From Teacher to Tech

In April of 2023, I was offered a dream job at one of the best private high schools in the Tri-state area. It was a dean-level position, making plenty of money, and working alongside school leaders who attended the same graduate school program that I did. On paper, it was perfect. But I dreaded accepting the offer. Playing politics and climbing the administrative ladder at another private school felt exhausting, even in the abstract. So, half-terrified, I turned the offer down.

What was making me excited and energized around that time was the work I was doing leading school committees on virtual instruction and AI policy. The best part of my day was sitting with the IT department at lunch. I had discovered a passion for edtech during the pandemic and wished I could pursue it further, but I worried that I was “too much of a humanities person” to break into tech. Luckily, I was wrong.

Like many teachers looking to pivot into tech, the first few options seem obvious. Instructional design? Customer Success? etc. Eventually, I found my way to a job I never knew existed called “Conversation Designer.” These are the people who design the interactions we have with chatbots and voice user interfaces. It lies at the intersection of a few things I love: psychology, design, English, and AI training.

Before creating a plan, I spent hundreds of hours immersing myself in the space: listening to interviews with Conversation Designers, reading job listings, watching panels at conferences, and trying to figure out what constellation of skills would make me hirable.

Slowly but surely, a study plan came together, and this was my approach:

Part I — AI Foundations

1. Take AI For Everyone by Andrew Ng (Coursera)
2. Take Learn Prompting
3. Take Prompt Engineering for Developers (DeepLearning.AI)

Part I Reasoning: My thinking was that, in starting with some prompt engineering basics, I’d be better able to engage with GPT4, improving its usefulness as my tutor for the rest of my course of study. For that reason, it made sense to do this work as a kind of prerequisite. At the end of my studies, having an understanding of concepts like “role-prompting” and “chain of thought” helped me to design better chatbots for students.

Part II — UX Foundations

1. Read Microcopy by Kenneret Yifrah
2. Read UX For Beginners by Joel Marsh
3. Take UX Design Fundamentals by Joe Natoli (Udemy)

Part II Reasoning: Conversation Design is a close cousin of UX design and UX writing, so knowledge in these areas also felt foundational. Both of the books above provide a fantastic overview of UX Writing and UX Design respectively. The Natoli course had relatively little overlap with the Marsh book and was framed around the five elements of UX: Strategy, Scope, Structure, Skeleton, and Surface. If you are interested in UX Writing, Microcopy is basically a bible.

Part III — Figma and FigJam

1. The Complete Figma Course by Nima Tahami (Udemy)

Part III Reasoning: From my research, I knew that eventually, I would need the skills to build my own portfolio site and that I could do this easily with Figma and Framer. I saw too that a lot of Conversation Designers were diagraming their flows on FigJam, so it made sense to gain some familiarity with that as well. In job listings, I was seeing programs like Sketch, Miro, and Dialogflow getting mentioned a lot but people in the CxD field were talking more about Figma, FigJam, and VoiceFlow, so those are the tools I focused on. Ultimately, they‘re all pretty similar and intuitive.

Part IV — UX Writing Intensive

1. Read Strategic Writing for UX by Torrey Podmajersky
2. Read Mismatch by Kate Holmes
3. Read Content Design by Sarah Winters
4. Take UX Writing Fundamentals by UX Content Collective

Part IV Reasoning: My thinking here was that a good understanding of UX Writing would serve me well when I started studying Conversation Design. From understanding voice & tone, to localization & accessibility, it felt like this content would be good to have and would be transferable to CxD. In retrospect, I might have taken a different course because UXCC’s final project is so flawed that it’s difficult to make it work as part of a portfolio.

Part V — CxD Intensive

1. Read Conversations with Things by Diana Deibel
2. Read Designing Voice User Interfaces by Cathy Pearl
3. Take Conversation Design Certification Courses by CDI (plus Conversational Copywriting and AI Training courses)

Part V Reasoning: So these were THE two books recommended most in the field of CxD. I lost track of how many times these two titles came up in interviews, vlogs, and panels. The CDI is the gold standard in this nascent industry. Their certification actually showed up as a desired qualification in some job listings I was looking at. Generally speaking, BootCamp certifications don’t mean anything. Companies want to see your portfolio and understand the way you think about solving problems. With that said, the CDI certification felt like something the industry would broadly recognize as valuable. The CDI provided me with the documentation templates I needed for my chatbot design project. Super valuable.

Part VI — Python and NLP

1. Take Complete Python Developer 2023 by Zero to Mastery
2. Take Natural Language Processing in Python Course by Data Camp

Part VI Reasoning: A lot of conversation design job listings look for someone with experience in natural language processing. I realized that to learn NLP, I would need at least the basics of Python. Python is one of the most intuitive coding languages to learn, and with the advent of GPT4 and Copilot, learning to code has never been more accessible. Once I had the basics of Python down, I was able to apply it to specific NLP projects like transcription, sentiment analysis, and spoken language processing. This was the part of my study plan that made me the most nervous going in. Ultimately though, I wasn’t trying to become a dev. I was trying to be a valuable member of a cross-functional team that includes devs. In retrospect, I wish I had learned JavaScript because that’s the language native to the Voiceflow platform I use for my bot designs today.

Part VII — Agile

1. Take the Agile Scrum Master Certification Course by Simplilearn
2. Read Sprint by Jake Knapp

Part VII Reasoning: There were a few people I spoke with who suggested that this part of my study plan might be overkill, but instinctually, it felt important to me. I had no familiarity with Agile, never worked with a PM, and had never participated in a design sprint. I’d heard conversation designers talk about the importance of communicating with devs and PMs and getting this certification felt like a place to start. These courses get a lot of criticism because they can be expensive, and ultimately it’s your real-world experience that matters. With that said, I adored this course and ended up getting a perfect score on my certification exam.

Part VIII — Voiceflow and Portfolio Design

Learning Voiceflow and how to create impactful portfolio projects is something I had to figure out without books or courses. I found so many people willing to help online- Discord, ADPlist, etc are amazing places to connect with others and get help. However, designing my own website ended up being easy because of all the time I devoted to UX and Figma. Voiceflow was tougher at first, but once I learned some design patterns I could use over and over, it was easy to follow the CDI’s design process, write good prompts, and create a chatbot capable of teaching high school kids.

Part IX— Networking

1. Attend Voice and AI 2023 in Washington DC
2. Attend EdTech Week 2023 in New York City

Part VIII Reasoning: With a completed portfolio of projects and my LinkedIn as optimized as I can make it, the next step is to go do some networking in the real world. I love conferences. People are there to talk about themselves and about their companies, so it’s typically very easy for a newcomer to seek advice and guidance. What I heard many times is that the CxD is a small world, full of people from diverse backgrounds, eager to support one another, so I’m not nervous. Part of me does feel like a kid who has been practicing t-ball in his backyard showing up at Yankee Stadium, but everyone feels imposter syndrome when breaking into a new industry. Based on the people I’ve met so far, I’m optimistic I can count on these communities to welcome me in.