Discover more from Attainable Newsletter
No territorial boundaries
Kelsey’s favorite place on earth is earth, and it reflects his sense of team and community.
“You know, these days I'm just happy to be on Earth” he says as I ask him where he enjoys being the most. “I don’t stick to the territorial boundaries anymore, you know, I was just in Australia a few weeks ago, I’ll be in Stockholm soon. I know people all over the world, so I feel like a global citizen at this point”.
Kelsey makes a point about being a part of the larger community in a number of ways and I learn later that he was influenced with this sense of team by a high school coach. He says over the last decade he’s seen the world, and meeting people has made him feel more connected globally. “I feel like Earth is just one big city in the larger universe.”
A Pole Vaulter
Kelsey told me a story about his time on the track team in high school. His coach told him he was going to do the high jump event. He laughs as he says “I’m like, dude, I’m not that tall”. Then his coach added that he was also going to do the pole vault. “Now we’re getting ridiculous!” Kelsey screeched.
His coach explained that track and field is a team sport and that the objective is to accumulate the most points. It doesn’t mean perfection in every event, just that you show up. His coach seemed to have a sense of Kelsey’s drive and team orientation and he describes this as a quality of good coaching.
So the other element of great coaching is understanding different people, need different things. I'm already ambitious, I'm already self motivated and willing to learn new things. What I need is someone who sees the bigger picture, including the things I’m unable to see, and help me get to the next level. And so for me, as an individual, that has been what I really enjoyed most from a coach.
Turns out it’s with this sense of team and community that you’ll find Kelsey tackling all the latest tech he finds. He does it because he knows he can bring the whole team of us to a better place, even though he is maybe not the most likely to be in this role.
If you follow Kelsey on Twitter long enough you’ll find tweets like this. He dives in and shares everything he finds. This is another example of him “pole vaulting” for the rest of us.
We’re not robots
Kelsey has a strong philosophy that says all of us are human beings before we are software developers. He believes we mistakenly come to work and try to take away the fact that we are human. “I’ve got to write this much code by this time. I have to do things in this way, because that’s the way we’ve always done it” he says as he describes how we lose the ability to be creative. We lose reason and motivation when we drop to the lowest denominator robot level.
He adds “if we are willing to allow the whole person to do these jobs we’ll get better outcomes, which can be hard if everyone else is acting as a robot, because robots are programmed to work a certain way, and tend to reject things they are unfamiliar with”, so he believes strongly that we need to be treated uniquely and coached in ways that are specific to our talents and abilities.
When I was an engineering leader, or someone's manager, that was my strategy. Listen to them. Learn what they're good at, understand what really gets them going, step back and say okay, I'm gonna craft something specifically for them. I'm going to set them up to leverage the unique attributes they bring to the table. That's gonna help them score points for the rest of the team, and the team will take notice, and be like, “Wow, you're doing the thing that we knew needed to be done, but none of us did it.”. Now their perception within the team is much better and they also gain respect from their peers.
The topic of science vs. art came up when I mentioned that sometimes our jobs require us to be very scientific and on some occasions that gets us stuck in just the science we know (robotically). “You need both,” he responds. He believes that we should be driving towards facts and experience. The truth is at the heart of that. “So if you’re after the truth, then curiosity is what gets you asking questions, and the scientific method helps you test and apply what you learn.” Kelsey goes on to describe how sometimes we fall into robotic traps, and that we ought to be sure to continue to seek the “why” for our work.
I think people forget that curiosity is often the initial input into the scientific method. As an industry we tend to create roles so rigid that we often outsource curiosity, and ask people to wait for someone else to show up with a list of requirements, which we just blindly attempt to fulfill, and at that point, you're just doing what you're told. Like a robot.
I asked Kelsey what he thought about our industry and our ability to say “I don’t know” in situations like he mentioned, or if he thought we’re still stuck in the idea that we should be the experts in the science of it all. As you can imagine his response was very team oriented and he included product owners and project managers in his response.
It takes a team of people to build this stuff. They need various skills. Some people are really good at operations, some people are good at writing code, or pricing products, I could go on and on. When you bring groups like this together, I think the number one goal is reaching a shared understanding of the problem, which will serve as the foundation for the solution. If you're gonna build a house, then I can see people asking for a rendering of the house, or a blueprint, so they can be sure they understand exactly what you want to build. This shared understanding allows people to say: “Okay I'm gonna put up the walls, but after you lay the foundation, this should take about 3 months”. That’s the part I often see missing, shared understanding, most people have never seen the blueprint, they are just patching holes in the wall. In the real world we call this lack of vision.
