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Human Skills 016 - Magical Teams
with Jason Reid
Jason Reid started his career in the defense industry, handling servers and software for Lockheed Martin. He moved into data engineering in the early 2010s, and then on up into leadership, becoming a director of data science and engineering at Netflix, and now the cofounder of Tabular, a data automation platform.
Our conversation went in a bit of an unexpected and serendipitous direction. We started talking about what makes for a good team environment, and realized that we've both had experiences with teams that seemed magical - hard to predict, filled with intangibles, but the best experiences of our working lives.
We covered a range of other topics - deliberate practice, transitioning to leadership, and more - but we kept coming back to this question of "magical teams", what made them magical, and how we are both searching in our careers to find or create that experience again.
How do you identify what team and environment is going to be good for you?
Yeah, that's probably a lot of self-awareness, a lot of trial and error. Being honest with yourself about what's worked and what's not. If you work in these little pods long enough, I think almost everybody I've talked to can think back through their career, even if that career is only five years long, but certainly as it gets longer than that... And they can point to pods that they were extremely happy, at least from their perspective or... you know, performed in and operated in a super healthy way.
And they have counter examples as well. But I feel like at some point, we're constantly chasing getting back into one of these environments that we've had, for some fleeting amount of time that we just, which felt so great.
And it's always a bit fleeting and you kind of know it, like, you know it's not gonna last forever because change is inevitable. So when you're in one of those situations, you just relish it and you hope it lasts for as long as it can. And when you're not in one, you're always just trying to get back to one.
I feel like that's the sort of the cycles of career and software development. And yeah, how to know if you're gonna be one of those things. I think that's incredibly hard. I think you can have a sense of the types of groups you're gonna match with. Like for me personally, I'm like a highly collaborative person. I want interactions, I want shoulder taps. I want us to whiteboard everything and talk through it.
But not all groups want to work that way. I also want very direct communication. I want you to tell me when my work sucks and I want to do the same for you... not that it means you as a person are not great, just that this particular thing that you did wasn't as good as it could have been.
So I know that about myself and those things are definitely key ingredients to getting in these magical situations. I think that I call them magical situations because there, I think are these intangibles that are kind of impossible to know until you get in them. Like these group dynamics that happen that are really difficult to predict. You only know it when you're there.
How do you create a 'magical' team environment?
I think that's a full-time job in and of itself. I also think it's, at least for me, more challenging in an all remote environment. So in our current world is an all remote company. We're all spread out. And as this person who wants to be highly collaborative and shoulder tap and whiteboard, like that stuff doesn't work super well in an all remote environment.
And so I think I definitely miss the in-person dynamics quite a bit. And I think I'm still very much on a journey myself and with our current team on how to get back to some of those magical states in a remote world. Is it even possible? I don't know that I can yet point to an all remote team where I felt that sort of feeling. I'm like, "oh, this is magical."
I mean, I think there's lots of great things I can point to about our current team and pods and how they operate. But to your point that you can think back and sometimes there's something special about certain interactions and it's not obvious what made them that special.
So if I can't be a wizard, what are actual real tactical things I can do to at least help build pods that are successful in what they're trying to do in an all remote world? Certainly that is matching, to your point earlier about matching company culture. What kind of culture do we set at this organization? Can we find other individuals who match and enhance and enrich that culture?
And then you just get into the very nuanced conversations about matching versus also bringing new perspectives Because you can be overly matched. There's also a thing, like too homogeneous of a pod is also not the best outcome.
If you think back on the ones that were great, they always had some amount of heterogeneity to them. They were people who came from different backgrounds, different perspectives. So that's part of the magical formula for sure.
At the same time, there are people who clearly just don't fit and that can be really toxic for a group. So finding that balance I think is hard, but I think you certainly look for folks who you think are gonna match on some of these dimensions. How do they communicate? How do they wanna collaborate? Are they passionate about the work that they're doing? I think those things being matched on some of those attributes, I think it's really important as a starting point.
Are there skills you deliberately practice outside of work and then bring back to the workplace?
Yeah, I think so. In particular... Being able to try and see a situation from as many perspectives as possible in the most objective way possible. I think that there's many opportunities to do that inside and outside of work and that can be super helpful.
Even with my kids sometimes, they'll come home and they'll be complaining about something that happened at school and like, "hey, let's go through an exercise of looking at this from as many perspectives as we can. what do you think the teacher thought about this? Or what do you think your friend thought about this? "And like, let's put ourselves in their shoes and let's just talk through it.
Maybe that's also hopefully good for them as young people to learn to do that. But I think it's also just a good exercise for me. Like, let's practice that. What would that look and feel like? Let's talk through it. There's lots of opportunities to do that.
And I think that getting good at seeing a problem from multiple perspectives and being able to put yourself in other somebody else's shoes, those cliche things. But they're really important when it comes to leading teams and just work with people in general.
Without necessarily compromising on things that are important to you or important to the team's success. So it's okay to see things in many perspectives. I think it's still important and necessary. Especially leading a team that you have to find ways to go forward and be successful. And there's things you can't compromise on.
What are the lessons you wish you had known moving into leadership?
