Learning to Learn and Learning to Teach with Shelby Spees

Matty talks with Shelby Spees, a developer advocate at Honeycomb and former English teacher who has taught and tutored since high school, about learning how to learn and learning how to teach. The topic started when Shelby tweeted about a talk idea and Matty offered to record an episode. The cold open is Shelby: "I needed the 'So, what?' on Kubernetes."

Growing People Who Live in Production

Shelby says the idea grew out of a Twitter discussion the year before about what makes an SRE: is there a junior SRE, do you need an Ops background. Shelby wants more people living in production and sees observability as helping. Shelby is wary of being prescriptive, noting that many senior people cut their teeth in server rooms while newcomers have never seen a server rack, and Shelby is a cloud-native engineer who has never worked on-prem. Shelby's own lesson came from owning a tool without releasing a new version, since a year into a career Shelby didn't know how to release a Python package: pretty maintainable code is meaningless if it doesn't reach users. The question is how to teach deployment, maintenance and long-term software life cycle to bootcamp graduates and CS students.

There's No Linear Path

Matty says experience is the best teacher but "you can't do unless you have experience," and that it's hard for experienced people to shift their frame. Matty recalls a tech screen with softball opening questions that virtualization-era candidates, who never dealt with hardware, couldn't answer, and trying to learn an API at PagerDuty whose documentation was written by developers for developers, though many consumers were ops people. Matty says Gatsby is built for React developers, which is why it's frustrating for others.

Shelby says "there's no linear path to software practitioner knowledge," and with so much information, constantly changing and deprecated, you can't expect people to have the same knowledge. Even senior people benefit from building from first principles, and Shelby tries to state up front who the intended audience is and what readers should know. Matty learns best when solving a problem, like struggling to understand Habitat until finding a use case, and likes "journey tutorials" that start with the problem and not just how to call a function.

The "So What?" Question

Shelby says developer advocacy makes you want to have experienced something before talking about it, and describes a second internship outbrief that the CEO wanted to attend, which led to coaching from people who present to three-star generals on organizational impact and the question "So what?" Shelby needed the "so what" on Kubernetes and load balancers when reading the SRE book in 2017, and says product pages and open source repos often fail to say what problem they solve or why to choose them over the standard library.

Plan Your Message

Matty says communication is a skill, and that both took a structured course called Communicate to Influence. Having a plan for what you're communicating beats a brain dump, which is what podcasts are for. Shelby says that when feeling insecure about being technical enough, the instinct is to drop a stack of books on someone's desk, but "the firehose doesn't really help people learn." Shelby is a stronger writer than ad hoc speaker, and writes internal docs in half an hour in response to questions. Both admit they rarely use the method they learned, though it's effective, and Shelby's manager suggested using it for CFPs.

How to Learn

Shelby's first tip is to figure out your learning styles, which are a spectrum: visual, auditory and kinesthetic. Shelby is a multi-modal learner who needs to interact with a thing every way and takes three to four times as long to grok something, but then can teach it. The second is the book Mindset, about growth mindset. Shelby grew up very hard on themselves and thinks the industry has gotten better about the gatekeeping and incredulity toward people who haven't heard of something yet, and Matty links a talk by Sasha Rosenbaum on Mindset from a meetup the week before.

Matty ties it to psychological safety, which isn't just not being mean but includes how you answer a question in front of others. Matty recalls mocking a colleague in HipChat for a capitalized SSH flag, which sent the message that "If you make a mistake, Matt will make fun of you." You should think about the people listening, not the people you're talking to.

Shelby says early in a career, teaching PhD-level aerospace engineers a Python library showed that everybody has gaps and "there's no linear path to expert." A platform engineer at Honeycomb admitted not fully grokking something, and Shelby blogs about things like breaking DNS on a Hugo site to share those gaps, and learns by thinking out loud and tweeting. Shelby also recommends Lichtenbergianism, a book about procrastination as a creative strategy, and embracing abortive attempts, the half-finished repos and unpublished posts. When learning a codebase, Shelby refactors and renames to see ripple effects, breaks things, then clears the index and starts a new branch for the real work.

Risk and Privilege

Matty notes learning in public carries different risks for different people, but cites Annie Hedgpeth, whose blog about learning InSpec became the documentation linked from the product page. Matty, who learned by doing without a degree, credits Scott Hanselman with the observation that someone who doesn't look like Matty wouldn't have gotten the same chance to not know what they're doing, and recalls being asked about a VPN in 1998 and told to put one in the next day.

Shelby says luck mattered too: on the first day of a second internship, a product lead asked the linguist whether they wanted to write a translator, which turned out to be compiler theory. Shelby says being able to spin that into a positive story is not available to everyone, and that appearance and paper credentials lend credibility to some people. There's a disproportionate penalty for people who don't fit the mold when they raise organizational issues or push for psychological safety, and "Move fast and break things" doesn't work for everyone. Shelby thanks senior people and people outside minority groups for raising it, because it takes the burden off those more impacted and avoids being labeled as ruining everyone's fun.

Matty plugs the return of Deserted Island DevOps on April 30th, with scholarships for underrepresented speakers who lack a Nintendo Switch or Animal Crossing. Shelby will speak at Developer Week in February and join an InfoQ panel.

• Learning Stuff With Ali Spittel - ADO Episode
• Managing Your Mental Stack - ADO Episode
• Mindset: The New Psychology of Success
• Sasha Rosenbaum's talk about Mindset
• Lichtenbergianism: procrastination as a creative strategy