Rands Leadership AMA

Kyle Coberly
13 min readDec 29, 2018


These are the questions I was asked and the answers I gave during my 2018 AMA on the Rands Leadership slack. Thanks to everyone who participated, I had a great time!

What’s your favorite mistake?

When I was 19, I drove from Seattle to LA and back over a weekend to tell a girl I liked her. This was a terrible idea, and (shocker) it didn’t work out well. I met someone else on that trip though, and we’ve been together for 15 years and have two children!

Hi Kyle! What’s the last thing that changed your mind and why?

My in-laws wanted to take my kids to Great Wolf Lodge, and I thought that was a little much. I gave up when I needed that emotional energy for something else. I still think the trip is a bit much, but I don’t think it’s worth going to the mat over to make a point or whatever anymore.

What’s for lunch?

I’ve been on a diet for the last 3 weeks that’s mainly centered around not going to restaurants. I have the same thing every day, and it’s been going pretty well so far. Today (and every week day), I have a ham/turkey/cheese sandwich, a “Cobe salad” (spinach, snap peas, carrots, grapes, almonds), a string cheese, and celery + hummus. If I get all of that in before about 1pm, I find that the rest of my day goes a lot better, but I don’t like eating in the morning, so it’s a challenge.

How has your experience, at Galvanize or otherwise, influenced your opinions on our primary education systems and how we may better serve our children? (My time at Udacity gave me a lot of opinions on this. Bonus: I tried to poach your instructors to come join me as much as possible — they were all amazing).

Primary education (and especially ECE) has extremely high leverage on everything else that happens in your life, in ways that are often extremely unfair since it’s when students have the least agency.

I don’t have a lot of hope for this happening, but these are the biggest changes I would like to see in K-12:

  • Switching from fixed time to fixed mastery. No grade levels, no fixed progression, no stigmas.
  • Better socialization between children of different ages. Mixing older kids and younger kids can bring out the best in both of them. Stacking a bunch of kids who are the same age reinforces the worst attributes of the age group.
  • Build better teaching teams. 1 teacher for 25 students is brittle in a way that 3 teachers for 75 students isn’t. This addresses one of the worst ergonomics issues in teaching- you don’t have people to cover for you, bounce ideas off of, share the experience with, or any of the synergies that make good teams work.
  • Rethink “subjects.” The distinctions between a lot of academic disciplines are ultimately arbitrary, and ghettoize the truth. Why would you learn statistics separately from genetics? Politics and geography are tightly related. Literature is inseparable from the time and place it was written. There’s one truth that all of these things are illuminating, and they’re much richer together. I blame our cultural obsession with tidy categories.

Educator for what audience/demographic?

I’ve taught 7th grade band, boy scout camp, ballroom dance for adults, guitar/bass/piano/drums for all ages, and software education for adults. Broadly speaking, I prefer working in transformative adult education for a couple of reasons:

  • It’s really poorly served. ECE and K-12 are generally more important and impactful, and thus get a ton of focus, but most higher ed and adult training stuff is a joke. I think people who made mistakes or just want a chance to do something new deserve great education too.
  • It’s the wild-west, both from a regulatory and culture standpoint. Many problems in K-12 and higher ed are (unintentionally) structurally kept in place. They have to work within byzantine accreditation rules, poor teacher evaluation rules, arbitrary categorization of subjects, union contracts, the weird complex of career/research/academia/resort ammenities/sports farm leagues of the modern university. Even when change happens, it happens crazy slow. In the rest of adult ed, you have a lot more freedom to apply best practices, experiment with stuff, and be creative.
  • Adults choose to be there, and often put a lot of skin in the game to do so. I don’t think anything I do as an educator is nearly as effective if someone doesn’t have the choice to walk out. Students often ask me stuff like “Do I have to do this?” and I like being able to say “Of course not- you only have to do it if you want to stay in my program, which is entirely optional.”

Do you have any ideas/tips/musings on how to engage with less-than-enthusiastic students, esp. to try and get them to the point of driving their own education?

Some thoughts:

  • I think they have to have the choice to walk away for their choice to own their education to have much meaning. That said, even in compulsory education, you can say “You have to be here, but it’s your choice whether you get anything worthwhile out of it or not.”
  • A sense of tribe and inclusion are powerful forces, and people will do more to stave off excommunication than they will to stave off failure. In free classes, I’ve recommended making the price of admission participation- you don’t do the work, you don’t get to show up.
  • Ideally you can tie the education to some current goal they have. In K-12, I think this usually comes out as “It will help you get a job some day!”, which is so far away and abstract that it’s a pretty tough to connect with that. With adult programs, you can tie it to an imminent career search (even better if it’s a current career).
  • Ultimately, I think a student has to be able to demonstrate something they think is awesome they couldn’t do before for the “oh, learning is awesome” bug to kick in. It’s easier to do with software and music (which is why I liked teaching them so much), but you can create stories, visual art, businesses, teams, and all kinds that offer the opportunity for personal expression.

Favorite Beer?

