Teaching Technical Skills: When You’re Ready, How to Prepare, and What to Do When You’re Wrong
Teaching has a well-documented upside for the instructor: it reinforces your own learning and improves retention, especially when you learn with the explicit goal of later explaining the material to someone else. But the format of that teaching can vary widely, from structured workshops and conference talks to less formal venues like Twitter threads, live streams, or even open sourcing your own code. To explore the practical side of sharing technical knowledge, we gathered insights from three engineers who teach regularly in different contexts: Jerome Hardaway, senior software engineer at Microsoft and executive director of the non-profit Vets Who Code; Cassidy Williams, head of developer experience at Remote; and Anthony Sottile, staff software engineer at Sentry and a prolific open source maintainer and Twitch streamer.
Knowing When You’re Ready to Teach
All three panelists agree that readiness is less about a formal threshold of expertise and more about hands-on experience with the subject matter. Hardaway, who trains military veterans through Vets Who Code, says he won’t teach anything he hasn’t put into production where users can critique it. “I want to be confident in answering questions or correcting misconceptions or errors,” he explains. Sottile echoes that sentiment, noting he learns technologies by using them across multiple projects before he feels comfortable teaching them. “I’m not comfortable teaching until I’ve faced some adversity,” he says, referring to the stumbling blocks that students are likely to hit.
Williams offers a different calibration: you may be ready to teach sooner than you think, provided your audience knows less than you do. “A lot of times, beginner coders are good at teaching other beginners because they’re teaching from a beginner’s mindset,” she notes. The same logic applies at more senior levels—engineers are often best suited to teach peers who are close to their own skill level, which reduces the risk of accidentally assuming prior knowledge that the audience doesn’t have. For her, the real signal of readiness is being able to hold a conversation with the audience’s level of understanding in mind.
Preparing the Material
The panel’s preparation methods share a common theme: documentation. Williams is an avid note-taker, capturing everything from single thoughts to essay-length entries, which she says makes it relatively straightforward to later convert notes into slide decks for talks. Hardaway describes himself similarly, keeping dozens of notebooks to record how he learned a topic—the specific problems he faced and the metaphors that finally made a concept click. “A lot of teaching comes from documenting how you learned, then turning that into something tangible and manicured that you can share with others,” he says.
Sottile takes a slightly different approach, particularly when he’s teaching a topic where he doesn’t yet consider himself an expert. He does supplemental research before a stream or video, reading documentation and studying other people’s projects to gain broader context. The goal is to ensure that his understanding is not just deep but also wide enough to anticipate questions or edge cases that might come up during a live session.
Building Confidence and Handling Imposter Syndrome
When it comes to confidence, the panel recommends lowering the stakes and starting small. Sottile suggests giving a presentation internally at your own company or to your own team first. He also points out that live streaming is a naturally low-stakes medium: “You probably won’t start out with a large audience, so you can build confidence as you build a following.” Hardaway uses one-on-one mentoring sessions as a testing ground for new teaching strategies, since the pressure is lower than with a full class and he can adapt in real time based on the student’s responses. If something works across multiple individuals, he knows it will likely translate to a larger classroom setting.
Williams adds that it helps to pre-plan for when things go wrong, rather than dwelling on worst-case scenarios. She recommends being comfortable with saying “I don’t know that answer. I need to do more research.” She also suggests having a strategy for dealing with disagreement or outright rudeness from an audience member. “Often the best thing to do is say: ‘Please hold that thought so we can discuss afterward,’” she says, noting that taking a conversation offline can defuse a potentially argumentative situation.
When You’ve Taught Something Wrong
At some point, almost every teacher discovers that the material they’ve been teaching is outdated, incomplete, or flat-out incorrect. The panel’s responses focus on transparency and using the mistake as a learning moment. Sottile’s practice is to alert viewers that his content is outdated and produce new, corrected material as well. “Sometimes I make videos where I tell people how I used to do things and the reasons I did them that way, then explain why I changed my mind,” he says, adding that “the YouTube algorithm really seems to like ‘I screwed up’ videos.”
Hardaway treats errors as a live teaching opportunity. When he’s wrong, he works through the issue together with his students, showing them the process of diagnosing and fixing the error. “It builds trust with the student when you make mistakes and you work with them to correct the issue,” he explains. He also points out that this approach conveys an important lesson: knowledge comes from the cultivation of past mistakes and efforts, not from an inherent superiority in intelligence.
Final Advice for Aspiring Teachers
Before signing off, the panel offered several practical suggestions. Hardaway recommends building templates for your teaching materials so you’re not recreating the structure of your content from scratch every time, which frees up energy for the subject matter itself. Sottile emphasizes identifying your own learning style and teaching accordingly: he learns by doing rather than reading, so his videos are all project-based. Williams counsels against perfectionism, reminding aspiring teachers that “perfect is the enemy of good.” Her advice is straightforward: “Just start producing learning content, and the improvements will come with time.”