There's two and they're related. You can be more effective by letting go of more things. As a leader, the more things that you can let go of that you can not be indirectly responsible for actually increases your ability to be an effective leader and to get a group of people to get more things done.
And that's very contrary to individual contributing where it's just like "the harder I work, the more I will get done." And it's a very like 180 mindset to be in. And that was a very difficult transition as somebody who like prided myself and all the stuff that I could get done, which was sort of like makes you stand out, which is a weird thing about how we raise our top performing ICs to be leaders, because it doesn't actually match up very well.
And the second part of that is related is like how I would get job satisfaction, how I would be satisfied with the work that I was doing, how I could look back on my days and feel good about what I had accomplished when it wasn't me directly accomplishing these things and getting these things done.
So those two transitions were really hard... continue to be difficult for me. And maybe I should have known that going in, but it actually... wasn't maybe as obvious as it should have been in hindsight, that that was gonna be the case.
How do you think about delegation?
I think the analogy here, which is overused, but resilient for me is how I approached coaching. I had played collegiate athletics, I was a volleyball player, and then I did a bunch of coaching young people throughout my career as well.
And there it was easy. My playing career was over. I was clearly a coach now. And so... I was getting satisfaction and evaluating performance on the performance of the team. So I didn't have this weird thing where I was the one who should be out there playing because that wasn't even an option.
And so when I was thinking about it through the coaching lens, it was... how do I ensure that I take the strengths of all the players, combine them in a way that as a group, that we are better. Super cliche stuff, but I think still very true things. How are we better together than we are as individuals? And so that means playing to our strengths, all of our strengths and making sure that people are in positions which allow them to leverage their strengths and then hiding our weaknesses to the best of our ability, letting other people's strengths cover our weaknesses and so those don't get exposed.
And when I came to leading teams of engineers through a similar lens, actually it worked relatively well for me, it got a lot better. And so in thinking through like, I'm not gonna be the one doing this stuff. How do I make sure that I set up and break out the work such that people are playing to their strengths, mostly covering their weaknesses. At the same time, just like as a coach, you are expected to help everybody in the group improve.
Part of your team success is everybody improving. So it's not about hiding weaknesses and pretending they don't exist. It's about covering them, but also... closing those gaps over time. So those weaknesses don't exist anymore, and it's about taking strengths and doubling down on them and making them even bigger strengths. So all those things are still true. And I think those same principles certainly apply when leading teams of people through, for software engineering at least.
Do you have approaches you use for managing your emotions?
Yeah, I'm sure there's always ways that we can do better. I think naturally I'm a pretty steady, pretty happy, optimistic person by nature. I think I am naturally inclined in a way that works. So that helps.
And then on top of that, I certainly lean on my partner a ton. We have a fantastic relationship, thank goodness. And they help me stay happy or at least a place where I'm able to talk through situations that are affecting me negatively to help sort of right the ship. So that support network, whatever that support network might be... like any human, those support networks are super important.
And ones that are outside of work. I mean, you need your in-work support network for sure, but you definitely need your out of work. That can be in the house. I have some, some great friends as well, that I lean on.
I think taking mental breaks is a, is a really big part of that story. I've been pretty good, I think in my career about giving myself breaks from, from work. I probably average six, at least maybe weeks, you know, a year, maybe more than that, out of work. Regardless if I was in IC or in high level leadership roles, but I think maybe people expect that you can't take as much time when you're in these bigger roles. And I just, I really combat that. I disagree with that completely. And maybe it's the reverse. You just have to take more time. And that's good.
And at a place like Netflix in particular, where the sort of unlimited vacation policy and you know, whether that's draconian or not, I don't know. I think it is what you make of it. I certainly, I tried to use that to help keep my mental state healthy and I got a lot of support from everybody at Netflix. And then we do the same thing at Tabular. We don't have a fixed policy. It's like, "please take what you need to be healthy and effective." And I try to model that for the rest of the company by taking time when I need it. And I do need it, absolutely.
On the search for magical teams
I'm glad we got into this conversation a bit about what makes these certain team interactions really amazing. I've read a bunch of the books and management books and team, and there's lots of good tidbits in there, but nothing that I've ever been able to pattern out to say, "Oh yeah, that's the thing. If I take that nugget and I reply it historically, That was the big unlock for why that happened."
And this is true, whether it was professional teams or athletic teams, all of it has this magical quality to it. I don't know what... actually if we ever could figure it out, probably we'd be bestselling authors or something. But it's really fun.
And I think maybe part of the fun of it is the search for it. It's sort of like you get to go on this hunt and journey in your career, and then once in a while you find it and it's magical, then you lose it again, then you just go searching for it again. So maybe it's meant to be that way. It's a bit of this treasure hunt that we're always on.
And yeah, I think some folks maybe haven't experienced that or think they need try to force their current situation to be that. I think I at some point learned that sometimes change is really the only way forward. Don't continue to force this if it's not working. It's okay.
It always seems in the moment that change is going to be really detrimental on one vector or another. And that never tends to turn out to be the case. Maybe some things were better, some things were worse. Sometimes it's great.
But yeah, I think I've learned to be less afraid of change, even when things seem like they're going well. Humans are really adaptable. More than we think.
Links to Jason
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