Yellow Fever by Comrade. It’s the Yellow Card blonde ale infused with jalapenos. It’s spicy enough to make your mouth tingle, and I love it with my life.

Worst management decision you’ve made?

Worst decision ever is a tall bar, but here are some that come to mind:

  • In first management job long ago (Guitar Center), I was a super-stickler for the rules. My first couple weeks on the job, I wrote people up for everything. It didn’t get me compliance or respect, it just made me a joke.
  • I tried to get some music teachers to get into commissioned sales for instruments, books, etc. I was coming from a sales culture, and I thought they would get energized by it. They took it as a huge insult to their integrity. I’ve never done spiffs, commissions, or otherwise tried to motivate employees with money ever since.
  • Recently, I ran a really collaborative team. I made decisions, but there was basically nothing we did where the team didn’t have a pretty powerful voice. We were understaffed, and I had a limited window where I thought I might be able to push a hire through, so I took it. I don’t think anyone disagreed with my choice, but the team was really hurt that I didn’t consult them. If I could do it again, I would have moved slower, even if it meant missing the window of opportunity. Trust is your most precious asset as a manager, and that wasn’t worth the price I paid.

Worst management experience you’ve been put through (by a manager above you)?

Much easier: Someone trying to shrink my team through attrition by making our work increasingly unbearable. My team kept asking me when help was coming and why we were being treated this way. I didn’t know either, and no one would give me an honest answer. I felt like we were doing everything right; we were innovative and made lots of money, and I’m not sure why that wasn’t enough. I kicked myself for a while for not being able to come up with a way to politick out of the situation- “If I only I had been more compliant / diplomatic / threatening / clever / conciliatory / gregarious, I could have saved the team.” In retrospect, I played an unwinnable game the best I could.

Who was someone you’ve worked with that was delightful? What made them so?

Your new employee, Kim Schlesinger. I’d never shared leadership of a team before I worked with Kim, and it was a singular experience. Our skillsets were both overlapping (we’re both educators who became developers) and complementary (she’s a stronger educator, I’m a stronger developer), and we shared the same leadership philosophy and sense of purpose.

The thing that was delightful is it freed me up to be more experimental and wild because I trusted her to pull me back if I got too far off the reservation. When I was feeling overwhelmed by a decision, she could sanity-check me and encourage me to keep going. I felt fine taking time off, or delegating, or not having everything completely accounted for myself. I think the team loved it because we offered them such different, complimentary things- she made them feel safe, I made them feel adventurous. Working with Kim was the best.

With so many different styles/methodologies/tools in development is it hard to decide what to teach new students? What criteria do you use to choose what will become part of the curriculum?

A thing it took us a while to figure out is that the technologies don’t actually matter that much, just what you do with them. We switched from assessments like “build an angular directive” to “use component-based architecture to build an app that does X/Y/Z,” and it had a bunch of cool benefits:

  • It gave us the flexibility to change with the times without also having to rewrite assessments every other month
  • It gave students agency- never underestimate how powerful it is for someone to feel like they have a choice, even if it’s just between react, angular, and vue.
  • It diversified our graduates, so we weren’t just pumping out 30 cookie-cutter students every 6 weeks with identical skillsets
  • It encouraged a lot of them to experiment with multiple technologies by structurally highlighting how trivially stuff in the same category is. A single student might have some experience with React, Angular, Go, and Django by the time they leave the program, which also gives them the confidence that they don’t restrict themselves to the exact thing that they studied in school.

There’s another, more macro side to that question though, and it’s a lot tougher

At some point, there’s only so many days in a program, and adding something means taking something out. Back in September, we reevaluated the content of the program and rebuilt it from scratch. We used a variety of public research in choosing what went in (most notably the NYC Tech Talent Pipeline report), we wrote assessments for those, and worked backward from there.

This was super controversial. Every report talked a lot about soft skills, and we knew empirically how make-or-break that was to a student’s job success as well. Taking out precious weeks of hard skills to make people go to meetups, network, run meetings inclusively, talk to clients about requirements, do presentations, and learn project management skills was not universally popular- especially since it came at the cost of deep OOP stuff and some of the wonkier CS concepts. For certain developers, that stuff is sacred cornerstones of the craft. All of our research showed that employers didn’t actually care about those things as much as they often pretended to, so we leaned on the research. No regrets, I still think it was the right call.

Would you rather fight 100 duck sized horses, or one horse sized duck?

One horse-sized duck. To quote an internet hero:

Anyways, I wanted to address some concerns some people have with my theory that a human with brass knuckles can beat up a horse. This theory is based on the idea that people can beat Dark Souls bosses while taking no damage just by running and rolling, things any moderately fit human is capable of. Add that to the fact that horses are far weaker than Dark Souls bosses and it’s hard to imagine how a smart and patient gamer isn’t a horse’s worst nightmare.

I don’t like my odds as well with 100 of just about anything.

What’s something you believe that other people think is weird, or alternately that you think other people think is weird?