Kelsey’s idea of shared understanding is a critically important quality to successful teams. He points out that it’s really easy to lose teams without this. If we just fall into line robotically, we end up with a situation that provides no real outcome. Just visionless inertia.
And so when a team lacks vision, you get this weird situation, we've all seen it. You got a team and everything's going well. People come and go over time. And then eventually one day you ask “What are you all doing? Why are you doing it that way?”, and they answer, “I don't know. I just got here. This is how it works. I'm just trying to fix this small bug, not rewrite the whole application.” People start to lose sight of the big picture, now everyone is just churning out stuff, creating technical debt, but they have no idea they're taking out loans, because they stopped paying attention.
As we moved on from robots, we started to talk about the qualities that make us human and it turned towards accountability and trust. Kelsey - again - has a very clear team bias for these qualities and feels there is a necessity to trust folks on your teams to do their very best, and that they hold the accountability to do their best. And he was quick to remind me, “and if I'm gonna honor that trust then I'm going to bring the best of my abilities to each situation. Even if the code I write isn't quite right, people know I gave it my best effort, and know I’m willing to learn from my mistakes, and get better over time.”
Kelsey also described how to use moments, even as small as code review, to improve trust.
I see code reviews as an opportunity to teach and learn. It’s a way to watch people learn in real time, see them grow, and see their best get better. It’s also a way to build trust, especially when you see people’s code improve over time. That's what all healthy teams have – trust.
Earlier as Kelsey was describing the pole vaulting conversation he explained how his coach told him that it wasn’t a matter of him being the best pole vaulter, but that it was another way he could contribute to the team.
The best coaches see something in you that you didn't see in yourself and set you up for success. So when I look at that, from the software development perspective, great engineering leaders are able to do something similar.
Kelsey is very clearly driven by seeing growth. He believes great coaching includes seeing more in people than they see in themselves, then setting them up for success and he practices this in real life a lot.
The topic of helping as many people as possible came up, and Kelsey was quick to say that he prefers impacting one person at a time and letting that scale out to others. He believes we’re all capable of helping others grow. And when dealing with just one person at a time, he says he encounters people asking him how they can be just like him.
They'll always ask “Kelsey, what, what do you do?” I say, look, I could tell you what I do, but this isn’t about me – I still share my secrets because you can always learn from others, but I don’t miss an opportunity to help them understand what makes them unique – So, tell me a little bit about yourself and let's try to fine tune something that highlights your unique attributes, and then leverage those things to help you reach your goals. I love watching their eyes light up afterwards.
Oftentimes, people still want to mimic some of the things I do, they're like “yeah, but, I want to give talks like you do, so how do I be as good as you?” I'm like, well, I just work on being a better version of myself, and if you want to be like me, then you’ll need to get better at being you.
There is a humility to Kelsey that is very up-front and in your face. Here is an extremely respected personality, and massively accomplished engineer, and yet, you find him remaining at your level.
You never want to be that person. Standing at the podium telling someone else that they should be this, or they should be that. Maybe that’s why I don't refer to it as coaching, I don't even like to call it mentorship, because I’m just sharing my lived experiences. I walked down that path, and I fell in a hole, so if you're gonna walk down that path, then watch out for the hole.
I was struck by this because my favorite West Wing episode Noël has an ending in which the character Leo McGarry tells Josh Lyman a story about a man falling in a hole, and finishes by saying “as long as I’ve got a job, you got a job, you understand?” I can’t help but see Kelsey supporting other developers just the way Leo supported Josh in this episode.
Kelsey shared a moment when his past boss helped him grow, but framed it in a way that he understood he was supported. He said that not everyone is the same, but for most people they just need help seeing it in themselves. His boss said to him:
Hey, Kelsey look, I know this may be outside of the job description, but what do you think about this particular opportunity? Would you like to take something like this on? Here's the expectations on it. I know it may be a stretch for you, but I'm here to support you if that's something you're interested in.
On Twitter, and in all of his conference presentations and famous demos, it’s crystal clear that Kelsey believes everyone has potential for growth. Sometimes it’s uncomfortable, but it can always be accomplished with a team, holding accountability for each other, trusting the process, and sharing a vision.
Taking the time
I asked Kelsey if there was a point of time, or a line to which you stop coaching, especially if you feel that the person just can’t be helped. He said “my line is probably way too far, you know, to me, if I have the time, I'm gonna try my best, straight up, and I've seen it work. And I've seen it, not work, but I'm okay if it doesn't work, but I do think it's worth the effort, that’s where I fall on that.”
Kelsey then gave me a lesson, that in my white privilege I simply would not have gotten in my own experience, about spending time with people and allowing them grace to make mistakes while being authentic and growth minded.
