, defining best practices, assembling great documentation, and really starting a CxD practice from the ground up. It’s the kind of work he set out to do, and now he’s doing it with a great team at a prestigious company.

Be like Simon: Have faith in yourself, and don’t assume that everyone else knows more than you. Conversation design is a new area of expertise. It’s easy to doubt yourself, but the truth is everyone is trying to figure things out. The people who get in there now—even if they aren’t sure about everything—are the ones who will become leaders in the field as it matures.

Bring a new perspective

The tech industry revolves around development. Everything is driven and shaped by developer work styles and priorities. But just because that’s the primary focus today doesn’t mean there isn’t room for other ways of doing things. 

Simon brought not only his technical linguistic skills to the table, but also what he calls a “human focus,” which he’s found is often missing in tech environments. Simon explained, “I felt like what I could bring to this world was the ability to use my technical knowledge and expertise in service to user advocacy, human advocacy.”

Whatever angle you take, ensure that conversation design has a seat at the table. “One of the struggles we face as conversation designers is about how we create space for ourselves within the tech environment and empower ourselves to push back on some of the old patterns,” Simon said.

He found it helpful to look to the history of user experience (UX) for examples of how to do this well. UX professionals faced a similar uphill battle to carve out their territory and integrate with other teams, and today they're a critical part of any tech team.

Be like Simon: Know what you bring to the table, and help others understand that value. Conversation design is new to everyone, and to people not already steeped in it, it can be both confusing and daunting. Find creative ways to educate and collaborate with your peers so that they become supporters and allies. 

Be a part of the community

Throughout his journey, Simon has always sought to learn from others, whether they are people on his immediate team, collaborators, or industry peers. “I’m learning a lot from other people in the industry like Tara Nair Shah and Gina Riley,” he said. “These are people who have already positioned themselves in the industry, have seniority, and are advocating for not only users, but also for their teams.”

Simon is learning from these folks not only about the practice itself, but also about how to create space for CxD. “When we have really great leadership in the conversation design space, it helps us create space and hold our ground,” he said. “It helps empower us in the tough conversations about prioritizing, timing, and resource management.”

In addition to engaging with specific individuals, Simon also recommends getting out there into the larger CxD community. He’s not a fan of networking, but he has found that connecting with fellow CxD folks never feels like traditional networking. “CxD is still a pretty small world, and the people in it are always excited to talk about conversation design,” he said. “It’s not too late to make friends and get established.”

And don’t forget that you bring a lot to the exchange as well. Talking with your peers isn’t only about learning from them. You have experiences and insights to share as well. It’s a two-way street. 

Be like Simon: Step outside your comfort zone, and find your people. They are out there—and they’re just as passionate and excited as you are. 

This is an exciting time in conversation design. What are you waiting for?

At the end of the day, Simon feels like his journey from academic interest to practical application has been a really natural progression. “I’ve always been so interested in how language, context, and medium affects how we interact,” he said. “And these topics are even more relevant today because more and more we are interacting with machines mediated by whatever technology is between people. What’s happening now is really starting to push the boundaries of linguistics into overall communication studies.” 

Simon’s last and most generous piece of advice for anyone interested in pursuing a career in conversation design is to reach out to him. He continues to be just as passionate about linguistics as he was back in middle school when he was geeking out about the fantasy languages of elves and dwarves. 

And now he’s also excited about conversation design—where it is today, and where it’s going tomorrow. He’d love to help more like-minded folks get a jump on shaping the future of the industry.

Header image by Midjourney.


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