I value responding to change over planning. Planning is overhead and has a cost. If you can develop the discipline to:

  • Stay calm under stress
  • Defer decision-making until you can’t anymore
  • Search for opportunities and threats in real-time
  • Pivot early and often

The speed with which you can move will give you an advantage over a meticulous planner. They may look composed as they confidently march to the wrong solution and you may look foolish bumbling your way to the right one, but agility beats prediction every time.

Why did you get into music? Why did you get out?

A few things stand out:

  • When I was in elementary school (early 90s in grunge-era Seattle), it seemed like music was culture, and it felt powerful and vital. It was a way to express yourself, it was a way to be cool, it was a way to conjur something out of nothing. I dorked around a little on keyboard and guitar and clarinet, but I always felt like I was investing in being able to make culture.
  • When I was in 6th grade, the coolest people were in jazz band, and what they were all doing together looked so cool. I was too young for it, but I took home their sheet music and memorized all the alto/tenor/bari sax stuff, and they let me in, and it was exactly as awesome as I had hoped. I still remember the smell of that room.
  • When I was in 7th grade, I took this weird class with no structure and no curriculum- you just got to be in the band room and do whatever you wanted with the space. It was perfect- I learned to play drums and guitar, I transcribed songs, I wrote stuff.
  • The first time I saw Reel Big Fish in 8th grade, I decided I wanted to be the guy on stage creating that energy in the room. I started my first band that year too, which in retrospect was an awesome peer leadership experience more than anything.
  • Throughout high school, it was just my life. I was the drum major of the marching band, I played in a punk rock band that played Warped Tour 99, I was in a latin jazz band, a percussion ensemble, a bunch of choirs, musical theater, a boy band, a bunch of one-off bands. I also got into recording then, which seemed like a sensible thing to do. I was “the guy” for doing records for local bands, and I (mostly) paid my own way with that stuff.
  • I got a degree in audio engineering, which was a great experience, but a tough business. It’s as feast/famine as they come, someone else became “the guy” for local records (fun fact: he just got a grammy for the last Portugal. The Man album), and I was literally staving. I played in a moderately popular local ska band, but it didn’t feel as good as I imagined it would.
  • I moved to Las Vegas and took a break from music entirely for a few years, and got deeply depressed. I eventually got fired from a sales job for drawing scale diagrams all over my desk. I got a job in pro audio sales at Guitar Center in Englewood, and mounted my big comeback.
  • I loved gear sales and moved into management at Guitar Center quickly. I was with people who understood me, and thought I had something valuable to offer. I played in bands, I taught lessons, managed a music school for a while, and became a marketing manager for pro audio companies.

As for why I got out:

After all of that, I was paying my mortgage well enough, but I was stressed. I generally had 3 jobs at any given time, and that’s not an industry where you ever say no to work- you might be without anything for months, so you do anything and everything. It was exhausting, and really hard on my marriage. It also wasn’t really fun anymore, but being that close to all of it, I just thought that meant the world was unjust. I thought I was built for one thing, and I was cursed because I had to struggle so much to exist.

My wife and I wanted to start a family, and this was all looking like a non-starter, so I went back to school for information systems. I did some database stuff in Las Vegas and had an aptitude for it, and I liked sales and marketing, so it seemed like a reasonable enough fit.

It turns out that I actually like building teams and software a lot more than I liked music. So many of my career decisions were made by a teenage boy. The music industry aggressively reinforces the “no one but us will ever understand you” nonsense, so it was really surprising to me that I dug software as much as I did.

Post script to all of that: I did a 12 year reunion with my old ska band last year, and I’ve been doing a lot of writing lately. My time in music gives me a really unique perspective on building products, and it’s fun to just make music because I want to now. It all worked out, no regrets.

What’s your favorite computing device?

It was the Chromebook Pixel 2. The hardware design of that thing was perfect, and while the Linux integration was quirky, it was still pretty damn good. I’ve only gotten to play with the new one a little bit, but it seems nice as well. That’s the only computer that I’ve just been happy to use because I liked touching it so much.

I’m currently typing this on an XPS 13 with Ubuntu/Budgie. I like its power and screen, but I don’t like Most Things about the design of it.

Everything in its place, or the opposite of that?

Mostly the opposite. My general philosophy on such matters is to not try to organize/categorize/automate anything you don’t understand. Unless you do it the exact same way every time, you probably don’t understand it well enough. Some things I do the same every time. I eat and wear the same things every day, so there’s a system for that stuff. I don’t follow any predictable pattern with where I work or what I work with though, so I have spare chargers and pencils and books and stuff strewn all over the place, and prefer it that way.

One more related thing: I also try to have relatively few things, which I think helps. If something’s missing, there aren’t that many places it can be. It’s probably time for another purge, but I get a lot of joy out of discarding stuff that’s done its job.

Any relation to Aaron Coberly?

Yep! He’s my cousin, and he’s a terrific guy. I’m also (unsurprisingly) related to his son Caspian Coberly, who’s a guitar prodigy and is pretty active in the Seattle area.



Kyle Coberly

Educator, business dork, software developer. kylecoberly.com

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