I've been called the n-word on Twitter before, like “Kelsey, that n-word!” You can imagine the responses from people seeing that: “I can't believe this is happening to you.” A fews months later, I remember this guy, DM me and said “Hey, I was the person that said that to you on Twitter. I was going through some things at that moment.” I’ve got two decisions. I could ignore this person and tell him to F-off. Or I can be empathetic and say look, and I told him the truth, I was never mad at you. I already know there's a part of our society that, for whatever reason, has those views, so I'm not surprised. I'm not naive. But what I am happy about is that you now realize that that's unnecessary. Now if you want to make things right, you probably know someone who probably holds similar views, go and try to help them move past this unnecessary way of thinking. Some people ask, “Kelsey, why do you spend all that time? It doesn't scale. What's the value of doing all of that for just one person?” To me, there is value in a single person becoming a better person. They made a mistake. They’re not banned for life. People like me can have a conversation with them, but I'm going to hold them accountable, and expect them to do better going forward.
There is a trust and empathy in Kelsey’s words that I find honorable beyond measure. It reminded me that in my position I can do more. And maybe that was his point in our conversation too. Maybe he was indirectly coaching me, and that in this hour of conversation I was the “one person” he could help. He finished with:
Little things can actually change the world, and so I never miss an opportunity to make that happen.
“I’m definitely a pencil person because I just don’t believe in permanence” Kelsey responds as I ask him if he’s a pen or pencil person. It’s one of my favorite questions because so many people have different feelings about it, and they all distill down to how we treat mistakes. While talking with Kelsey you firmly find a person who is OK with mistakes and moving on, but with a pencil, so that you can erase the mistake and replace it with the correction. It’s an inspiring take on the question because it’s not a perfectionist view, rather a position that allows for change and growth.
Facts and experience
One of the most impressive parts of the conversation was early on in the hour, and came out of my question about how Kelsey sets up his environment when he wants to put fingers to keyboard and write code. I ask this question because I am intrigued with how we create our space that we work in and what helps inspire us to get work done. What I received however was a complete and perfect framing for how we should work together to improve our shared experience.
Kelsey began by saying “I start by myself, you know. I gotta try to figure it out by thinking.” And he then described the relationship between facts and experience that shape our opinions.
Facts are facts, they might even be true, but that's all they are. We are humans, not robots, context matters, and I think the world appreciates opinions. Opinions should be a combination of facts and experience. And even though the facts say this may work, or should work, my experience says it doesn't work under these conditions. A lot of people really need that additional context to understand things. And so for me, I create space to gain experience to help me understand the facts. Trust, but verify. So if you tweet, we're doing Web 5, that's probably a fact. And you link to some doc, okay more facts. But now I gotta go get that experience, by giving myself room, giving myself time. Get my hands dirty, and then when I show up with an opinion, which people tend to appreciate, because my opinions are rooted in authenticity.
He also added that there are plenty of occasions when he needs feedback and he’s comfortable reaching out on Twitter to ask questions. While he likes to be alone in silence to absorb the material at first, he says if he’s still confused he has a great professional network.
And if I'm still confused, I've been so fortunate to have a really great, professional technical network that I can just go on Twitter and be like “Hey, here's what I'm thinking at this moment”, and when I don't know, you know, people like to be right. The swarm will show up. They let me know if I’m thinking about things all wrong, or if I’m exactly right. And then my DMs will light up with people offering time for a one-on-one, then I get to have a conversation, and oftentimes it's with the people who invented the thing I’m asking questions about!
Team and community
As Kelsey mentioned, his favorite place is Earth. I understood what he meant in a particular way after he said it. It sounded like he was saying he loves everywhere he’s been and where he’s going. But after our time, I came to understand it in a different way. I believe he means that the earth is a big place, and that as humans, we don’t have to take on everything by ourselves, and that we should work as a team and a community to help each other. He believes that coaching is seeing the best in people and reflecting it back to them, and giving them the support to grow. And the best way to do this is to not create territorial boundaries that keep us apart.
It was a great pleasure to talk to Kelsey, and I have to admit that at first I was unsurprised he accepted to talk with me, because well, he literally talks to everyone! While it’s true that he’s selfless with his time, I now understand the real gift he gave me was thoughts about trust, and taking the time with people, that on their face are pretty obvious and standard ideas. But coming from him with his facts and experiences, holds a special power. In this city in the universe named Earth, I’m so glad that Kelsey is on our team. Thanks Kelsey!
This is the second in a series of profiles in software. If you enjoyed this subscribe to continue getting the series. I’ll be writing profiles of industry leaders and interesting people from all areas of tech every month.